Annual Festivals
Mark Your Calendar for Unforgettable Experiences
From waterfront parades to celebrations of seafood and music, Talbot County has annual festivals that will bring you back year after year. Plan your trip around signature moments like Easton’s world-renowned Waterfowl Festival and the creative magic of summer’s Plein Air Easton, or drop into charming St. Michaels, Oxford, and Tilghman Island for maritime celebrations, boat shows, and live music. Browse by the category that interests you, or explore our full events calendar to plan your trip.
Arts & Culture
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February 20 – February 21
Chesapeake Fire & Ice Festival
Every February, downtown Easton transforms into a sparkling winter wonderland — with glowing fire pits, dazzling ice sculptures, live music, and warm community spirit — at the Chesapeake Fire & Ice Festival. The 2026 event kicks off at 5 p.m. on Friday, Feb. 20 and concludes on Saturday, Feb. 21 at 8 p.m. What to…
Feb
20
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Jul
11
July 11 – July 20
Plein Air Easton
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Nov
14
November 14 – November 16
Waterfowl Festival
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Nov
22
November 22
Eastern Shore Sea Glass and Coastal Arts Festival
Maritime Events
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August 30 – August 30 | 8am
Chesapeake Bay Maritime Museum Annual Charity Boat Auction
Bid on adventure at the Chesapeake Bay Maritime Museum’s Annual Charity Boat Auction, a waterfront tradition where donated boats find new homes and every sale supports maritime education and preservation.
Aug
30
Recreation Events
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November 8
Historic Drawbridge Running Festival
Run across Talbot County’s historic drawbridges on a fast, waterfront course with big views, great vibes, and a post-race celebration.
Nov
08
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May
17
May 17
St. Michaels Running Festival
Food & Wine
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April 25 – April 26
Winefest at St. Michaels
Sample wines from across the globe during WineFest at St. Michaels. Compare flavor profiles, explore production processes, and chat with winemakers. Blending maritime character with small-town elegance, the historic streets of St. Michaels offer the perfect backdrop for sampling, sipping, and savoring wine. What to Expect The festival has continued to evolve and grow since its…
Apr
25
Holidays & Seasonal Events
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November 26 – November 27
Holiday Events in Talbot County
With twinkling lights illuminating town streets, candlelit dinners by warm fireplaces, horse-drawn carriage rides, and shops decorated for Christmas, you’re sure to be jolly and ready to join in the many holiday events and activities.
Nov
26
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Dec
31
December 31
New Year’s Eve in Talbot County
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Jul
04
July 4
Independence Day in Talbot County
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Jun
20
June 20 – July 4
Easton Carnival and July 4th Fireworks
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Mar
17
March 17 – March 17
St. Patrick’s Day in Downtown Easton