Chestertown Holiday events

Holiday events in Chestertown

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.

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Holiday events in Chestertown

Holiday events in Chestertown

Fri, 05 Dec

Kids' Nights: Holiday Movie Night (Ages 2-11)

151 Dixon Drive Suite 4, Chestertown, MD, United States, Maryland 21620

Holiday events from nearby cities

Sun, 14 Dec

40th Annual Cookie Tour of Historic Homes

Union Square
Sat, 01 Nov

Calm From The Chaos: A Restorative Yoga & SoulCollage Reset

Blueberry Gardens Center for Yoga, Growth, and Healing

Newly Added

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USD 85
Editor's pick

Thu, 23 Oct

Food Tasting and Diwali Celebration

Vedic Health
Sat, 13 Dec

Canton’s Biggest Santa Bar Fest

1021 S Linwood Ave

Newly Added

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USD 10
Sat, 13 Dec

The Worthington's Bad Santa Day Party

2900 O'Donnell St
24-25 Dec

MATZOBALL® WASHINGTON DC XMAS EVE ages 21-49 December 24, 2025

Decades DC
Sun, 02 Nov

Brandy, Monica, Kelly Rowland, Muni Long in Baltimore

CFG Bank Arena

10+ Interested
Sat, 11 Oct

Fall Harvest Fest

36470 Seaside Outlet Dr, 19971

32+ Interested
Sat, 25 Oct

Maryland Crabcake Festival 2025

Carroll County Farm Museum

76+ Interested

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