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

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

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

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

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

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

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!

The Chiles family has been farming in Central Virginia for over 100 years—you could say that we know a thing or two about what to do in Charlottesville, Virginia. Read on for our inside guide on to how to spend the perfect ladies weekend in Charlottesville. Leave the kids and hubby at home—Momma needs some time with her girlfriends!

Friday Night: Out on the Town

From cute boutiques to entertainment venues, the Downtown Mall has it all.

Indulge in Retail Therapy

First stop: Charlottesville’s downtown pedestrian mall. Sneak in some retail therapy at the mall’s charming boutiques stocked full of gifts, accessories, and decor that you might not need but will absolutely want. We love Roxie Daisy for home décor, O’Suzannah for candles, lotions, books, and other odds n ends, and Rock Paper Scissors for the cutest stationary you’ve ever seen.

Relax with Dinner and a (Free!) Show

Anyone can appreciate the price of the next stop: free. Soak in the sun while getting your groove on at Fridays after Five, a free concert series on Charlottesville’s downtown pedestrian mall that takes place, you guessed it, every Friday after 5 PM.

For music lovers looking to start their “Cville” weekend early, visit the mountain for the Thursday Evening Sunset Series, a free event featuring live music, dinner, and wine and hard cider tastings.

After the concert, dinner on the mall is a must. For an upscale vibe with fancy food and fantastic views, opt for Commonwealth Sky Bar. If the ladies love sushi, there’s nowhere better than Ten. Looking for something more casual? Venture off the tourist path with margaritas and Texas-style tacos at Brazos Tacos in the industrial IX Art Park, located a few blocks from the downtown mall.

Saturday: Eat, Drink, Repeat

Fresh veggies are a favorite find at the Charlottesville City Market. Instagram: @CvilleCityMarkets

Start the Morning Bright and Early at the Charlottesville City Market.

It may be 8 AM but it’s never too early for tacos, especially not the authentic Mexican tacos the Charlottesville City Market dishes out. Farmer’s market purists will appreciate the locally-roasted coffee, locally-raised meats, and locally-grown flowers (sensing a theme?). But don’t fill up too early—the tastiest part of the day is still to come.

C’mon Up to Carter Mountain

Drive up the mountain for pick-your-own seasonal fruit (see our fruit availability calendar for details). Come early to beat the crowds and don’t forget your camera—the best view in town and rows of fruit trees are highly Instagram-able. After you’ve picked your fill, visit the Country Store for fresh cider donuts, sugar coma-inducing desserts, and apple cider. Claim a picnic table for the group, spread out the goodies, and dig in.

Wine lovers don’t have to go far to taste Virginia’s favorite libation; Prince Michel Vineyard and Winery has a tasting room right here on Carter Mountain. Prince Michel has been using Carter Mountain grapes to create their award-winning wines for years—talk about #drinklocal! Hard cider fans can enjoy a flight, pint, or growler of cider, fresh from the tap at Bold Rock Hard Cider Cellar.

Explore Charlottesville’s many wineries or stay up on the mountain for sweet views with your booze.

Wine and Dine

If Central Virginia had a middle name, it’d be “Incredible Wineries.” For a winery map and guide, check out the Monticello Wine Trail. Some highlights include Jefferson Vineyards, Blenheim Vineyards, and Pippin Hill—all within a 20-minute drive from the orchard. In all our years, we’ve never grown tired of the booze and views Cville offers.

If you’re not completely stuffed by the end of the day, venture into quaint downtown Belmont for dinner. The cluster of restaurants hidden within one of the city’s oldest neighborhoods lay claim to some of the best eats in town. Go family-style with sangria and tapas at Mas (consistently voted best restaurant in Cville), share an intimate rustic Italian dinner at Tavola, or go local with Virginia eats at The Local.

Sunday Morning: Walk it Off

UVA’s historic Rotunda

Get Outside for Fresh Air and Exercise

Grab a latte from local favorite Shenandoah Joe’s coffee roasters and then take an early-morning stroll through UVA’s grounds. Enjoy the Jeffersonian architecture and channel your inner founding father (no judgment if you feel the urge to break into a Hamilton number). If your hiking boots are burning a hole in your knapsack, trek out to Monticello Trail—bonus, it’s only minutes from Carter Mountain, making it easy to pop up for a Sunday morning donut and extra cider to bring home.

Brunch ‘til You Drop

Then, if there’s still room after Saturday, it’s time for what is arguably the most important component of a ladies’ weekend: brunch. In our biased opinion, the all-you-can-eat pancake breakfast at our sister orchard Chiles Peach Orchard in nearby Crozet is the best brunch option. Pancakes piled high with seasonal fruit topping is the ultimate comfort food, and when you pair them with a fresh breeze and view of the fruit trees in the valley, it’ll be hard to head home and leave ladies weekend behind.