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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April 18-19, 2026
Eastern Shore Sea Glass and Coastal Arts Festival
The Eastern Shore Sea Glass and Coastal Arts Festival attracts nearly 100 artisans from up and down the East Coast. These artisans converge on the campus of the Chesapeake Bay Maritime Museum to exhibit and sell their work.
Apr
18
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Apr
26
April 26
Celebrate Oxford Day
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Jun
12
June 12 – June 20
Chesapeake Chamber Music Festival
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Oct
08
October 8 – October 10
Chesapeake Film Festival
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Feb
20
February 20 – February 21
Chesapeake Fire & Ice Festival
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Jul
11
July 11 – July 20
Plein Air Easton
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Jan
01
January 1 – December 31
Talbot250: Honoring the Past, Celebrating the Present, and Shaping the Future
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Nov
14
November 14 – November 16
Waterfowl Festival
Maritime Events
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June 27 – September 20
Chesapeake Bay Log Canoe Races
From June through September, the Chesapeake Bay’s fleet of log canoes stages a weekly water ballet, as a delicate flotilla of century-old sailboats competes for bragging rights.
Jun
27
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Aug
30
August 30 – August 30 | 8am
Chesapeake Bay Maritime Museum Annual Charity Boat Auction
Recreation Events
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May
Tri-County Ice Cream Classic
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May
02
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Nov
08
November 8
Historic Drawbridge Running Festival
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Nov
06
November 6 – June 6 | 8am
Tour de Talbot
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
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Mar
07
March 7
Sweet Times Ahead – St. Michaels ChocolateFest Returns
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Apr
26
April 26
Taste of Easton – A Celebration of Culinary Excellence
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Nov
07
November 7
Oysterfest at the Chesapeake Bay Maritime Museum
Holidays & Seasonal Events
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April 5 – April 5
Hop into the Spring Season – 2026
Whether you’re looking for an Easter brunch spot, a sweet treat to bring to a family gathering, or activities for the children – we have you covered.
Apr
05
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Nov
26
November 26 – December 31
Holiday Events in Talbot County
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Mar
17
March 17 – March 17
St. Patrick’s Day in Talbot County
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Jun
20
June 20 – July 4
Easton Carnival and July 4th Fireworks
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Jul
04
July 4
Independence Day in Talbot County
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May
10
May 10
Mother’s Day in Talbot County
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Dec
31
December 31
New Year’s Eve in Talbot County – 2026/27