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Fun Local Spaces with Live Music in Charlottesville

Charlottesville is a little town with a big appetite for music and arts! Whether we’re cheering for world-touring artists at the John Paul Jones Arena, or just feeling the mellow vibes of a local group, there’s always someone playing something in C’ville. The Visit Charlottesville website has a “Concerts & Live Music” page which keeps track of new and exciting events and acts coming to town.

That said, there are so many opportunities to enjoy smaller performers all around this area any day of the week. Often, they’re playing at fun, casual venues that can combine music with food, drinks, or outdoor ambiance. Here are some of our favorite places to enjoy live music in Charlottesville!

Carter Mountain Orchard

There’s no denying we’re partial to our own venue! Carter Mountain’s Thursday Evening Sunset Series is a Charlottesville tradition, and visitors are welcome every Thursday from April to September to savor the sunset from above town. Grab a spot at a table, spread out a blanket, or dance the dusk away, it’ll be a good time regardless!

There’s a new band every week, a variety of food trucks, delicious Carter Mountain Wine, Bold Rock Hard Cider, and the best view you can find at any music venue we’ve heard of. So it’s worth making the trip up the mountain multiple times while you have the chance! We even have season passes available if you want to make it a weekly habit.

The Downtown Mall

Charlottesville's downtown mall at evening.
Photo from Charlottesville Albemarle Convention & Visitors Bureau

The pedestrian mall is a great space to hang out, shop, or grab a bite, and it’s also a prime source of nightly live music in Charlottesville. The Whiskey Jar features live music almost every night, with regulars like Betty Jo’s Boogie Band on Mondays. Wednesdays and Thursdays have live samba, rumba, and Latin guitar at The Bebedero, while Miller’s has jazz on Wednesdays, Thursdays, and Sundays. For more of a concert venue feel, The Jefferson regularly hosts big acts and dance parties. The Southern, by contrast, has a more intimate, indie stage feel.

Lots of restaurants and bars have one-off or impromptu performances, so if you have time beforehand, it might be worth taking a stroll and seeing what’s playing! For a more detailed list of smaller performances, check the Cville Scene.

Local Wineries

Chiswell Winery visitors enjoying live music in lawn chairs.

For a more relaxed live music venue, wineries offer comfortable spaces out in nature—and wine, of course! If your ideal live music experience includes chatting with friends and enjoying a drink or two, Charlottesville-area wineries might be perfect for you. The Monticello Wine Trail boasts beautiful mountain sunsets, crisp Virginia breezes, and wineries that are as well known for enjoyable atmospheres as for their award-winning wine.

Just south of town, Eastwood Farm and Winery has regular performances in their Barn venue, including dancing on Saturday nights. The historic Jefferson Vineyards features acoustic performances Friday evenings and Sunday afternoons. Keswick Vineyards features live music every Saturday, as well as their Wine Down Wednesday series. And near Crozet, all summer long our sister venue Chiswell Farm & Winery features both their Summer Sundown series on Friday evenings and afternoon performances on Sippin’ Sunday. If you’re coming to a Chiswell performance, we recommend packing a picnic to go with your wine!

College and University Concerts

The Charlottesville Symphony performing at UVA's Old Cabell Hall.
Photo from the Department of Music, University of Virginia

Every school year, Charlottesville’s population grows by a lot, and there’s a good amount of world-class musicians among those students and faculty! UVA’s Department of Music features over a hundred concerts every year from dozens of local and visiting ensembles. These concerts are perfect ways to show visiting relatives live music in Charlottesville while touring the University’s gorgeous Grounds. It’s not just classical music either, with jazz, choral, and even a computer ensemble performing throughout the year.

Neighboring Piedmont Virginia Community College also boasts a full-featured performance season, including dance and folk music. While both schools have more traditional sit-down music venues for quieter performances, their beautiful outdoor spaces and convenient locations mean they’re a relaxing way to spend an evening with friends and family.

The Ting Pavilion

The Ting Pavilion in downtown Charlottesville.
Photo from Charlottesville Albemarle Convention & Visitors Bureau

Located at the east end of the Downtown Mall, the Ting Pavilion is an iconic Charlottesville landmark that frequently hosts out-of-town bands and local acts. Its unique blend of covered seats and lawn viewing combines the best of open-air and interior concerts. Best of all, being on the Downtown Mall means you can count on dinner and a show!

Fridays After Five is a free concert series that runs all summer, starting at 5:30 PM. The musical acts are local artists, and concessions benefit local non-profits, which is why Fridays after Five has a well-deserved decades-long reputation as a Charlottesville institution.

Crozet Breweries and Orchards

Visitors at Chiles Peach Orchard during an evening concert.

Grown from a rural farming community, the small town of Crozet is a unique cultural destination just west of Charlottesville. The famous breweries and orchards that pepper Crozet’s lovely Blue Ridge foothills also regularly host local and out-of-town musicians. Whether you call Crozet home, or you’re planning an impromptu evening out from Charlottesville, it’s a music-lover’s place to be!

When it comes to brewery gigs, the Main Taproom Stage at Pro Re Nata is a well-loved, exciting evening venue on Fridays and Saturdays. Starr Hill Brewery enjoys weekend music as well, plus regular Sunday afternoon performances. If you’re looking for more of a family vibe, Henley’s Orchard features semi-regular live performances, especially during HenleyFest in fall. Chiles Peach Orchard has live performances from 1–4 PM, May–October, every Saturday and Sunday.

An orchard is an especially fun place to enjoy live music near Charlottesville, because there’s so much to do! Spaces without concert ticketing like Chiles Peach Orchard have a drop-in, drop-out atmosphere perfect for grabbing a snack, playing an outdoor game, or even picking your own fruit before, during, or after the performance. An afternoon visit to a Crozet brewery or orchard could easily turn into an all-day adventure!


