Leonardtown Holiday events

Holiday events

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.

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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, 08 Nov

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23976 Point Look...

Holiday Kickoff at the Marketplace
Sat, 06 Dec

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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

24-25 Dec

•

Decades DC

MATZOBALL® WASHINGTON DC XMAS EVE ages 21-49 December 24, 2025
Sun, 31 Aug

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Spirit of Washin...

DC Labor Day Weekend Pier Pressure Yacht Party Cruise

45+ Interested
Sat, 15 Nov

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31640 Winterplac...

Harvest Thyme Craft Fair 2025

17+ Interested
11-12 Oct

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2371 Carl D Silv...

Fall Arts & Crafts Show

31+ Interested
Sun, 31 Aug

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Silver Spring Ci...

Ethiopian Day

12+ Interested
Mon, 01 Sep

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102 S Spring St,...

Marcus Simon's Annual Jim Scott Labor Day BBQ

10+ Interested
31 Oct-01 Nov

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Spirit of Washin...

DC Halloween Party Cruise | Titanic Masquerade

7+ Interested
Sat, 27 Sep

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Fredericksburg F...

The Craft Harvest - Artisan Market

8+ Interested
30-31 Aug

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Wicomico Youth &...

Dinosaur Adventure - Salisbury, MD

6+ Interested

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