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 at a hidden gem, there’s always someone playing something in C’ville. In fact, each of our venues — Carter Mountain Orchard, Chiles Peach Orchard, and Chiswell Farm & Winery — has live music events throughout the year.
There are so many opportunities to see live music acts all around this area any day of the week. The Visit Charlottesville website has a Concerts & Live Music page which keeps track of new and exciting events and acts coming to town. 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
Enjoying area bands and unbeatable views at Carter Mountain Orchard’s weekly Thursday Evening Sunset Series is a Charlottesville tradition. Locals and tourists alike come up from April ’til October for golden hour concerts high above the city. Grab a spot at a table, spread out a blanket, or simply dance the dusk away, it’ll be a good time!
There’s different bands every week, playing rock, blues, country, bluegrass, and more. You’ll find a variety of delicious food trucks from all over town, refreshing Carter Mountain Wine, and hard cider at the Bold Rock Taproom. And of course, it’s simply 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 to make it a weekly habit.
In addition to the Sunset Series, Carter Mountain also hosts live music acts during special occasions and festivities. Check our events calendar to see what’s coming up, from spring’s Easter Eggstravaganza and summer’s Peach Jam-Boree to the festive Thursday Evening Holiday Series in December.
The Downtown Mall
The pedestrian mall is our city’s signature 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 Baby Jo’s Boogie Band on Mondays. The Bebedero regularly features live samba, rumba, and Latin guitar, 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 vibe. And if you’re a fan of orchestral music or eclectic touring artists, it’s worth looking through The Paramount’s events calendar from time to time.
Lots of restaurants and bars have one-off or impromptu performances, so if you have the time, it’s worth taking a stroll and seeing what’s playing — you’re likely to run into street musicians and outdoor artists without even trying! For a more detailed list of smaller performances, check the Cville Scene.
The Ting Pavilion
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.
Local Wineries
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. There are acoustic musicians on Friday evenings and Sunday afternoons at the historic Jefferson Vineyards. And Keswick Vineyards features live music every Saturday, as well as at their “Wine Down Wednesday” series.
We own and operate Chiswell Farm & Winery near Crozet, which hosts Summer Sundown, a free concert series during the warmer months. You’ll also find live music at special events and monthly Music Trivia Nights. If you’re coming to a Chiswell performance, we recommend packing a picnic to go with your wine!
Summer Sundown
First Fridays, May–Oct.
Enjoy an evening of acoustic performers, food vendors, and incredible wine out on a picturesque lawn. Nestled in the foothills of the Blue Ridge, Chiswell Farm & Winery features a historic estate and panoramic views of the countryside. Learn more
University of Virginia and PVCC Concerts
Every school year, Charlottesville’s population swells with UVA’s students and faculty, and there’s a surprising number of world-class musicians among them! UVA’s Department of Music features over a hundred concerts every year from dozens of local and visiting ensembles. While touring the University’s gorgeous Grounds with visiting relatives, these concerts are easy ways to treat them to a little live music in Charlottesville, as well. 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. Both schools have more traditional sit-down music venues for quieter performances. Combined with beautiful outdoor spaces and convenient locations, they’re relaxing places to spend an evening with friends and family.
Crozet Breweries and Orchards
Grown from a rural farming community, the small town of Crozet is a unique cultural destination just west of Charlottesville. The famous breweries, wineries, 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. Our venue, Chiles Peach Orchard, is just down the road from downtown Crozet. We host free live performances every Saturday and Sunday for most of the year on its outdoor stage. There are also regular weekend events, like Fall Into Fun or Homemade Peach Ice Cream Days, so look at the Chiles calendar to see what’s happening!
Live Music Weekends
Saturdays & Sundays, May–Nov.
Throughout fruit and flower picking seasons, Chiles Peach Orchard has live tunes each weekend afternoon. From 1–4 PM on Saturdays and Sundays, performers play on the outdoor stage. So grab a snack, drink, or ice cream cone from the Clubhouse and relax to the orchard rhythms! Learn more
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, so you can grab a snack, play an outdoor game, or even pick your own fruit before, during, and 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! Make a plan to see some live music this week by checking out our calendars. There are all sorts of events being planned at our Chiles Family Orchards venues that are sure to get your feet tapping. We hope to see you soon!