Charlottesville might be a quiet city most of the time, but we get loud when we want to! So make a plan to see some live music this week by check out our calendar. There are all sorts of events being planned at Carter Mountain and other Chiles Family Orchards that might catch your fancy. We hope to see you soon!

Wineries to Visit on the Monticello Wine Trail

In 2023, the Monticello AVA was named Wine Enthusiast’s Wine Region of the Year. This prestigious recognition comes at a time of momentum for Virginia wine: local winemakers’ understanding of the cool-climate terroir results in delightfully unique vintages and a blossoming community of wine lovers.

Aficionados with an affinity for California chardonnays and Tuscan Chiantis may ask: what makes Virginia’s wine so special?

To start, the area’s wine history dates back to the 1700s, when former President Thomas Jefferson spurred the beginning of American winemaking. While Jefferson’s attempts were nearly fruitless, recent generations are realizing greater successes.

The area’s bountiful vines of cabernet franc, petit manseng, petit verdot, and others are now hallmarks of the region. Many of the best wineries on the Monticello Wine Trail boast multiple award-winning wines of local competitions, including the annual Monticello Cup and Virginia Governor’s Cup. A special congratulations to the winemakers at King Family Vineyards, who took home the winning cup at both competitions in 2024!

2024 Monticello Cup silver medal wines

At the center of Virginia Wine Country is the Monticello Wine Trail, which connects over 40 wineries around Charlottesville. Member wineries share a dedication to crafting quality beverages and welcoming wine lovers to our beautiful state.

We’re proud to be members and share comradery with other family-owned wineries in the region. Of course, before we discuss some of the best wineries on the Monticello Wine Trail, we must introduce ourselves!

Chiswell Farm & Winery

Chiswell Farm & Winery is the most recent addition to our family of venues, joining Carter Mountain Orchard, Chiles Peach Orchard, and Spring Valley Orchard. Since opening in 2021, we’ve had the pleasure of welcoming visitors from near and far to our historic home-turned-winery in Greenwood, Virginia.

Having planted the first trees at Chiles Peach Orchard in 1912, our family is deep-rooted in the Crozet community. Now, our fifth-generation farming family has three generations actively involved in the production and distribution of locally-grown produce, including the wine grapes used by many of the area’s wineries.

One of the best parts of sharing our wine in this historic home is the unique spaces. Throughout the property, guests will find individual rooms where they can make themselves at home. It’s always a joy to see friends and family cozying up on one of the downstairs sofas or challenging each other to a chess game upstairs.

Five men sharing wine and snacks at Chiswell
Two women doing a sparkling wine toast at Chiswell

Of the many things that make Chiswell special, we take pride in our team’s creativity in developing different specialty drinks every season! As one of the few wineries in the area to do so, we’re always testing different combinations and finding new ways to enjoy our wines.

During the spring and summer of 2024, we’re mixing up a Strawberry Citrus Sangria, which features our rosé, lemon-lime seltzer, fresh strawberries, and a dash of mint.

Strawberry Citrus Sangria specialty drink

Septenary Winery at Seven Oaks Farm

Located three minutes from Chiswell

To find Septenary Winery, all you need to do is take a short trip down the road from Chiswell. Located on Seven Oaks Farm in Greenwood, Septenary is bustling with farm animals! Seven Oaks Farm sustainably raises free-range Pekin ducks and grass-fed cattle. While the livestock aren’t part of the Septenary Winery tasting experience, they are a testament to the Zimmerman family’s dedication to sustainable farming.

This commitment extends beyond livestock and translates into the family’s wine grape production, as well! Todd and Sarah Zimmermann founded Septenary to preserve and improve the fruits of their farmland. The Estate Vineyard is carefully placed to facilitate ample airflow, sunlight, and optimal growing conditions for seven acres of merlot, cabernet franc, petit verdot, syrah, and viognier vines. 

Three bottles of Septenary Wine
Vineyard at Septenary Winery

Pollak Vineyards

Located five minutes from Chiswell

Pollak Vineyards is the namesake of its founding family. Margo and David Pollak saw the potential to create quality wines in well-sited and meticulously maintained Virginia vineyards. This potential blossomed into their winery, which opened to the public in 2003.

We firmly believe that each vineyard’s wines capture unique qualities, from the caliber of the terroir to the grape harvesting methods, aging, and bottling experience. However, there’s something particularly distinctive about the wines at Pollak Vineyards. Pollak’s winemaking techniques are deeply influenced by European tactics, including those in France’s Bordeaux region. If rich and complex tasting notes characterize your dream glass of wine, then Pollak Vineyards is worth visiting!


Flying Fox Vineyard

Located eight minutes from Chiswell

Flying Fox Vineyards consistently produces a limited quantity of wines with the promise of consistency and premium quality. This portfolio features eight Virginia classics, including viognier, cabernet franc, and petit manseng. The winemaking team’s sharp focus on specific varieties encourages play outside the wine space. This is especially evident in the vineyard’s Vermouth production!

Flying Fox’s Vermouth label has four flavors, each highlighting the bounty of Virginia’s distinct seasons with botanical infusions. These Vermouths may be enjoyed neat or in a cocktail (or, as they call it, Fox-tail!).

Flying Fox vermouth
Flying Fox rose wine

Owners Emily Hodson, Elliott Watkins, Chloe Watkins, George Hodson, and Tralyn Hodson envision Flying Fox as a project-based winery with room for creative exploration in the winemaking process. Many locals may recognize the Hodson family name, as they’re the winemaking team behind…


Veritas Vineyard & Winery

Located 12 minutes from Chiswell

The Hodsons have deep roots in the Virginia wine community. Andrew and Patricia Hodson started Veritas in 1999. Twenty years later, the large operation now involves multiple generations of the family.

Located in Afton, Veritas boasts incredible views of the Blue Ridge Mountains and acres of grapevines. Whether you prefer to soak up the sun on the lawn or grab an indoor table, there’s space for groups of all sizes.

