Leonardtown Holiday events

Holiday events in Leonardtown Today

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.

|

Community Member

Community Member

Community Member

Join 232.1k+ Fellow Explorers

Holiday events in Leonardtown Today

Holiday events in Leonardtown Today

Thu, 11 Dec, 2025 - 06:00 PM

Tinsel and Tape: Holiday Wrapping Workshop

The Fenwick Inn

USD 8
Thu, 11 Dec, 2025 - 11:00 AM

Extended Thursday Hours for Holiday Shopping!

22660 Washington St., Leonardtown, MD, United States, Maryland 20650

Explore events by date

calendar_icon

calendar_icon

calendar_icon

Custom Date

Pick Range

calendar_icon

Holiday events from nearby cities

Featured

Sat, 13 Dec • 08:00 PM

Holiday Improv Comedy Show - Falls Church, Virginia

The Center for Spiritual Enlightenment

23+ Interested

|

USD 10
Sat, 13 Dec • 12:00 PM

🌟 🎄 2nd Annual Holiday Craft Fair & Toy Drive! 🎁 🎅

iLove Events Center

5+ Interested

|

Free
Featured

Sat, 20 Dec • 08:00 PM

Holiday Improv Comedy Show - Annapolis Maryland

ArtFarm

Newly Added

|

USD 10
Sat, 13 Dec • 07:00 PM

BLACK TIE ROMAN HOLIDAY GALA AT THE EMBASSY OF ITALY

Embassy of Italy

4+ Interested

|

USD 125
Sun, 14 Dec • 05:00 PM

Toys for Shelter Pets – Second Annual Christmas Charity Event

Hotel Hive

Newly Added

|

USD 15
Wed, 24 Dec • 09:00 PM

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

Decades DC

Newly Added

|

USD 40
Sat, 13 Dec • 11:00 AM

Old Town Alexandria Christmas Market and Holiday Craft Show

John Carlyle Square

18+ Interested

|

Free
Sat, 13 Dec • 04:00 PM

Downtown Cookie Crawl

601 Caroline Street, Fredericksburg, VA, United States, Virginia 22401

2894+ Interested
Sat, 13 Dec • 07:00 PM

A Very Merry Soulful Christmas Party

Meadow Event Park, Farm Bureau Center

201+ Interested

Explore Events around you

10 km

5 km

10 km

25 km

50 km

Loading events...

Leonardtown's Most-Loved

Music events in Leonardtown Today

Parties in Leonardtown Today

Food & Drinks events in Leonardtown Today

Health & Wellness events in Leonardtown Today

Kids events in Leonardtown Today

Sports events in Leonardtown Today

Christmas events in Leonardtown Today

New Year events in Leonardtown Today

Trips & Adventure events in Leonardtown Today

All Categories

All Events that you vibe with!

Customize your experience; only see the events that click with you!

Best in Leonardtown, straight to your inbox

Never miss a single fun event; let us keep you updated!

Explore more in Leonardtown

Holiday events from nearby cities