Wine Tastings, Dinners & Festivals

Wine Tastings, Dinners & Festivals

Near St. Michaels, Maryland

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Featured Local Events

St Michaels, MD

Simpatico's 15th Annual Italian Wine & Food Festival & More

Sat, October 10, 2026

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All Upcoming Local Events

17 Events listed within 30 miles.

60 miles 30 miles 15 miles
  • Oct 2-9, 2026 (Fri-Fri)
  • Oct 10-17, 2026 (Sat-Sat)
  • Oct 18-25, 2026 (Sun-Sun)
St. Michaels Wine Tasting Cruise!
St. Michaels Sailing Charters | St. Michaels, Maryland
  • Oct 10, 2026 (Sat)
Simpatico's 15th Annual Italian Wine & Food Festival & More
Simpatico Italy's Finest | St Michaels, MD
  • Oct 16, 2026 (Fri)
Soups & Sips
Kent Island Resort | Stevensville, MD
  • Oct 17, 2026 (Sat)
Taste. Toast. & Devour.
16201 Trade Zone Ave | Upper Marlboro, MD
  • Oct 17, 2026 (Sat)
The 3RD Taste Of Prince George's County By AASRA / AASRA Cares Foundation
5725 Crain Hwy | Upper Marlboro, MD
  • Oct 18, 2026 (Sun)
Taste. Toast. & Devour.
16201 Trade Zone Ave | Upper Marlboro, MD
  • Oct 19, 2026 (Mon)
10/19- Annapolis, MD- Dinner After Dark
Cooper’s Hawk Winery & Restaurant | Annapolis, MD
  • Oct 20, 2026 (Tue)
Metropolitan Cigar & Whiskey Night
Metropolitan Kitchen & Lounge | Annapolis, MD
  • Oct 20, 2026 (Tue)
10/20-Annapolis, MD- Dinner After Dark
Cooper’s Hawk Winery & Restaurant | Annapolis, MD
  • Oct 22, 2026 (Thu)
  • Nov 26, 2026 (Thu)
  • Dec 24, 2026 (Thu)
Rum Master Class
Rumhouse | Annapolis, MD
  • Oct 24, 2026 (Sat)
Feast On The Farm: A Celebration Of Conservation
Mas Que Farm | Annapolis, MD
  • Oct 26-Nov 2, 2026 (Mon-Mon)
  • Nov 3-10, 2026 (Tue-Tue)
  • Nov 11-15, 2026 (Wed-Sun)
St. Michaels Wine Tasting Cruise!
St. Michaels Sailing Charters | St. Michaels, Maryland
  • Oct 27, 2026 (Tue)
Mixology 101 – Smoke & Ember
Kent Island Resort | Stevensville, MD
  • Oct 27, 2026 (Tue)
Haunted Dinner In The Dark With Annapolis Ghost Tours
Ashling Kitchen & Bar | Crofton, MD
  • Nov 5, 2026 (Thu)
Chart House Prime - Caymus Wine Dinner
Chart House Prime | Annapolis, MD
  • Nov 19, 2026 (Thu)
Uncork The Holidays Wine Dinner On 11/19 At 6PM ET
Scossa Restaurant | Easton, MD
  • Apr 24-25, 2027 (Sat-Sun)
WineFest At St. Michaels 2027
St. Michaels, Maryland | St. Michaels, Maryland
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Wine, Food & Drink in St. Michaels: Frequently Asked Questions

What is the best source for wine and food events in St. Michaels?

For over 25 years, LocalWineEvents.com has been the definitive go-to source for discovering the best wine, food, and drink events in St. Michaels. From local wine tastings and boutique dinners to large-scale food festivals, we provide the most comprehensive, expert-curated calendar for St. Michaels enthusiasts and professionals.

How can I find upcoming beer and spirits festivals near St. Michaels?

LocalWineEvents.com features a dedicated discovery engine for St. Michaels that includes craft beer festivals, spirits tastings, and distillery tours. As a leading industry resource since 2000, we ensure our St. Michaels listings are updated hourly to help you find the perfect drink experience.