This winery is a must-visit for followers of Virginia LOVEworks. In Veritas’ indoor tasting room, there’s a LOVEwork displayed just above the wine bar, crafted from hundreds of wine corks. Visitors can admire the sign while ordering from the winery’s extensive menu. Snapping a keepsake photo makes for a beautiful memory of time well spent.

Veritas tasting room

While it’s true that the best wineries on the Monticello Wine Trail often boast awards (and yes, we have our fair share), what really sets them apart, in our opinion, is the warm welcome you get from a family-run venue. This is especially true for those with involvement from multiple generations; the more branches on the family tree, the better!

We hope you enjoy visiting these and other must-try Crozet wineries during your explorations through Virginia Wine Country. Next time you visit our Big Ash Bar, let us know what you think on Facebook or Instagram!

The Ultimate Charlottesville Bucket List

Are you visiting Charlottesville and not sure how to make the most of it? Or have you been living in town for a while, and you’re finally ready to explore what our area has to offer? Either way, we’ve got you covered with must-include entries for the ultimate Charlottesville bucket list.

Monticello

Photo credit: monticello.org

Thomas Jefferson’s life is intertwined with Charlottesville, from his birth in Albemarle County through his founding of the University of Virginia. Just two miles outside of town and next door to Carter Mountain Orchard, the home and estate he spent much of his life designing is open to the visitors.

Thanks to the Thomas Jefferson Foundation’s careful curation, you can experience the rich and complicated history of one of America’s founding fathers. The historic home, beautiful gardens, exquisitely presented exhibits, and activities for all ages are just a few of the reasons half a million visitors come to see Monticello each year!

Monticello Wine Trail

Image credit: monticellowinetrail.com

The area surrounding Charlottesville is home to over 40 Monticello Wine Trail wineries. This association of viticulturists work to fulfill Thomas Jefferson’s vision of Virginia wines taking their place among the greatest wines in the world. Most of the venues are open year-round. All provide a sumptuous experience of Central Virginia’s wine country, with its rolling hills and wines of national and international acclaim.

We encourage you to wander this trail at your leisure, and of course to make our sister venue, Chiswell Farm & Winery, one of your stops!

Downtown Mall

Photo credit: visitcharlottesville.org

When Charlottesville converted eight blocks of its downtown into a pedestrian mall in the 1970s, few could imagine how it would reshape the city for generations to come. The Mall is the place to be. It gives locals and tourists alike a chance to walk, socialize, and share a meal or drink, all in a space designed for that decidedly old-fashioned and charming way of getting around: with our own two feet!

Whether you come to dine, shop, or people watch, there are endless chances to enjoy yourself. It’s impossible to picture Charlottesville without the mall—and no visitor should miss it.

Fridays After Five

Photo credit: tingpavilion.com

The Downtown Mall also hosts one of Charlottesville’s premiere community events. The Fridays After Five concert series takes place each Friday, from mid-April through early September. Gather by the stage under the pavilion’s soaring white cover, take a seat in the grass, or just let the sound come to you from a spot halfway down the mall. There’s no wrong way to enjoy music or to mingle with the community that turns out. Oh, did we mention the shows are free?

Of course, if live outdoor music is your jam, you can also come to Carter Mountain Orchard for our Thursday Evening Sunset Series!

The Paramount or The Jefferson

When you want to soak up a little culture in Charlottesville, you don’t have to look far. Between the Paramount and Jefferson theaters, you’re spoiled for choice. The Jefferson boasts “the best live music in Charlottesville,” and the Paramount offers all things arts: plays, book events, stand-up comedy, classic movies, talks, concerts, and more.

No visit to artsy Cville is complete without a show at one of these historic venues!

Charlottesville City Market

Photo credit: charlottesville.gov

For a friendly bustle and a basketful of local food, look no further than the Charlottesville City Market. Hosted right beside the Downtown Mall on Saturday mornings from April through December, this farmer’s market has something for everyone. Fresh produce? Check. Local crafts, tacos, treats, and a generous helping of live music and impromptu conversations? Yup. From newborns in slings to octogenarian grandparents, you can find everyone mingling between its stalls.

You can find us there, too, offering your favorite in-season orchard fruits, plus pies, apple cider donuts, and more!

Riverview Park

While amazing hikes and natural spaces surround town (like the iconic Humpback Rocks,) Charlottesville boasts wonderful in-town options, too. Among the best is Riverview Park. With miles of tree-lined paved trails on one side of the river, and an unpaved trail on the other, this park is fantastic for a walk, a bike ride, a bit of bird or turtle watching, or a playground visit with the kids. If you visit during the summer, you can also rent a kayak or tube from Rivanna River Co. for a lazy river float!

Ix Art Park

The Foundation behind Ix Art Park dubs its indoor exhibit, The Looking Glass, a “permanent immersive art experience,” and we think that’s a pretty good way to capture the entirety of this fascinating Charlottesville fixture. Nestled among restaurants, a brewery, and a sake distillery, Ix Art Park provides an expansive public space festooned with thought-provoking art installations.

You can come any time to enjoy a picnic and a stroll among the art. You can also buy a ticket for The Looking Glass or attend one of the park’s many free scheduled events. There’s a Saturday farmers market, a Thursday Sunset Market for local crafts and food, the chance to make your own art with free supplies provided Thursdays through Sundays, plus plenty of other chances to explore the world of creativity. 

The Rotunda

Photo credit: rotunda.virginia.edu

As the most striking building on UVA’s beautiful grounds, the Rotunda is well worth your time. Designed by Thomas Jefferson in 1821, the building offers several unique architectural spaces, including the famous and spectacular ‘dome room’. There’s plenty to see when visiting UVA. Just be sure to save time on your Charlottesville bucket list for an exploration of this one-of-a-kind building as it enters its third century as a local and national icon.

Carter Mountain Orchard

We started our list of things to do at Monticello, and we’re ending right next door! Carter Mountain Orchard is open year-round for family fun, and we’re pleased to offer you many special events and activities: seasonal celebrations, summer evenings filled to the brim with good music and wine, and of course the chance to pick your own apples and peaches when they’re in season.

