Holiday events in Leonardtown 2025

Holiday markets fairs, activities & things to do in Leonardtown

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

Holiday events in Leonardtown

Holiday events in Leonardtown

Sat, 29 Nov

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Town Market LLC

Small Business Saturday with The Grinch & Cindy Lou Who
Sat, 06 Dec

•

22675 Washington...

Fur Babies with the Grinch and Holiday Market
Sat, 20 Dec

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Town Market LLC

Pictures with Santa Clause
Fri, 28 Nov

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Town Market LLC

Holiday Market with The Grinch & Cindy Lou Who

Holiday events from nearby cities

09-10 Aug

•

Space DC Restaur...

DC'S Fake Telugu Wedding (Pelli) Party @Space Rooftop
11-12 Oct

•

2371 Carl D Silv...

Fall Arts & Crafts Show

23+ Interested
Sat, 15 Nov

•

31640 Winterplac...

Harvest Thyme Craft Fair 2025

12+ Interested
Sun, 31 Aug

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Spirit of Washin...

DC Labor Day Weekend Pier Pressure Yacht Party Cruise

10+ Interested
Sun, 31 Aug

•

Silver Spring Ci...

Ethiopian Day

8+ Interested
31 Oct-01 Nov

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Spirit of Washin...

DC Halloween Party Cruise | Titanic Masquerade

4+ Interested
16-17 Aug

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Town Hill, Colon...

46th Annual Rod Run to the Beach
Sat, 27 Sep

•

Fredericksburg F...

The Craft Harvest - Artisan Market

5+ Interested
Sat, 08 Nov

•

Chesapeake High ...

2025 Fall Craft Fair

12+ Interested

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