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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July 11 – July 20
Plein Air Easton
Held in Maryland each July, Plein Air Easton (PAE) is the largest and most prestigious juried plein air painting competition in the United States.
Jul
11
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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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Feb
20
February 20 – February 21
Chesapeake Fire & Ice Festival
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Apr
26
April 26
Celebrate Oxford Day
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May
02
May 2 – May 2
A Quick Guide to the Multicultural Festival
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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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Apr
18
April 18-19, 2026
Eastern Shore Sea Glass and Coastal Arts Festival
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Nov
13
November 13 – November 15
Plan Your Visit to the 2026 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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Jun
19
June 19 – June 21
Explore the Antique & Classic Boat Festival and Coastal Arts Fair – 2026
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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
06
November 6 – June 6 | 8am
Tour de Talbot
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Nov
08
November 8
Historic Drawbridge 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
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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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May 10
Talbot County Mother’s Day Guide: Cherished Moments Await
This Mother’s Day, treat your mom to an extra special day in Talbot County by exploring our historic towns offering small-town charm, a vibrant arts scene, and exceptional local cuisine.
May
10
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Mar
17
March 17 – March 17
St. Patrick’s Day in Talbot County
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Apr
05
April 5 – April 5
Hop into the Spring Season – 2026
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Jun
20
June 20 – June 20
Juneteenth Celebration 2026
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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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Nov
26
November 26 – December 31
Holiday Events in Talbot County
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Dec
31
December 31
New Year’s Eve in Talbot County – 2026/27