Prefer a more relaxed outing? Just stop in the County Store & Bakery for some ready-picked fruit, Carter Mountain Wine, and bakery treats. You’re always welcome to spread out a blanket and enjoy the best view of Charlottesville. (With a side of our famous apple cider donuts!)


There you have it—our top picks for your Charlottesville bucket list. We’re grateful to be part of a community with so many memorable things to do!

Must-Try Wines from Crozet Wineries

With its fertile soil and temperate climate, Virginia Wine Country is home to dozens of stellar wineries and vineyards. Our Crozet community is particularly special, featuring a stunning array of varietals and a unique setting beneath the Blue Ridge skyline.

To better appreciate our regional bounty, we’re taking a mini tour of Crozet wineries to sample our neighbors’ new, unique, and award-winning wines.

Colonel Richard Tannat at Grace Estate Winery

the colonel wine at grace estate, a crozet winery

Prefer a hearty red wine? Then you’ll love the earthy flavor of the 2019 Colonel Richard Tannat. Grace Estate is one of the few Virginia wineries that grow Tannat grapes, making this wine one to seek out and savor.

Grace Estate joined us on the podium in the 2022 Monticello Wine Cup with their Colonel Richard, as well as the 2018 Le Gras Cuvee and 2018 Gange-Rolv Viognier. Each of these varietals has a distinct flavor profile—you may just need a flight to sample each one!

Plan a day trip to Crozet and savor the sips of Virginia Wine Country! Visit the Monticello Wine Trail website for a map of Crozet wineries.

Cabernet Franc at White Hall Vineyards

2017 cabernet franc from white hall vineyards, a crozet winery

White Hall Vineyards is known for using mature grapes to produce wines with a rich, fruit-forward taste that’s rare among Virginia wineries. Their 2017 Cabernet Franc is no exception, leading with bright notes of sweet cherry and closing with a smooth finish.

Located 13 miles outside Charlottesville, it’s a beautiful spot to escape the hustle of downtown. White Hall is a dog-friendly venue, so bring your furry friend to relax alongside you in the shaded picnic area!

Tavern at Septenary Winery at Seven Oaks Farm

tavern port from septenary winery in crozet

We didn’t have to travel far for a taste of this sweet, port-style dessert wine. Situated on a historic farm in Greenwood, Virginia, Septenary Winery at Seven Oaks Farm is our closest neighbor in the Crozet winery community!

Like other port wines, the Tavern is fortified with brandy. Why? Adding brandy pauses the fermentation at just the right level of sugar (aka sweetness). Its sweet, smooth flavor profile is the perfect fit for holiday sipping by the fireplace.

Crosé at King Family Vineyards

crose at king family vineyards

Just a bit further down the road from Chiswell is King Family Vineyards, another family-owned Crozet winery. Their aptly named Crosé is a crisp, Merlot-based rosé that you can purchase by bottle, glass, or can.

The winery’s sprawling setting often hosts large group gatherings and events. This includes tailgates for Sunday polo matches, which are made particularly convenient by the winery’s cans of Crosé!

Petit Manseng at Chiswell Farm & Winery

2021 petit manseng release at chiswell farm & winery

The 2020 Petit Manseng was among our most popular wines, winning silver in the Monticello Wine Cup alongside our 2020 Cabernet Sauvignon and 2020 Rosé. If you missed the iconic 2020 vintage, have no fear: our 2021 varietal was just released this September!

While Petit Manseng is typically known for its sweetness, ours features an off-dry flavor profile perfectly complemented by notes of lemon, pineapple, and vanilla. Sample this refreshing white from whichever spot you like best: at a dining table on the lawn, in a rocking chair on our covered porch, or in one of our cozy indoor seats.

Craving a glass of wine and have your little ones in tow? Visit the Carter Mountain Wine Shop at our sister venue, Chiles Peach Orchard.


Has our whirlwind tour left you wondering what other experiences there might be in the world of Crozet wineries? Well, the inauguration of our very own Wine Club is just around the corner! Sign up for our Wine Club newsletter for more info about what’s coming up.

Locally-Owned Ice Cream Spots in the Charlottesville Area

Beat the heat with a treat from some of the area’s best ice cream spots. Each of these locally owned and operated institutions serves frozen favorites that make summer that much sweeter.

The Charlottesville and Crozet area is home to mouthwatering options for every meal of the day, including the most important one: dessert!

Chiles Peach Orchard

You didn’t think we’d skip our very own soft serve, did you? Our newly renovated Ice Cream and Wine Shop draws dessert lovers from near and far. The whole family will love our sundaes, milkshakes, and seasonal slushies. Those looking for different treats can savor our cider donuts, homemade pies, fudge, and much more!

Pro tip: Our seasonal slushies (made with orchard-fresh fruit) are the perfect pick for anyone hoping to skip dairy in their dessert!

“The peach ice cream and donuts could save the world.”

Chris W., Google review

Chaps Ice Cream

Chaps Peach Ice Cream
These time-tested flavors are a perfect way to cool off after a hot summer’s day on the Downtown Mall. Photo courtesy of April H. from Yelp.

Located on Charlottesville’s historic Downtown Mall, Chaps Ice Cream is sure to inspire nostalgic memories. The timeless atmosphere isn’t the only thing that can be traced back to the 1950s: all their ice cream is made on-site using a 75-year-old family recipe. From butter pecan to chocolate and sherbet, every flavor is a classic!

If you see peach ice cream on the menu, make sure to try it! This seasonal flavor is made in-house with ripe peaches from Carter Mountain Orchard.

Moo Thru

Lemon sorbet at Moo Thru ice cream in Charlottesville
We love supporting other family farmers! The Smith Family are longtime members of Fauquier County’s dairy farming community.

