Events & happenings

Live music, tastings and local events. Confirm details with the venue.

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146 events · 180 scheduled listings

October 202645 listings

Thu, Oct 15, 2026

Fri, Oct 16, 2026

Sat, Oct 17, 2026

Sun, Oct 18, 2026

Thu, Oct 22, 2026

Fri, Oct 23, 2026

Sat, Oct 24, 2026

Sun, Oct 25, 2026

Mon, Oct 26, 2026

Wed, Oct 28, 2026

Fri, Oct 30, 2026

Sat, Oct 31, 2026

November 202650 listings

Sun, Nov 1, 2026

Sat, Nov 7, 2026

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Thu, Nov 12, 2026

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Sat, Nov 14, 2026

Sun, Nov 15, 2026

Fri, Nov 20, 2026

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Sun, Nov 29, 2026

December 202678 listings

Thu, Dec 3, 2026

Fri, Dec 4, 2026

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Sun, Dec 6, 2026

Thu, Dec 10, 2026

Fri, Dec 11, 2026

Sat, Dec 12, 2026

Sun, Dec 13, 2026

Thu, Dec 17, 2026

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Tue, Dec 22, 2026

Wed, Dec 23, 2026

Thu, Dec 24, 2026

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Sun, Dec 27, 2026

Thu, Dec 31, 2026

January 20277 listings

Sat, Jan 2, 2027

Sun, Jan 3, 2027

Fri, Jan 8, 2027

Sat, Jan 9, 2027

Sun, Jan 10, 2027

Thu, Jan 21, 2027

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Visit Loudoun events ↗Get Out Loudoun calendar ↗

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

Upcoming Events

October 202645 listings

Oct15ThuFriends & Flannel: Ladies Night Out868 Estate VineyardsThu, Oct 15, 20265 pm–9 pmOther eventsDetails

Oct15ThuCelebrate PurcellvilleTown of Purcellville · PurcellvilleSat, Oct 10, 2026 – Sat, Oct 17, 2026 · DailyActivities daily; times vary. Finale October 17, 2–5 pm.Festivals & celebrationsDetails

Oct15ThuMiddleburg Film FestivalMiddleburg Film Festival · MiddleburgThu, Oct 15, 2026 – Sun, Oct 18, 2026 · DailyScreenings daily; times vary by film and venue.Festivals & celebrationsArts & cultureDetails

Oct16FriChuck DardenBluemont Station Brewery & Winery · BluemontFri, Oct 16, 20265 pm–8 pmLive musicDetails

Oct16FriTerroir to Table: Harvest Wine DinnerEchelon Wine Bar · LeesburgFri, Oct 16, 20266:30 pm–9 pmFood & pairingsDetails

Oct17Sat6th Annual Beer FestivalBear Chase Brewing Company · BluemontSat, Oct 17, 202611 am–4 pmFestivals & celebrationsFood & pairingsDetails

Oct17SatFall Farm Tour at BreauxBreaux Vineyards · PurcellvilleSat, Oct 17, 2026 – Sun, Oct 18, 2026 · Daily11 am hike each day; check in 15 minutes earlyOutdoors & wellnessDetails

Oct17SatVines & Views HikeBreaux Vineyards · PurcellvilleSat, Oct 17, 2026 · Selected dates11 am; approximately one hourWine tastingsOutdoors & wellnessDetails

Oct17SatSip & Savor Wine SocialEchelon Wine Bar · LeesburgSat, Oct 17, 202612 pm–2 pmWine tastingsDetails

Oct17SatDaniel MenshBluemont Station Brewery & Winery · BluemontSat, Oct 17, 20261 pm–4:30 pmLive musicDetails

Oct17SatGrayson MoonBreaux Vineyards · PurcellvilleSat, Oct 17, 20262 pm–5 pmLive musicDetails

Oct17SatMark CullinaneOld 690 Brewing Company · PurcellvilleSat, Oct 17, 20262 pm–5 pmLive musicDetails

Oct17SatMike MallickBluemont Station Brewery & Winery · BluemontSat, Oct 17, 20265 pm–8 pmLive musicDetails

Oct17SatSarah CooperBear Chase Brewing Company · BluemontSat, Oct 17, 20265:30 pm–9 pmLive musicDetails

Oct17SatJumptown at Harvest Gap BreweryHarvest Gap Brewery · HillsboroSat, Oct 17, 20266 pmLive musicDetails

Oct17SatVertical: Chenin Blanc & What Will the Women DrinkWalsh Family Wine · PurcellvilleSat, Oct 17, 20266:30 pm–8:30 pmWine tastingsDetails

