Wine Events and Things to do in Annapolis, MD
Wine events and things to do in Annapolis, MD offer a lively way to explore local tasting rooms, waterfront pairings, and seasonal gatherings. Historic downtown taverns and open-air dining corridors frequently host social tastings that highlight regional vineyards. Educational classes and casual meetups provide approachable pathways for enthusiasts to deepen their appreciation.
- Historic downtown streets and the West Street arts corridor provide walkable settings for spontaneous evening tastings and restaurant pairings.
- Mid-week community gatherings highlight regional selections alongside seasonal outdoor dining experiences.
- Waterfront venues across the area regularly feature specialized bottle releases and guided educational sessions for novices and collectors alike.
11/16- Annapolis, MD- Friendsgiving in Wine Country
Mon, Nov 16, 7:00 PM
Annapolis · Cooper’s Hawk Winery & Restaurant
11/16- Annapolis, MD- Friendsgiving in Wine Country
Mon, Nov 16, 7:00 PM
Annapolis · Cooper’s Hawk Winery & Restaurant
Field and Tide: A Culinary Festival at The Wildset
Tomorrow at 6:30 PM + 1 more
Saint Michaels · 113 North St
Field and Tide: A Culinary Festival at The Wildset
Tomorrow at 6:30 PM + 1 more
Saint Michaels · 113 North St
Pi Omega Chapter Presents: OWTOBER FEST – A Libations Ball
Sat, Dec 19, 3:00 PM
Baltimore · War Memorial Plaza
Pi Omega Chapter Presents: OWTOBER FEST – A Libations Ball
Sat, Dec 19, 3:00 PM
Baltimore · War Memorial Plaza
Southern Maryland Chain Chapter Presents: Sweater & Sips Wine Tasting
Sat, Nov 14, 1:00 PM
Brandywine · Robin Hill Farm and Vineyards
Southern Maryland Chain Chapter Presents: Sweater & Sips Wine Tasting
Sat, Nov 14, 1:00 PM
Brandywine · Robin Hill Farm and Vineyards
Old Westminster Wine Dinner at Marsā Coastal Kitchen
Thu, Nov 12, 6:00 PM
Sparrows Point · Marsā Coastal Kitchen
Old Westminster Wine Dinner at Marsā Coastal Kitchen
Thu, Nov 12, 6:00 PM
Sparrows Point · Marsā Coastal Kitchen
2026 ULTIMATE TAILGATE SEASON PASS — 6 HOME GAMES REMAINING
Sunday at 9:00 AM + 4 more
Hyattsville · 8511 Landover Rd
2026 ULTIMATE TAILGATE SEASON PASS — 6 HOME GAMES REMAINING
Sunday at 9:00 AM + 4 more
Hyattsville · 8511 Landover Rd
Autumn Harvest Brunch | A Luxe Baltimore Brunch Experience at The Oaks
Sat, Nov 21, 11:00 AM
Baltimore · 50 Albemarle St
Autumn Harvest Brunch | A Luxe Baltimore Brunch Experience at The Oaks
Sat, Nov 21, 11:00 AM
Baltimore · 50 Albemarle St
Authentic Italian Pasta - Cooking Class by Classpop!™
Sun, Jan 3, 1:00 PM + 1 more
Baltimore · Location provided after booking
Authentic Italian Pasta - Cooking Class by Classpop!™
Sun, Jan 3, 1:00 PM + 1 more
Baltimore · Location provided after booking
Frequently asked questions about Annapolis