Events & happenings

One calendar for what's on in Loudoun wine country — live music, seasonal festivals, dinners, and events at the wineries and breweries, plus the signature town celebrations — gathered in one place and refreshed every week.

This is a partial listing of what's going on in the area — curated across places we like, bands we know, and things that just look interesting. It's refreshed weekly and since details can change, we encourage you to check the venue's own site for final confirmation before heading out.

October–November 2026

Autumn wine dinners and regional tastings

Several special wine-and-food programs fall between mid-October and late November, including paired dinners, an awards tasting and a collaborative producer event.

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All upcoming dates · Virginia time · As of Wed, Oct 28, 2026

167 published events · 197 scheduled listings

Each event counts once in the current filters. Selected dates have separate listings; a daily date range appears once. Private drafts and hidden events are excluded.

October 202612 listings

Wed, Oct 28, 2026

Fri, Oct 30, 2026

Sat, Oct 31, 2026

November 202669 listings

Sun, Nov 1, 2026

Fri, Nov 6, 2026

Sat, Nov 7, 2026

Sun, Nov 8, 2026

Thu, Nov 12, 2026

Fri, Nov 13, 2026

Sat, Nov 14, 2026

Sun, Nov 15, 2026

Fri, Nov 20, 2026

Sat, Nov 21, 2026

Sun, Nov 22, 2026

Wed, Nov 25, 2026

Fri, Nov 27, 2026

Sat, Nov 28, 2026

Sun, Nov 29, 2026

December 202697 listings

Thu, Dec 3, 2026

Fri, Dec 4, 2026

Sat, Dec 5, 2026

Sun, Dec 6, 2026

Thu, Dec 10, 2026

Fri, Dec 11, 2026

Sat, Dec 12, 2026

Sun, Dec 13, 2026

Thu, Dec 17, 2026

Fri, Dec 18, 2026

Sat, Dec 19, 2026

Sun, Dec 20, 2026

Mon, Dec 21, 2026

Tue, Dec 22, 2026

Wed, Dec 23, 2026

Thu, Dec 24, 2026

Sat, Dec 26, 2026

Sun, Dec 27, 2026

Thu, Dec 31, 2026

January 202719 listings

Sat, Jan 2, 2027

Sun, Jan 3, 2027

Fri, Jan 8, 2027

Sat, Jan 9, 2027

Sun, Jan 10, 2027

Fri, Jan 15, 2027

Sat, Jan 16, 2027

Sun, Jan 17, 2027

Thu, Jan 21, 2027

Keep exploring

Visit Loudoun events ↗Get Out Loudoun calendar ↗

Schedules and availability can change; see the organizer’s listing for current details.

Upcoming Events

Autumn wine dinners and regional tastings

October 202612 listings

Oct28WedHalloween Themed Bingo & BrewBear Chase Brewing Company · BluemontWed, Oct 28, 20266:30 pm–8:30 pmHolidaysOther eventsDetails

Oct30FriLucas MasonBluemont Station Brewery & Winery · BluemontFri, Oct 30, 20265 pm–8 pmLive musicDetails

Oct30FriLive Music featuring Steve OneshoesLost Barrel Brewing · MiddleburgFri, Oct 30, 20265:30 pm–8:30 pmLive musicDetails

Oct30FriLaura Cashman — Acoustic Live MusicHarvest Gap Brewery · HillsboroFri, Oct 30, 20266 pm–9 pmLive musicDetails

Oct31SatLive Music Series – Curt CunninghamCana Vineyards · MiddleburgSat, Oct 31, 202612 pm–4 pmLive musicDetails

Oct31SatJoel DelgadoBluemont Station Brewery & Winery · BluemontSat, Oct 31, 20261 pm–4:30 pmLive musicDetails

Oct31SatLive Music: Bearded HarmonyDelaplane Cellars · DelaplaneSat, Oct 31, 20261 pm–5 pmLive musicDetails

Oct31SatLive Music Featuring Juliet LloydLost Barrel Brewing · MiddleburgSat, Oct 31, 20264 pm–7 pmLive musicDetails