Originally known to locals as a pullover on Route 29 North near Culpeper, Moo Thru’s Dairy Market location is the newest addition to the Charlottesville ice cream community. This can’t-miss stall scoops ice cream made with all-natural ingredients from a family of Virginia dairy farmers.

It’s nearly impossible to miss Dairy Market’s central location on Preston Avenue. Stop by for the perfect conclusion to a relaxing day at the Washington Park Pool!

Splendora’s Gelato Café

Three scoops of gelato at Splendora's Gelato Cafe
Previously housed in the Downtown Mall, Splendora’s is now located in the Shops at Stonefield Commons.

Splendora’s Gelato Café is a must-visit spot for its unique, handmade gelato. The only venue of its kind in the area, Splendora’s rotates its menu with common and novelty flavors to suit every craving. That’s right, we’re talking everything from chocolate to ghost pepper honey raspberry. If you can’t choose between the old and the new, have no fear! The café’s five-scoop sampler lets you try a little bit of everything.

Plus, Splendora’s new location in the Shops at Stonefield Commons makes it an easy stop for a pick-me-up snack during the day.

Crozet Creamery

Ordering ice cream at Crozet Creamery
With artisanal flavors and dairy-free options, Crozet Creamery has something refreshing for all.

Found in the heart of downtown Crozet in Piedmont Place, Crozet Creamery is a local classic. Each of their flavors, available online in an ever-rotating list of decadent delights, checks all the boxes: handcrafted, taste-tested, and made in small batches every single day.

The creamery’s classic setting is a lovely spot for an impromptu date with that special someone.

La Flor Michoacana

Fruit popsicles at la flor michoacana in Charlottesville
Just one look at these popsicles lets you know they’re made with real fruit.

With the mission to bring the vibrant flavors of Michoacán, Mexico to Charlottesville, La Flor Michoacana is your family’s one-stop shop for all things frozen. Their menu features a broad selection of ice creams, popsicles, and aguas frescas that are homemade with all-natural ingredients. Visitors hoping to stick to the classics are sure to find their favorite flavors, while daring dairy lovers can try flavors like Fruity Pebbles, tamarind chili, or Thai tea!

Chandler’s Ice Cream

This classic soft-serve spot scoops nostalgia in every cone (and milkshake!).

An area favorite, Chandler’s Ice Cream is situated on River Road in Charlottesville. Their short and sweet menu of vanilla, chocolate, and twisted soft serve ice cream (with the classic array of toppings, of course) has a special way of making you feel like a kid again!

Any Chandler’s enthusiast will give you one essential tip before you visit: go hungry! While this spot may be small in appearance, it’s known to pack a serious punch when it comes to serving sizes.

Carter Mountain Orchard

Sanjay Suchak photo of Carter Mountain Orchard ice cream
Ice cream with a view? Yes, please!

It’s impossible to talk about Charlottesville area ice cream without mentioning our sister venue: Carter Mountain Orchard. A short drive from downtown Charlottesville, the orchard is a memorable place to visit for your dessert fix.

All you need to do is walk up to the ice cream window for a delightful soft-serve cone with an unbeatable view. For an added touch of sweetness, enjoy your scoop on top of a pie slice, in a cider donut ice cream sandwich, or in an ice cream slushie float!


Just listing these delicious destinations has our mouths watering and our feet heading for the door. Now, go get yourself some dessert!

Charlottesville Date Ideas for Every Day of the Week

Charlottesville is known for many things: its stunning setting in the Blue Ridge Mountains, a restaurant scene that makes every foodie’s mouth water, and a bustling calendar of activities each week. Among these events are dozens of opportunities for local date nights.

If you’re hoping to do something memorable for your next date night this summer, look no further! Here are a few fun ideas for you and your special someone, right here in Charlottesville.


Monday Walks Along the Rivanna River

Riverview Park | Year ‘Round | 6 AM–9 PM

The Rivanna Trail is a paved pathway starting at Riverview Park and stretching 20 miles around the City of Charlottesville. Everything about this nature trail makes it ideal for a peaceful date night: the trickling sounds of the river, the birds happily chirping above, and especially the way the sun peeks through the trees at sunset.

At Riverview Park and the surrounding trail, visitors are invited to walk, run, bike, fish, or bird watch. No reservations or tickets are required to visit. Plus, The Wool Factory is just around the corner for a post-walk coffee!

Rivanna River walk from Riverview Park

Tuesday Night Trivia

Firefly Restaurant & Game Room | Year ‘Round | 8–10 PM

Think you’re clever? Test your knowledge at Firefly’s trivia night every Tuesday from 8-10 PM! Each week, trivia enthusiasts compete to correctly answer nearly 70 tricky questions for the chance to win a prize. Themes rotate weekly so that brainiacs of all interests have something to contribute. Yes, that means both history buffs and musical geniuses have the chance to succeed!

Trivia is free, although participants are encouraged to make a dinner reservation to guarantee their spot. It’s all fun and games until you plan to join and can’t find a seat for you and your date!

Firefly restaurant trivia sign

Wind Down Wednesdays

Carter Mountain Orchard | June 1–August 31, 2022 | 6–9 PM

As Charlottesville natives, we’re no strangers to the area’s jaw-dropping scenery. In fact, every Wednesday during the summer, we invite visitors up the mountain to unwind with acoustic music and a calming midweek sunset. It’s the perfect way to spend the evening!

Visitors will often enjoy sweet snacks from the Apple Barn (ahem, apple cider donuts), dinner from a local food truck, plus refreshing beverages from the Carter Mountain Wine Shop and Bold Rock Tap Room.

Wind Down Wednesday at Carter Mountain

Tickets are $5 and should be reserved in advance.

Thursday Evening Sunset Series

Carter Mountain Orchard | May 5–September 9, 2022 | 6–9 PM

The fun continues the following night during our Thursday Evening Sunset Series. Each week, visitors join us to dance to their favorite tunes from local performers, all while enjoying the best view of a sunset from anywhere around!

