Events & happenings

A curated list of live music, tastings, classes, dinners, festivals, outdoor events and local gatherings across Northern Virginia wine country. This is not a comprehensive list of everything going on in the area. For a more comprehensive list, scroll to the bottom and click the links under the Keep Exploring section.

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Fri, Oct 16, 2026 – Sun, Oct 18, 2026 · Virginia time · Friday–Sunday

18 events

October 202618 events

Fri, Oct 16, 2026

Sat, Oct 17, 2026

Sun, Oct 18, 2026

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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 202618 events

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

Oct16FriCelebrate PurcellvilleTown of Purcellville · PurcellvilleSat, Oct 10, 2026 – Sat, Oct 17, 2026 · DailyActivities daily; times vary. Finale October 17, 2–5 pm.Festivals & celebrationsDetails

Oct16FriMiddleburg Film FestivalMiddleburg Film Festival · MiddleburgThu, Oct 15, 2026 – Sun, Oct 18, 2026 · DailyScreenings daily; times vary by film and venue.Festivals & celebrationsArts & cultureDetails

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, 202611 am; organizer lists an 11 am–1 pm window, with an approximately one-hour hike.Wine tastingsOutdoors & wellnessDetails

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

Oct17SatMark CullinaneOld 690 Brewing Company · PurcellvilleSat, Oct 17, 20262 pm–5 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, 202611 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

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