Oct17SatLoudoun Fall Farm TourLoudoun County Economic Development / Loudoun FarmsSat, Oct 17, 2026 – Sun, Oct 18, 2026 · DailyHours vary by stop; many farms participate 10 am–4 pm.Outdoors & wellnessDetails

Oct18SunVines & Views HikeBreaux Vineyards · PurcellvilleSun, Oct 18, 2026 · Selected dates11 am; approximately one hourWine tastingsOutdoors & wellnessDetails

Oct18SunScott ClarkBear Chase Brewing Company · BluemontSun, Oct 18, 202612 pm–4 pmLive musicDetails

Oct18SunPaws & Paint: Paint Your Pet868 Estate VineyardsSun, Oct 18, 20261 pm–3:30 pmClasses & workshopsDetails

Oct18SunScott KurtLost Barrel Brewing · MiddleburgSun, Oct 18, 20261 pmLive musicDetails

Oct18SunChris HanksOld 690 Brewing Company · PurcellvilleSun, Oct 18, 20262 pm–5 pmLive musicDetails

Oct18SunJason MasiBreaux Vineyards · PurcellvilleSun, Oct 18, 20262 pm–5 pmLive musicDetails

Oct18SunMatt DavisBluemont Station Brewery & Winery · BluemontSun, Oct 18, 20262 pm–5 pmLive musicDetails

Oct22ThuForest & Field: An Autumn Wine DinnerEchelon Wine Bar · LeesburgThu, Oct 22, 20265 pm–7:45 pmFood & pairingsDetails

Oct23FriVinny GalloBluemont Station Brewery & Winery · BluemontFri, Oct 23, 20265 pm–8 pmLive musicDetails

Oct23FriLoudoun Wine Awards DinnerLoudoun Wineries & Winegrowers Association · LeesburgFri, Oct 23, 20266 pm–10 pmFood & pairingsWine tastingsDetails

Oct24SatBreaux Vineyards Harvest FestivalBreaux Vineyards · PurcellvilleSat, Oct 24, 2026 – Sun, Oct 25, 2026 · Daily11 am–6 pmFestivals & celebrationsLive musicDetails

Oct24SatVines & Views HikeBreaux Vineyards · PurcellvilleSat, Oct 24, 2026 · Selected dates11 am; approximately one hourWine tastingsOutdoors & wellnessDetails

Oct24SatMerry Crispness Fall FestivalWine Reserve at Waterford · WaterfordSat, Oct 24, 202612:00 pm–6:00 pm; last call at 5:45 pmFestivals & celebrationsWine tastings+1 moreDetails

Oct24SatWill BarkleyBluemont Station Brewery & Winery · BluemontSat, Oct 24, 20261 pm–4:30 pmLive musicDetails

Oct24SatRoxanne CookBluemont Station Brewery & Winery · BluemontSat, Oct 24, 20265 pm–8 pmLive musicDetails

Oct24SatAn Evening in StellenboschEndhardt Vineyards · PurcellvilleSat, Oct 24, 20266:30 pmWine tastingsFood & pairingsDetails

Oct25SunFall Market at Bear Chase BrewingBear Chase Brewing Company · BluemontSun, Oct 25, 202611 am–4 pmMarkets & fairsDetails

Oct25SunVines & Views HikeBreaux Vineyards · PurcellvilleSun, Oct 25, 2026 · Selected dates11 am; approximately one hourWine tastingsOutdoors & wellnessDetails

Oct25SuniPhone Photography ClassBreaux Vineyards · PurcellvilleSun, Oct 25, 20261 pm–3 pmClasses & workshopsArts & cultureDetails

Oct25SunLaura CashmanOld 690 Brewing Company · PurcellvilleSun, Oct 25, 20262 pm–5 pmLive musicDetails

Oct25SunPaul BonsieroBluemont Station Brewery & Winery · BluemontSun, Oct 25, 20262 pm–5 pmLive musicDetails

Oct26MonFull Moon Horoscope Tasting: Hunter’s MoonBluemont VineyardMon, Oct 26, 20266 pm–9 pmWine tastingsDetails

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

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

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

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

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

November 202650 listings

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

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

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

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 VineyardSat, Nov 7, 20266–8 p.m.; optional cellar tour at 5 p.m.Festivals & celebrationsWine tastingsDetails

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

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

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 · LeesburgFri, Nov 13, 20269 am–7 pmMarkets & fairsHolidaysDetails

Nov13FriHarvest DinnerSparkling House · 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

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

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

Nov14SatPours to Explore: Sauvignon Blanc & Cabernet FrancLoudoun Wineries & Winegrowers AssociationSat, Nov 14, 20266 pm–8 pmWine tastingsDetails

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

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

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

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

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