The 2022 season line-up features a rotation of local artists including Jon Spear Band, FarAway, Root Cellar Remedy, The Jackwagons, and many more. To add to the excitement, we’ll also host a rotation of local food trucks—including Vision BBQ, Sweet Jane’s Kitchen, and Good Waffles & Co.—throughout the season.

Tickets are $10 per person. Reserve them in advance because spots fill up quickly!

Thursday evening sunset series at Carter Mountain

Fridays After Five

Ting Pavilion | April 15–September 9, 2022 | 5:30–8:30 PM

If you’re looking for a C’ville tradition to share with your significant other, this is the one! As the name suggests, Fridays After Five is Charlottesville’s weekly concert series that is hosted every Friday…just after five o’clock. Social by nature, this event makes for a unique and low-pressure date night. Half the city is there, after all!

During the summer, community members meet at Ting Pavilion for live music from local performers, craft beverages, and even a few food trucks. Admission is free—just go down to the Downtown Mall to join the fun!

Aerial shot of Ting Pavilion

Looking for a laid-back Friday date? Watch the summer sun descend behind the Blue Ridge Mountains and enjoy live music at Chiswell Farm & Winery’s Summer Sundown in Greenwood!

Saturday Date Night In

Skip the hustle and bustle of downtown Saturday nights by hosting a date night at home! Weekends are the perfect opportunity to pick up a bottle of Carter Mountain Wine and cook up some local food to share in the comfort of home. Maybe even add in a movie to top it all off!

Experience the true taste of the city by picking up dinner ingredients from local vendors that morning at Charlottesville City Market. Of course, we’re there most weeks to satisfy your sweet tooth with plenty of apple cider donuts and homemade fudge for dessert.

Carter Mountain wine lineup

Sunday Salsa

IX Art Park | Year ‘Round | 7–10 PM

Want to try a new out-of-the-box activity? After kicking off in 2001, Sunday Salsa is Virginia’s longest, continually running salsa dance party! It’s a wonderful way for the community to explore dance in a fun, carefree environment.

For those with two left feet, the event starts with a dance lesson by Edwin Roa of Zabor Dance. Once everyone has the chance to get their footing, the party begins! Tickets are $8 per person ($6 for students) and can be reserved online.

Sunday Salsa at IX Art Park

There you have it: a Charlottesville date night for every night of the week! With so many unique local events, there’s always something fun to do. Plus, we’re open daily when you want to kick back and admire the best view around. 

The Best Food in Charlottesville: 10 Iconic Eats You Can’t Miss

Planning a trip to Charlottesville? You’ve probably heard by now that C’ville packs a serious punch when it comes to dining options. From fine dining to cheap eats, the town rivals cities twice its size in the culinary arena.

With world-class restaurants come mouth-watering signature dishes that represent the best of the town. Here’s some of the best food in Charlottesville: iconic fare that you can’t miss while visiting.


Bagels from Bodo’s

Ask anyone from Charlottesville about the best places for a quick bite, and they are sure to mention Bodo’s. Their bagels are a veritable Charlottesville institution and “the number one thing people miss when they move away from Charlottesville” (Real Estate Weekly). This locally-owned bastion of deliciousness has 3 locations with New York-style bagels baked fresh all day, packed with quality meats, veggies, and spreads.

Bodos Egg and Ham Bagle
Photo courtesy of skinnypignyc on Instagram

Ham Biscuit from JM Stock Provisions

Named the “signature dish of Charlottesville“, the ham biscuit is a staple southern fixin’ that can be dressed up or down for any occasion. J.M. Stock Provisions, a local, whole-animal butcher shop has one of the best in town, if you ask us. Just look at that perfectly flaky biscuit and heaping hammy helping.

JR Provision Ham Biscuit
Photo Courtesy of ilovecville on Instagram

Peach Ice Cream from Chaps

Chaps serves premium quality ice cream in a delightful 50s-diner atmosphere, right on Charlottesville’s Downtown Mall. Our flavor of choice? Peach! Using fresh Chiles peaches, the ice cream is a special treat, available only for a limited time during the summer.

Chaps Peach Ice Cream
Photo courtesy of April H. from Yelp

Sandwich with House Dressing from Take It Away

A University of Virginia tradition since 1992, Take It Away serves house-made sandwiches with high-quality ingredients. Their legendary house dressing, made with a secret proprietary recipe, is the perfect spread for any sandwich. Choose your own bread, protein, and embellishments, then layer on the house dressing for added creaminess and that signature flavor.

Take-It-Away Sandwich with House Dressing
Photo Courtesy of takeitawayuva on Instagram

Bronut from Marie Bette

The Brioche Feuilletée, commonly dubbed the Bronut, is a lavish creation by Marie Bette Café and Bakery. Layers of perfectly flaky brioche, butter, sprinkled sugar, and fillings like hazelnut-praline or orange-vanilla form this delectable bakery treat. The Bronut is a can’t-miss C’ville staple and example of European inspiration that adds to our city’s cultural charm.

Bronut from Marie Bette
Photo courtesy of Casey S. from Yelp

Roasted Chicken from Al Carbon

Do you ever get the urge to devour a whole roasted chicken? You don’t have to lie, we’ve been there too. Luckily, Al Carbon is an easy stop off 29 North, especially convenient on the way back to Washington, DC. There you’ll find delicious whole chickens cooked over coals in ovens imported from Peru. The chicken can be enjoyed family-style with sides, or in a giant cemita (Mexican sesame seed bun) piled high with avocado, adobo chipotle peppers, and fresh Oaxacan cheese.

Whole Roast Chicken from Al Carbon
Photo Courtesy of FoodPhotographer from Instagram

Farmer’s Market Tacos

The Farmer’s Market Tacos, aka Maria and Ignacia Mexican Tacos, are a bit more elusive than some of the other dishes on this list. They are served at the Saturday morning IX Art Park Farmer’s Market and at other pop-up locations. C’villians rave about their freshness and authenticity. You’ll want to keep coming back to try all the varieties—chicken, steak, veggie, beef, chorizo, and al pastor.

