Holiday events in Chestertown 2025

Holiday markets fairs, activities & things to do in Chestertown, Maryland

Discover the best Holiday events in Chestertown! From festive Christmas markets to New Year's Eve fireworks displays & Holiday Bazaar, we have something for everyone. Explore the Chestertown's winter attractions and make lasting memories with friends and family. With so much to do in Chestertown, you'll never have a dull moment this holiday season.

Holiday events in Chestertown

Holiday events in Chestertown

Sun, 07 Sep

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25227 Chestertown Rd

Brampton 1860 Fall Open House

Holiday events from nearby cities

Sat, 01 Nov

•

Blueberry Garden...

Calm From The Chaos: A Restorative Yoga & SoulCollage Reset
Thu, 02 Oct

•

Baltimore City H...

JAZZY SUMMER NIGHT SERIES FINALE FEATURING DRU HILL

49+ Interested
26-28 Sep

•

Tanger Rehoboth ...

Foodees Food and Culture Festival, Rehoboth Beach, Delaware

15+ Interested
Sun, 31 Aug

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Spirit of Baltim...

Baltimore Labor Day Sunday Pier Pressure White Party Cruise

10+ Interested
Sat, 16 Aug

•

706 Agriculture ...

Heirloom Tomato Festival at the Carroll County Farmer's Market

6+ Interested
Sat, 16 Aug

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POWER PLANT LIVE!

Bingo Loco

6+ Interested
Sat, 16 Aug

•

1745 Baltimore B...

2025 Reese VFC 21st Annual Car & Truck Show
Sun, 31 Aug

•

Spirit of Washin...

DC Labor Day Weekend Pier Pressure Yacht Party Cruise

10+ Interested
Sat, 23 Aug

•

Hudson Fields

Saltwater Luau

4+ Interested

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Holiday events from nearby cities