Oct31SatRich SheeheBluemont Station Brewery & Winery · BluemontSat, Oct 31, 20265 pm–8 pmLive musicDetails

Oct31SatFearFest – A Night with Edgar Allan PoeSlater Run Vineyards · UppervilleSat, Oct 31, 20266 pm–10 pmArts & cultureHolidaysDetails

Oct31SatHalloween Beer DinnerDirt Farm Brewing · BluemontSat, Oct 31, 20266 pm–8 pmFood & pairingsHolidaysDetails

Oct31SatMonster Mash: A Halloween Dance PartySlater Run Vineyards · UppervilleSat, Oct 31, 20268 pm–10 pmLive musicHolidaysDetails

November 202669 listings

Nov1SunLive Music: Mo & Mary MacDelaplane Cellars · DelaplaneSun, Nov 1, 20261 pm–5 pmLive musicDetails

Nov1SunJosh SowderBluemont Station Brewery & Winery · BluemontSun, Nov 1, 20262 pm–5 pmLive musicDetails

Nov1SunKen WenzelBreaux Vineyards · PurcellvilleSun, Nov 1, 20262 pm–5 pmLive musicDetails

Nov1SunHONKYTONK Night – Free Line DancingLost Barrel Brewing · MiddleburgSun, Nov 1, 20264 pm–7 pmOther eventsDetails

Nov6FriPurcellville Artisan Tour- Purcellville VA 20132 · PurcellvilleFri, Nov 6, 2026Time not yet confirmedArts & cultureDetails

Nov7SatPurcellville Artisan TourTown of Purcellville · PurcellvilleSat, Nov 7, 2026 – Sun, Nov 8, 2026 · Daily11 am–5 pm dailyArts & cultureMarkets & fairsDetails

Nov7SatLive Music: The Cold NorthDelaplane Cellars · DelaplaneSat, Nov 7, 20261 pm–5 pmLive musicDetails

Nov7SatFocaccia Making ClassBreaux Vineyards · PurcellvilleSat, Nov 7, 20262 pm–4 pmClasses & workshopsFood & pairingsDetails

Nov7SatLive Music: Stanley WhitakerDoukénie Winery · HillsboroSat, Nov 7, 20262 pm–5 pmLive musicDetails

Nov7SatMelissa Quinn FoxBreaux Vineyards · PurcellvilleSat, Nov 7, 20262 pm–5 pmLive musicDetails

Nov7SatHarvest Party at Bluemont VineyardBluemont Vineyard · BluemontSat, Nov 7, 20266–8 p.m.; optional cellar tour at 5 p.m.Festivals & celebrationsWine tastingsDetails

Nov7SatPictrola at Lost RhinoLost Rhino Brewing Co. · AshburnSat, Nov 7, 20266 pmLive musicDetails

Nov7SatPost Harvest Wine DinnerDoukénie Winery · HillsboroSat, Nov 7, 20266:30 pm–9 pmFood & pairingsDetails

Nov8SunSip & Focaccia Art Workshop with Merrick Mama BakesDirt Farm Brewing · BluemontSun, Nov 8, 202611 am–1 pmClasses & workshopsFood & pairingsDetails

Nov8SunLive Music: Laura CashmenDelaplane Cellars · DelaplaneSun, Nov 8, 20261 pm–5 pmLive musicDetails

Nov8SunLive Music: The Cold NorthDoukénie Winery · HillsboroSun, Nov 8, 20262 pm–5 pmLive musicDetails

Nov12ThuThe Spanish Table: A Tapas & Wine ExperienceEchelon Wine Bar · LeesburgThu, Nov 12, 20265 pm–7:45 pmFood & pairingsDetails

Nov13FriChick’s Picks Holiday Pop-UpVanish Farmwoods Brewery · LuckettsFri, Nov 13, 20269 am–7 pmMarkets & fairsHolidaysDetails

Nov13FriHarvest DinnerStone Tower Winery · LeesburgFri, Nov 13, 20266:30 pmFood & pairingsDetails

