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Winery Events and Things to do in Leesburg, VA

Boxwood Estate Winery's 6th Annual Oyster Riot
Sunday at 12:00 PM
Virginia · Boxwood Estate Winery
Boxwood Estate Winery's 6th Annual Oyster Riot
Sunday at 12:00 PM
Virginia · Boxwood Estate Winery
B.Y.O.W.—Blend Your Own Wine Party
Sat, Oct 17, 1:00 PM
Virginia · 8 Chains North Winery
B.Y.O.W.—Blend Your Own Wine Party
Sat, Oct 17, 1:00 PM
Virginia · 8 Chains North Winery
Sales end soon
Haunted Nights at Twin Oaks: Ghost Tour & Wine Tasting
Saturday at 6:30 PM + 7 more
Virginia · Twin Oaks Tavern Winery
Sales end soon
Haunted Nights at Twin Oaks: Ghost Tour & Wine Tasting
Saturday at 6:30 PM + 7 more
Virginia · Twin Oaks Tavern Winery
Petals & Poses
Sun, Oct 18, 9:30 AM
Virginia · Cana Vineyards and Winery of Middleburg
Petals & Poses
Sun, Oct 18, 9:30 AM
Virginia · Cana Vineyards and Winery of Middleburg
Almost full
2026 Loudoun Wine Awards Dinner
Fri, Oct 23, 6:00 PM
Lansdowne · Lansdowne Resort
Almost full
2026 Loudoun Wine Awards Dinner
Fri, Oct 23, 6:00 PM
Lansdowne · Lansdowne Resort
Just added
Dinner with Àimore: Masterchef Kitchen Takeover at Twin Oaks
Sat, Nov 7, 4:00 PM
Virginia · Twin Oaks Tavern Winery
Just added
Dinner with Àimore: Masterchef Kitchen Takeover at Twin Oaks
Sat, Nov 7, 4:00 PM
Virginia · Twin Oaks Tavern Winery
Just added
AWARD WINNING MARYLAND WINE-Governor's Cup Winners Celebration
Thu, Nov 5, 5:30 PM
Darnestown · Windridge Vineyards
Just added
AWARD WINNING MARYLAND WINE-Governor's Cup Winners Celebration
Thu, Nov 5, 5:30 PM
Darnestown · Windridge Vineyards
Selling fast
Pours to Explore Tasting Series: Sauvignon Blanc & Cabernet Franc
Sat, Nov 14, 6:00 PM
Virginia · Bluemont Vineyard
Selling fast
Pours to Explore Tasting Series: Sauvignon Blanc & Cabernet Franc
Sat, Nov 14, 6:00 PM
Virginia · Bluemont Vineyard
Loudoun Wine Nights - October 28, 2026
Wed, Oct 28, 6:30 PM
Virginia · Washington Dulles Airport Marriott
Loudoun Wine Nights - October 28, 2026
Wed, Oct 28, 6:30 PM
Virginia · Washington Dulles Airport Marriott
Friendsgiving Guided Food and Wine Pairing
Sat, Nov 14, 5:00 PM
Virginia · Twin Oaks Tavern Winery
Friendsgiving Guided Food and Wine Pairing
Sat, Nov 14, 5:00 PM
Virginia · Twin Oaks Tavern Winery
Almost full
10/19- Rockville, MD- Dinner After Dark
Mon, Oct 19, 7:00 PM
Glenora Hills · Cooper’s Hawk Winery & Restaurant
Almost full
10/19- Rockville, MD- Dinner After Dark
Mon, Oct 19, 7:00 PM
Glenora Hills · Cooper’s Hawk Winery & Restaurant
Boo’d Up: A Couples Halloween Experience
Sat, Oct 24, 5:00 PM
Virginia · Fleetwood Farm Winery
Boo’d Up: A Couples Halloween Experience
Sat, Oct 24, 5:00 PM
Virginia · Fleetwood Farm Winery
Local Goat Cheese & Wine Pairing with baby goat bottle feeding
Sat, Oct 24, 3:00 PM
Maryland · Bluffing Goat Farm
Local Goat Cheese & Wine Pairing with baby goat bottle feeding
Sat, Oct 24, 3:00 PM
Maryland · Bluffing Goat Farm
Mahjong at the Vineyard | Winery at La Grange
Sat, Oct 24, 1:00 PM
Virginia · The Winery at La Grange
Mahjong at the Vineyard | Winery at La Grange
Sat, Oct 24, 1:00 PM
Virginia · The Winery at La Grange
Almost full
11/16- Rockville, MD- Friendsgiving in Wine Country
Mon, Nov 16, 7:00 PM
Glenora Hills · Cooper’s Hawk Winery & Restaurant
Almost full
11/16- Rockville, MD- Friendsgiving in Wine Country
Mon, Nov 16, 7:00 PM
Glenora Hills · Cooper’s Hawk Winery & Restaurant
Friendsgiving @ The Winery
Sat, Nov 28, 1:00 PM
Virginia · The Winery at Bull Run - The Barrel Room
Friendsgiving @ The Winery
Sat, Nov 28, 1:00 PM
Virginia · The Winery at Bull Run - The Barrel Room
Hands-On Korean BBQ Cooking Class at Sugarloaf Mountain Vineyard
Thu, Oct 22, 6:00 PM
Maryland · Sugarloaf Mountain Vineyard
Hands-On Korean BBQ Cooking Class at Sugarloaf Mountain Vineyard
Thu, Oct 22, 6:00 PM
Maryland · Sugarloaf Mountain Vineyard
Windridge Winery Client Appreciation evening!
Mon, Oct 12, 4:00 PM
Darnestown · Windridge Vineyards
Windridge Winery Client Appreciation evening!
Mon, Oct 12, 4:00 PM
Darnestown · Windridge Vineyards
Sales end soon
DC Gator Winery & Cidery Event
Sat, Oct 24, 10:00 AM
Pentagon City · Fashion Centre at Pentagon City
Sales end soon
DC Gator Winery & Cidery Event
Sat, Oct 24, 10:00 AM
Pentagon City · Fashion Centre at Pentagon City
Fall-Themed Paint & Sip with Artist Heather Connole
Sun, Oct 25, 12:00 PM
Virginia · 8 Chains North Winery
Fall-Themed Paint & Sip with Artist Heather Connole
Sun, Oct 25, 12:00 PM
Virginia · 8 Chains North Winery

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