September through November is Loudoun’s peak season: grape harvest, Virginia Wine Month, changing leaves, and some of the year’s busiest tasting-room weekends.
Crush season is a working season
Harvest does not mean every visitor gets a behind-the-scenes crush tour. Crews may be picking early, sorting fruit, moving equipment, or closing production areas while the tasting room runs normally. Treat any public grape-stomp, harvest dinner, barrel tasting, or release as an event that needs its own confirmed listing and reservation.
Foliage and vineyard views
Our active records with a published view note or best-views facet include Stone Tower Winery, Willowcroft Farm Vineyards, Casanel Vineyards & Winery, Zephaniah Farm Vineyard, Lost Creek Winery (Echelon Wine Bar), 868 Estate Vineyards, Breaux Vineyards, Sunset Hills Vineyard, Walsh Family Wine, Doukénie Winery. Start with the best-view wineries, then confirm patio access and weather plans with each venue.
Dated and confirmed
Fall harvest, release, and festival events
Only future events with a published date in September, October, or November appear here. Confirm the official event page before driving.
Bluemont Crush With Us
Bluemont Vineyard
Grape-stomping harvest event on September weekends at Bluemont Vineyard.
Add to calendar (opens in new tab)Download ICSVenue details — Bluemont Crush With UsOfficial page — Bluemont Crush With Us (opens in new tab)
LoCo Fest at 868 Estate
868 Estate Vineyards
868 Estate Vineyards’ marquee early-fall music festival, LoCo Fest — an all-day (noon–9pm) day of live music at the Purcellville vineyard.
Add to calendar (opens in new tab)Download ICSVenue details — LoCo Fest at 868 EstateTickets — LoCo Fest at 868 Estate (opens in new tab)Official page — LoCo Fest at 868 Estate (opens in new tab)
Bear Chase Oktoberfest
Bear Chase Brewing Company
Bear Chase's annual Oktoberfest at the Bluemont brew barn — market vendors, live music, and their gold-medal Oktoberfest Marzen lager.
Add to calendar (opens in new tab)Download ICSVenue details — Bear Chase OktoberfestOfficial page — Bear Chase Oktoberfest (opens in new tab)
Bluemont Fair
Bluemont Community Center
Traditional country fair in the village of Bluemont.
Add to calendar (opens in new tab)Download ICSOfficial page — Bluemont Fair (opens in new tab)
Lovettsville Oktoberfest
Downtown Lovettsville
Town-wide German-heritage Oktoberfest festival in Lovettsville.
Add to calendar (opens in new tab)Download ICSOfficial page — Lovettsville Oktoberfest (opens in new tab)
Leesburg Airshow
Leesburg Executive Airport
Free late-September airshow at Leesburg Executive Airport with aerial performances and ground attractions.
Add to calendar (opens in new tab)Download ICSOfficial page — Leesburg Airshow (opens in new tab)
Great Country Farms Fall Pumpkin Harvest
Great Country Farms
Great Country Farms’ month-long Fall Pumpkin Harvest in Bluemont — pick-your-own pumpkins, corn maze and apple harvest, next door to Bear Chase and Dirt Farm.
Add to calendar (opens in new tab)Download ICSOfficial page — Great Country Farms Fall Pumpkin Harvest (opens in new tab)
Waterford Fair
Historic Waterford Village
Virginia's oldest crafts fair, early October, in historic Waterford.
Add to calendar (opens in new tab)Download ICSOfficial page — Waterford Fair (opens in new tab)
Loudoun Wine Awards
Lansdowne Resort & Spa
October gala honoring Loudoun’s Winemaker / Winegrower / Wine Ambassador of the Year; Grand Tasting at 6pm at Lansdowne Resort.
Add to calendar (opens in new tab)Download ICSOfficial page — Loudoun Wine Awards (opens in new tab)
Harvest Festival at Breaux
Breaux Vineyards
Breaux Vineyards’ fall Harvest Festival weekend at the Purcellville estate.
Add to calendar (opens in new tab)Download ICSVenue details — Harvest Festival at BreauxOfficial page — Harvest Festival at Breaux (opens in new tab)
LoCo Wine Festival – Fall
Old Farm Winery at Hartland
Fall edition of the Loudoun wine festival at Old Farm Winery at Hartland, with wine tastings, food trucks, live music, and an artisan market.
Add to calendar (opens in new tab)Download ICSOfficial page — LoCo Wine Festival – Fall (opens in new tab)
Build a fall day without racing the clock
Saturday afternoons can book up quickly in peak foliage weeks. Use the reservation filter, keep rural drives short, and give working harvest crews space. For a ready-made route, follow the Best Views Day or choose the tighter Blue Ridge Ridge Trail.