Mexican Tacos from the Farmers Market
Photo Courtesy of Mexican Tacos Facebook

Kimchi from Sussex Farm

Sussex Farm, also known as The Mama Bird Traditional Korean Cuisine, sells the best kimchi and other Korean staples around. Named Charlottesville’s 2020 Best Food Truck, you can catch them at the IX Art Park Farmer’s Market. Don’t forget to take home some of their beyond free range eggs and homemade BBQ sauces!

Mama Bird Kimchi

Brown’s Fried Chicken

Are we really including fried chicken from a roadside mini-mart among The Best Food in Charlottesville? Yes, yes we are. It’s that good. The regional food blog Roadeats describes Brown’s chicken as “drippy and juicy, fine and fatty, tingling with pepper and a shot of some subtle, sneaky spice that veritably glows on your tongue”. As an added bonus, it’s located along Avon Street heading south out of town, right on the way to Carter Mountain Orchard!

Brown's Assorted Fried Chicken
Photo Courtesy of Javier M. from Yelp

Chiles Family Orchards Cider Donuts

Folks from across the country rave about our apple cider donuts. Made fresh every day, they are melt-in-your-mouth amazing. In addition to the famous apple cider donuts, we also offer strawberry and peach cider varieties in season! Cider donuts are available at both Carter Mountain Orchard and Chiles Peach Orchard.

Chiles Warm Apple Cider Donut

Carter Mountain has one of THE best apple cider donuts we ever had. With a taste of fall in each bite, we most definitely finished the box in a record time!

Ramanoodleseats, Instagram, 10/29/18

There you have it: ten must-eats, the best food in Charlottesville. It was nigh-impossible to narrow down this list—we could have chosen 100 dishes and there would still be some left out. Now if you’ll excuse us, we’re about to go chow down on some apple cider donuts. We worked up quite an appetite going through all of these.

Holiday Gift Guide

Shop local this holiday season with the Chiles Family Orchards holiday gift guide. Browse our Country Store or shop online to find the perfect gift for everyone on your list.

For the Friendly Competitors

Get ready for the ultimate battle of apples versus cider donuts! Duke it out on the solid wood checkerboard featuring Carter Mountain Orchard.

For the Young at Heart

It’s Pin the Tail on the Donkey, winter wonderland style! Stick the Carrot on the Snowman is fun game for all ages and easy to set up anywhere. And how cute is that snowman blindfold?

For the UVA Fan

Cozy up on one of these Kalalou picnic blankets, perfect for cheering on the University of Virginia.

For the Animal Lover

A fun, stylish piece for any children’s room, office, or dorm, these red stags by Cardboard Safari are easy to assemble and lightweight (which makes hanging a breeze). Bonus, the company is based in Charlottesville.

For the Family Hipster

A flattering color for anyone and delightfully warm, our branded beanies are the ideal winter headwear.

For the Fun Uncle

A 2020 collector’s item with a little bit of sass. These masked apple t-shirts are available in adult sizes with short sleeves in blue spruce and long sleeves in crimson.

For the Great British Bake Off Binger

A baking and serving vessel worthy of your home-baked creations! These pie plates are handcrafted in Virginia and oven, microwave, and dishwasher safe.

For the Apple Lover

It’s hard to go wrong with a jar of apple-y goodness. A versatile hostess gift, our Apple Butter and Honeycrisp Apple Sauce are delicious with breakfast, snacks, or dessert. There are so many tasty ways to cook with apple butter.

For the Sandwich Enthusiast

Enjoy our Blackberry Jelly in a classic PB&J or next level variation with honey wheat bread and almond butter. This sweet treat is also delicious with pastries or in thumbprint cookies.

For the Grill Master

Whether you’re firing up the grill for chicken, pulled pork, or ribs, slather on our Peach Barbecue Sauce to add a sweet, tangy flavor.

For the Health Nut

We might be famous for our indulgent apple cider donuts but we love salad too! (We’re farmers, after all.) This sweet, creamy Strawberry Poppyseed Dressing tastes like spring in a bottle and pairs well with spinach.

For the Hard-to-shop Fors

Gift cards are easy-peasy and what we all secretly want anyway.


Ready to knock out your holiday shopping?

Top 10 Things to Do with Kids in Charlottesville

The last five generations of the Chiles family have been born and raised right here in Central Virginia. Throughout the years, we’ve perfected the art of entertaining the whole family! Here are our picks for the best family-friendly activities in Charlottesville. Bonus: most of these businesses are family-owned and operated!

Breakfast and lunch at Bodos Bagels

Dare we say that a trip to Charlottesville wouldn’t be complete without stopping for a New York-style bagel from Bodos Bagels? Locally owned and operated since 1988, Bodos is a Charlottesville institution.

More breakfast and lunch picks:

Dinner and fun with trains at Chew Chew Town

Chew Chew Town is a train-themed restaurant where the Mexican-style food is delivered to your barstool by a choo choo train (get it?). “Junior Conductors” and adults alike will enjoy the delicious food and family-fun atmosphere.

The same Charlottesville family that owns and operates Chew Chew Town serves up Peruvian-style charcoal-roasted chicken, overflowing cemitas, and flavorful tacos right next door at Al Carbon. Offering family-style dinners, Al Carbon has been named one of the best restaurants in Charlottesville by the Charlottesville 29.

More family-friendly dinner picks:

Snacks and Local Products at the Charlottesville City Market

If your family loves fresh veggies, crafts, and a glorious assortment of breakfast and lunch food, the Saturday morning Charlottesville City Market is for you. Kid-friendly favorites include specialty popsicles, colorful flower bouquets, and handmade children’s clothing. The market can get crowded, so plan to get there early for the best selection and stroller-friendly walking.

