Wineries with live music in Loudoun County
23 of the 43 wineries in Loudoun County host live music, according to their own websites. Each entry quotes the winery's policy and links to where it came from. Last checked October 31, 2026.
Coming up
- Sun, Nov 1Live Music with Gary Smallwood8 Chains North Winery, Waterford
- Sun, Nov 1Scott KurtFleetwood Farm Winery, Leesburg
- Sun, Nov 1Live Music: Jason MasiDoukenie Winery, Hillsboro
- Sun, Nov 1Ken WenzelBreaux Vineyards, Purcellville
- Sun, Nov 1Lucas MasonOld Farm Winery at Hartland, Aldie
- Sat, Nov 7Live Music with The Train Wreck EndingsCasanel Vineyards & Winery, Leesburg
- Sat, Nov 7Live Music with Brian Franke8 Chains North Winery, Waterford
- Sat, Nov 7Garrett MabeFleetwood Farm Winery, Leesburg
- Sat, Nov 7Live Music: Stanley WhitakerDoukenie Winery, Hillsboro
- Sat, Nov 7Melissa Quinn Fox 2Breaux Vineyards, Purcellville
- Sat, Nov 7Rich SheeheOld Farm Winery at Hartland, Aldie
- Sat, Nov 7Live Music with Rocco & Friends on Nov 7Good Spirit Farm Winery, Round Hill
Live music most weekends
8 Chains North Winery
Waterford, Loudoun County
The calendar lists live music most Saturdays and Sundays from 1:30 to 4:30 pm.
From their “calendar” page, checked October 31, 2026
868 Estate Vineyards
Hillsboro, Loudoun County
Live music is scheduled on weekends from May through October, plus festivals and summer concerts.
From their “music at 868” page, checked October 31, 2026
Bleu Frog Vineyards
Leesburg, Loudoun County
Live music is held Saturdays and Sundays from 1:30 to 4:30 pm.
From their home page, checked October 31, 2026
Bluemont Vineyard
Bluemont, Loudoun County
Sunset Saturdays bring live music to the 951 Tasting Room patio on Saturday afternoons and evenings, mainly spring through fall.
From their “vendors live music” page, checked October 31, 2026
Bozzo Family Vineyards
Purcellville, Loudoun County
The live music program runs from April to mid-November.
From their “news events” page, checked October 31, 2026
Breaux Vineyards
Purcellville, Loudoun County
Live music is scheduled most Saturdays and Sundays from 2 to 5 PM.
From their “events” page, checked October 31, 2026
Casanel Vineyards & Winery
Leesburg, Loudoun County
Live music is scheduled on most Saturday afternoons (e.g., Nov 7, 21 and 28, 2026).
From their “upcoming events” page, checked October 31, 2026
Creek's Edge Winery
Lovettsville, Loudoun County
Live music is held most Saturdays and Sundays in the afternoon, roughly 1–5pm.
From their “events” page, checked October 31, 2026
Doukenie Winery
Hillsboro, Loudoun County
Local Rock, Pop, and Folk musicians perform on Saturdays and Sundays.
From their “visit us” page, checked October 31, 2026
Fleetwood Farm Winery
Leesburg, Loudoun County
There is typically live music every weekend, plus trivia night every other Friday.
From their “faq” page, checked October 31, 2026
Good Spirit Farm Winery
Round Hill, Loudoun County
Live music is held on many Saturdays from 2-5 PM, for example Nov 7, Nov 14, Dec 12 and Dec 19, 2026.
From their “ourevents” page, checked October 31, 2026
Notaviva Winery
Hillsboro, Loudoun County
Friday-night Bluegrass Jams run 5-9 on scheduled dates (11/6, 11/20, 11/27, 12/4, 12/18).
From their home page, checked October 31, 2026
October One Vineyard
Leesburg, Loudoun County
Live music is on the First Friday of each month, 5 pm - 9 pm.
From their “events” page, checked October 31, 2026
Old Farm Winery at Hartland
Aldie, Loudoun County
Live music is scheduled most Saturdays and Sundays from 2:00 PM to 6:00 PM.
From their “calendar” page, checked October 31, 2026
Quattro Goombas Winery
Aldie, Loudoun County
Live music in the brewery on Fridays 5-8pm and Saturdays 2-5pm.
From their home page, checked October 31, 2026
The Barns at Hamilton Station
Hamilton, Loudoun County
Live music is held every Saturday and Sunday from 2:00 to 5:00pm, rain or shine, moving indoors in bad weather.
From their “reopening info” page, checked October 31, 2026
Three Creeks Winery
Hamilton, Loudoun County
Live music is scheduled on about two Fridays a month from 4:00pm to 7:00pm, plus occasional other dates.
From their “music” page, checked October 31, 2026
Two Twisted Posts Winery
Purcellville, Loudoun County
Live music every weekend, plus late-night music 5-8pm on 3rd Fridays and karaoke 2-5pm on 1st Sundays.
From their home page, checked October 31, 2026
Live music some days
Carriage House Wineworks
Waterford, Loudoun County
Live music is offered at some events, such as Taste of Rosé Weekend and Mother's Day.
From their “events” page, checked October 31, 2026
Firefly Cellars
Hamilton, Loudoun County
Live music is offered on select weekend days; check the calendar for details.
From their “visit” page, checked October 31, 2026
Hidden Brook Winery
Leesburg, Loudoun County
The events page links to a live music schedule, but no frequency is given.
From their “events” page, checked October 31, 2026
Mount Defiance Cidery
Middleburg, Loudoun County
Live music is scheduled at some events, often on Saturdays from 1pm to 4pm.
From their “all events” page, checked October 31, 2026
Sunset Hills Vineyard
Loudoun County
The site mentions live music but publishes no schedule.
From their “Home” page, checked October 31, 2026
Common questions
- Which wineries in Loudoun County have live music?
23 of the 43 wineries we track in Loudoun County host live music: 8 Chains North Winery, 868 Estate Vineyards, Bleu Frog Vineyards, Bluemont Vineyard, Bozzo Family Vineyards, Breaux Vineyards, Carriage House Wineworks, Casanel Vineyards & Winery, Creek's Edge Winery, Doukenie Winery, Firefly Cellars, Fleetwood Farm Winery and 11 more. Each answer comes from the winery’s own website.
- What are the rules at wineries with live music in Loudoun County?
Policies differ: 18 live music most weekends, 5 live music some days. Check each winery’s page for the details and exceptions.
More guides: dog-friendly wineries, kid-friendly wineries, wineries for a picnic, adults-only wineries, wineries for groups and limos, wineries with food, wineries that take walk-ins.