Nov13FriNovember Family DinnerWilliams Gap Vineyard · Round HillFri, Nov 13, 20266:30–8:30 pm; confirm current details with the organizerFood & pairingsWine tastingsDetails

Nov14SatLive Music Series – David DavolCana Vineyards · MiddleburgSat, Nov 14, 20266 am–1 pmLive musicDetails

Nov14SatAnnual Crafts & CheerCana Vineyards · MiddleburgSat, Nov 14, 202611 am–6 pmMarkets & fairsHolidaysDetails

Nov14SatEasy as Pie Wine PairingBoxwood Estate Winery · MiddleburgSat, Nov 14, 202612 pm–2 pmWine tastingsFood & pairingsDetails

Nov14SatLoCo CiderFestGreat Country Farms / Henway Hard CiderSat, Nov 14, 202612 pm–5 pmFestivals & celebrationsDetails

Nov14SatLive Music: Meisha HerronDelaplane Cellars · DelaplaneSat, Nov 14, 20261 pm–5 pmLive musicDetails

Nov14SatLaura CashmanBreaux Vineyards · PurcellvilleSat, Nov 14, 20262 pm–5 pmLive musicDetails

Nov14SatLive Music: Gary SmallwoodDoukénie Winery · HillsboroSat, Nov 14, 20262 pm–5 pmLive musicDetails

Nov14SatMelissa Quinn Fox Duo — Acoustic Country & AmericanaHarvest Gap Brewery · HillsboroSat, Nov 14, 20262 pmLive musicDetails

Nov14SatLoudoun Pours to Explore — Sauvignon Blanc & Cabernet FrancBluemont Vineyard · BluemontSat, Nov 14, 20266 pm–8 pmWine tastingsClasses & workshops+2 moreDetails

Nov14SatSOMMinar – Single-Varietal RedsStone Tower Winery · LeesburgSat, Nov 14, 2026 · Selected dates11 am and 2:30 pm on each listed dateClasses & workshopsDetails

Nov15SunLive Music: Opposite ShoresDelaplane Cellars · DelaplaneSun, Nov 15, 20261 pm–5 pmLive musicDetails

Nov15SunJessica Paulin — Live MusicHarvest Gap Brewery · HillsboroSun, Nov 15, 20262 pm–5 pmLive musicDetails

Nov15SunLive Music: Joey & The WaitressDoukénie Winery · HillsboroSun, Nov 15, 20262 pm–5 pmLive musicDetails

Nov15SunSOMMinar – Single-Varietal RedsStone Tower Winery · LeesburgSun, Nov 15, 2026 · Selected dates11 am and 2:30 pm on each listed dateClasses & workshopsDetails

Nov20FriNovember Comedy Night at BreauxBreaux Vineyards · PurcellvilleFri, Nov 20, 20267 pm show; doors open at 6 pmArts & cultureDetails

Nov20FriFriends with BenefitsWalsh Family Wine · PurcellvilleFri, Nov 20, 2026Time not yet confirmedWine tastingsDetails

Nov21SatLoCo Wine FestivalOld Farm WinerySat, Nov 21, 2026 – Sun, Nov 22, 2026 · DailyNoon–5 p.m. dailyFestivals & celebrationsDetails

Nov21SatThe Pit Jumper Barrel Tasting & VerticalSlater Run Vineyards · UppervilleSat, Nov 21, 202612 pm–1 pmWine tastingsDetails

Nov21SatLive Music: Shane GambleDelaplane Cellars · DelaplaneSat, Nov 21, 20261 pm–8 pmLive musicDetails

Nov21SatLive Music: Bearded HarmonyDoukénie Winery · HillsboroSat, Nov 21, 20262 pm–5 pmLive musicDetails

Nov21SatMelanie PearlBreaux Vineyards · PurcellvilleSat, Nov 21, 20262 pm–5 pmLive musicDetails