More specialty shop picks:

Fridays After Five free concert event in Charlottesville
Photo by go4travelblog.com

Live Music at Fridays After Five

Start the weekend off right with live music, family fun, and a rockin’ atmosphere at Fridays After Five, Charlottesville’s free summer concert series. Music performances from local artists and concessions that benefit non-profits create community fun on Charlottesville’s bustling pedestrian Downtown Mall.

More family-friendly live music picks:

Explorative learning at Virginia Discovery Museum

Virginia Discovery Museum believes in exploration through play and focuses on child-centered programs and exhibits. From art projects to STEM labs to Discovery Farms, exhibits engage children cognitively, physically, and socially. Kids learn through play and collaborative problem-solving—and have fun!

Hands-on activities at Thomas Jefferson’s Monticello

Thomas Jefferson’s Monticello is a beautiful World Heritage Site where history comes alive through tours and interactive exhibits. Hands-on spaces such as the Griffin Discovery Room and Mountaintop Hands-on Activity Center engage the whole family. View family-friendly activities at Monticello.

If the kids get antsy during the house tour, there are plenty of grounds to explore—or, pop right next door to Carter Mountain!

More children’s hands-on activity picks:

Kayaking with kids with Rivanna River Company

Kayak trip with Rivanna River Company

Rivanna River Company is a family business that offers guided kayak, canoe, paddleboard, or tubing trips along the scenic Rivanna River (ages 6+). They provide the equipment, shuttle, and guide—you just relax and enjoy the water.

Walking the Saunders-Monticello Trail

Surrounded by 370 acres and traveling through forest, ravines, and mountain views, you don’t want to miss the Saunders-Monticello Trail. A maximum trail grade of 5% makes the trail accessible for the whole family, whether navigating by foot, stroller, or walker. The trail system can be easily accessed near the base of Carter Mountain—come relax after your hike with fresh fruit and cider donuts.

More outdoor recreation picks:

Todd McKinney of Richmond keeps a firm grip on his 2-year-old daughter Madeline as she stands on a ladder to reach for peaches on a tree at Chiles Peach Orchard in Crozet
Photo: Mike Tripp/The News Leader

Fruit Picking at Carter Mountain Orchard

We’re a family farm, so of course, our orchards are kid-friendly. We welcome you to bring the whole family to learn about agriculture, pick delicious fresh fruit, and have fun!

There’s nothing like picking your own sun-ripened peaches and crisp apples straight from the orchard. See what’s in season to pick your own or buy pre-picked on our fruit availability calendar.

If a pick-your-own fruit isn’t in season, pick up a game and a baked good at the Country Store. We recommend bringing home a pie for your next family gathering; our apple pie is a holiday favorite.

Cultivating Curiosity kids event 2018

Country Festivals

From Hop into Spring to July 4th celebrations to the Annual Ol’ Fashioned Peach Festival at our sister orchard, we love a good festival! Orchard festival goers can enjoy games, contests, hayrides, seasonal pickins’ and delicious food.

More festival picks:


Charlottesville is a destination for all sorts of gatherings—weddings, ladies weekends, reunions, romantic couples getaways, and, of course, family vacations. For whatever brings you to town, gather together at Carter Mountain Orchard.

Peak Season Visitor Tips

We are in the thick of apple season! We have thousands of visitors in the month of October, so we’ve assembled some tips to help you navigate your visit whether you’re coming for the first time, or are a seasoned pro. Happy Fall, y’all!

Top Ten Tips for Visiting the Orchard in October

Beat the crowds by coming out during the week or in November

We are open 7 days a week, and weekdays are much less crowded. We offer apple picking, apple cider donuts, apple cider slushies, wine, and hard cider every day, and lunch is served each day except Monday.

Apple picking is typically available ’til mid-November. Get the good ‘uns by checking out our Apple Picking tips video.

Be prepared for all weather and ground conditions

Dress in layers, and have jackets, hats, scarves, and gloves available – it’s often windy. Sunscreen is recommended. To check our weather, use zip code 22902 on your favorite weather app.

Please wear sturdy, close-toed shoes. Boots are recommended if there’s been rain, as parking areas and orchards can get muddy.

There’s no shame in buying pre-picked

Apple picking involves a 5-15 minute hilly walk in each direction. We have plenty of already-picked apples if you don’t wish to pick your own.

Weekend and holiday traffic and parking information:
  1. Please arrive as early as possible (Hours of Operation) to be assured of parking. Keep in mind that apple picking ends one hour prior to closing.
  2. We contract with a professional parking and traffic control service. Please follow all directions from these attendants
  3. Be prepared for slow-moving traffic both entering and departing the orchard during peak times.
  4. Our only entrance and exit is located on Route 53 (Thomas Jefferson Parkway), a winding 2-lane road which we share with Monticello, Michie Tavern, Highland, area wineries, and local residents. October is peak season and traffic is often heavy on area roads. We have a flagman moving traffic, and we work closely with our local police department.  Many of you are making a left turn when you leave the orchard. When there are a lot of cars departing at one time, it will take time to get everyone safely down the mountain and merged into the traffic flow on Route 53. We appreciate your patience and understanding that we have no control over local traffic and other events, nor how many folks visit us at any given time.
  5. On occasion, we reach full capacity in our parking lots. There is no off-site parking. If we reach that capacity, we have to deny access to our entrance until parking spaces clear out.
  6. Follow us on Twitter for regular parking and traffic updates as you are approaching Charlottesville so you will be fully informed.
  7. Vehicles over 20 feet, unfortunately, cannot be accommodated on the weekends, as there is no parking and turnaround space. Weekday parking is not an issue.
Sorry, no dogs allowed

Update 07.22.2020: We have made the difficult decision to no longer allow dogs or other pets on our property. There are several reasons for this policy change, and we thank you for your understanding. 

Are you a Leaf Peeper?

Virginia fall foliage typically peaks in late October or early November. 2018 has been an extremely wet year and our foliage is expected to turn color later than normal.

For more information, please review our Visitor GuidelinesHave a wonderful time and thank you for supporting our family farm!

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