Wine Tastings, Dinners & Festivals

Wine Tastings, Dinners & Festivals

Near St. Michaels, Maryland

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Premium Event

2026 Winefest At St. Michaels
  • Sat, April 25, 2026 to Sun, April 26, 2026
St. Michaels, MD
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Featured Local Events

St. Michaels, MD

2026 Winefest At St. Michaels

Sat, April 25, 2026 to Sun, April 26, 2026

View details

All Upcoming Local Events

22 Events listed within 30 miles.

60 miles 30 miles 15 miles
  • Mar 21, 2026 (Sat)
Pamper & Pour: Candle Making Experience
Far Eastern Shore Winery | Easton, MD
  • Mar 22, 2026 (Sun)
Exclusive Winery Tour & Wine Tasting (March 22nd, 2:00-3:30pm)
Robin Hill Farm and Vineyards | Brandywine, MD
  • Mar 28, 2026 (Sat)
Wine And Food Pairing Italian Brunch Cookery 12 Noon Class
Simpatico, Italy's Finest | St. Michael's, MD
  • Mar 28, 2026 (Sat)
Wine And Food Pairing Italian Brunch Cookery 2 PM Class
Simpatico, Italy's Finest | St. Michael's, MD
  • Mar 29, 2026 (Sun)
Spring Afternoon Tea At The Maryland Inn
The Maryland Inn of the Historic Inns of Annapolis | Annapolis, MD
  • Mar 29, 2026 (Sun)
Exclusive Winery Tour & Wine Tasting (March 29th, 2:00-3:30pm)
Robin Hill Farm and Vineyards | Brandywine, MD
  • Apr 2, 2026 (Thu)
The Renaissance Rum Club
Rumhouse | Annapolis, MD
  • Apr 4, 2026 (Sat)
  • Jun 6, 2026 (Sat)
  • Aug 8, 2026 (Sat)
  • Sep 12, 2026 (Sat)
Hike And Wine Tasting On The Maryland Wine Trail
Hike and Wine Tasting in Southern Maryland at Jefferson National Park and Perigueax Winery | St. Leonard, MD
Buy Tickets
  • Apr 7, 2026 (Tue)
Spring Wine Tasting - With Allie Balin
209 N Talbot St | Saint Michaels, MD
  • Apr 8, 2026 (Wed)
Rosé Soirée
Wrabyn Boutique | Annapolis, MD
  • Apr 11, 2026 (Sat)
Tie Dye Sip And Swirl
Far Eastern Shore Winery | Easton, MD
  • Apr 17-24, 2026 (Fri-Fri)
  • Apr 25-May 2, 2026 (Sat-Sat)
  • May 3-10, 2026 (Sun-Sun)
  • May 11-18, 2026 (Mon-Mon)
Wine Tasting Cruise On Historic Lady Patty!
St. Michaels Sailing Charters | St. Michaels, Maryland
  • Apr 17-24, 2026 (Fri-Fri)
  • Apr 25-May 2, 2026 (Sat-Sat)
  • May 3-10, 2026 (Sun-Sun)
  • May 11-18, 2026 (Mon-Mon)
St. Michaels Wine Tasting Cruise!
St. Michaels Sailing Charters | St. Michaels, Maryland
  • Apr 25-26, 2026 (Sat-Sun)
2026 Winefest At St. Michaels
Winefest at St. Michaels | St. Michaels, MD
Buy Now
  • Apr 30, 2026 (Thu)
The Renaissance Rum Club
Rumhouse | Annapolis, MD
  • May 19-26, 2026 (Tue-Tue)
  • May 27-Jun 3, 2026 (Wed-Wed)
  • Jun 4-11, 2026 (Thu-Thu)
  • Jun 12-19, 2026 (Fri-Fri)
St. Michaels Wine Tasting Cruise!
St. Michaels Sailing Charters | St. Michaels, Maryland
  • Jun 4, 2026 (Thu)
The Renaissance Rum Club
Rumhouse | Annapolis, MD
  • Jun 20-27, 2026 (Sat-Sat)
  • Jun 28-Jul 5, 2026 (Sun-Sun)
  • Jul 6-13, 2026 (Mon-Mon)
  • Jul 14-21, 2026 (Tue-Tue)
St. Michaels Wine Tasting Cruise!
St. Michaels Sailing Charters | St. Michaels, Maryland
  • Jul 22-29, 2026 (Wed-Wed)
  • Jul 30-Aug 6, 2026 (Thu-Thu)
  • Aug 7-14, 2026 (Fri-Fri)
  • Aug 15-22, 2026 (Sat-Sat)
St. Michaels Wine Tasting Cruise!
St. Michaels Sailing Charters | St. Michaels, Maryland
  • Aug 23-30, 2026 (Sun-Sun)
  • Aug 31-Sep 7, 2026 (Mon-Mon)
  • Sep 8-15, 2026 (Tue-Tue)
  • Sep 16-23, 2026 (Wed-Wed)
St. Michaels Wine Tasting Cruise!
St. Michaels Sailing Charters | St. Michaels, Maryland
  • Sep 24-Oct 1, 2026 (Thu-Thu)
  • 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 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

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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.