Nov21SatSip & Savor Series: New World Wines & BitesEchelon Wine Bar · LeesburgSat, Nov 21, 20262 pm–5 pmFood & pairingsDetails

Nov21SatMagic on the MountainWalsh Family Wine · PurcellvilleSat, Nov 21, 20266:30 pm–9:30 pmWine tastingsFood & pairingsDetails

Nov21SatFreeze Your Gizzard 5K Cross Country Race and 1-Mile Fun RunFestival Field · LeesburgSat, Nov 21, 20265K at 9:00 am; one-mile run at 10:00 amOutdoors & wellnessDetails

Nov21SatSOMMinar – Single-Varietal RedsStone Tower Winery · LeesburgSat, Nov 21, 2026 · Selected dates11 am and 2:30 pm on each listed dateClasses & workshopsDetails

Nov22SunDog DaysDelaplane Cellars · DelaplaneSun, Nov 22, 202611 am–6 pmOther eventsDetails

Nov22SunLive Music: Gary SmallwoodDelaplane Cellars · DelaplaneSun, Nov 22, 20261 pm–5 pmLive musicDetails

Nov22SunThanksgiving, UncorkedWilliams Gap Vineyard · Round HillSun, Nov 22, 20261:00 pm; end time unconfirmedHolidaysDetails

Nov22SunLevi StephensBreaux Vineyards · PurcellvilleSun, Nov 22, 20262 pm–5 pmLive musicDetails

Nov22SunLive Music: Sarah CooperDoukénie Winery · HillsboroSun, Nov 22, 20262 pm–5 pmLive musicDetails

Nov22SunSOMMinar – Single-Varietal RedsStone Tower Winery · LeesburgSun, Nov 22, 2026 · Selected dates11 am and 2:30 pm on each listed dateClasses & workshopsDetails

Nov25WedEighth Annual Pre-Turkey Hill ClimbDirt Farm Brewing · BluemontWed, Nov 25, 20269 am–5 pmOutdoors & wellnessDetails

Nov25WedTurkey TrekStone Tower Winery · LeesburgWed, Nov 25, 202611 am–2:30 pmOutdoors & wellnessHolidays+1 moreDetails

Nov27FriVines & Views HikeBreaux Vineyards · PurcellvilleFri, Nov 27, 2026 · Selected dates11 am; approximately one hourWine tastingsOutdoors & wellnessDetails

Nov27FriMoe StringzBear Chase Brewing Company · BluemontFri, Nov 27, 20261 pm–5 pmLive musicDetails

Nov27FriGrayson MoonBreaux Vineyards · PurcellvilleFri, Nov 27, 20262 pm–5 pmLive musicDetails

Nov27FriLighting of the Vines: Launch Party WeekendBluemont VineyardFri, Nov 27, 2026 – Sat, Nov 28, 2026 · DailyProgram 4–7 p.m. each evening; illumination at 5:30 p.m.Festivals & celebrationsHolidaysDetails

Nov27FriNovember Club Night — A Jingle Jangle PartyWalsh Family Wine · PurcellvilleFri, Nov 27, 2026Time not yet confirmedHolidaysOther eventsDetails

Nov28SatDirt Farm Christmas Market — SaturdayDirt Farm Brewing · BluemontSat, Nov 28, 202611 am–4 pmMarkets & fairsHolidaysDetails

Nov28SatLive Music: The Cold NorthDelaplane Cellars · DelaplaneSat, Nov 28, 20261 pm–5 pmLive musicDetails

Nov28SatLive Music: Shane GambleDoukénie Winery · HillsboroSat, Nov 28, 20262 pm–5 pmLive musicDetails

Nov28SatScott Kurt — Live MusicBreaux Vineyards · PurcellvilleSat, Nov 28, 20262 pm–5 pmLive musicDetails

Nov28SatDelta Spur DuoBear Chase Brewing Company · BluemontSat, Nov 28, 20266 pm–9 pmLive musicDetails

Nov28SatPictrola at Monk's BBQMonk’s BBQ · PurcellvilleSat, Nov 28, 20267 pmLive musicDetails