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Leonardtown
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Popular Events in Leonardtown, MD
Dec
5
Vendor or Sponsor Registration for Home for The Holidays
Dec 05, 2026 04:00 PM - 09:00 PM
Saint Mary's Fairgrounds
23.11 USD - 750.00 USD
Nov
15
SKYBOX & THE BAAC MEDIA PRESENTS LANEPUSHERS IN MY OWN LANE (MARYLAND)
Nov 14, 2026 07:00 PM - 11:30 PM
22725 Duke Street
12.51 USD - 28.52 USD
Nov
10
Watercolor Blooms Painting Party
Nov 10, 2026 05:00 PM - 07:30 PM
22694 Washington Street
55.20 USD
Nov
27
Letters to Santa
Nov 27, 2026 06:00 AM
22675 Washington Street
Nov
28
Small Business Saturday with The Grinch & Cindy Lou Who
Nov 28, 2026 04:00 AM - 11:00 AM
Town Market LLC
Dec
5
Family Friendly Event: Santa At The Rex Theatre!
Dec 05, 2026 07:00 AM - 11:00 AM
22695 Washington St
Nov
19
St. Mary's County Early Learning Center Fall Fest & Community Open House
Nov 19, 2026 05:00 PM - 07:00 PM
St. Mary's County Early Center
Free
Dec
5
Home for The Holidays - A New St. Mary's County Holiday Tradition
Dec 05, 2026 04:00 PM - 09:00 PM
Saint Mary's Fairgrounds
8.00 USD
Nov
17
Bookgiving Silent Reading party
Nov 17, 2026 06:00 PM - 08:00 PM
Antoinette’s Garden
Free
Dec
6
Photos with Grinch! (Pet **all species** and kid friendly)
Dec 06, 2026 06:00 AM - 08:00 AM
Balanced Paws Pet Care
Leonardtown, MD · Latest Local
Events
Upcoming
Weekend
New
Nov
10
Watercolor Blooms Painting Party
Nov 10, 2026 05:00 PM - 07:30 PM
22694 Washington Street
55.20 USD
Nov
10
TACO TUESDAY AT THE IRONWOOD GRILL!
Nov 10, 2026 12:00 PM - 03:00 PM
21935 Society Hill Rd
Nov
11
Veterans Day 2026 - Free Admission for all Veterans
Nov 11, 2026 05:00 AM - 12:00 PM
22156 Three Notch Rd
Nov
10
Give Thanks Porch Leaner Painting Event at Antietam Brewery
Nov 10, 2026 06:30 PM - 09:00 PM
Antietam Brewery
55.20 USD
Nov
11
The Everly Brothers Experience ft. the Zmed Brothers
Nov 10, 2026 07:00 PM - 09:00 PM
Live At Hub City Vinyl
30.56 USD - 48.06 USD
Nov
10
Book Bedazzle
Nov 10, 2026 05:30 PM - 07:00 PM
Next Chapter Cafe & Book Shop
39.19 USD
Nov
10
Thanksgiving Wine Glasses Painting Event at Antietam Brewery
Nov 10, 2026 06:30 PM - 09:00 PM
Antietam Brewery
28.52 USD
Nov
10
Costa's Paint Night
Nov 10, 2026 06:00 PM - 08:00 PM
Costas Inn
33.85 USD - 55.20 USD
Nov
10
Downtown Partnership's Annual Meeting
Nov 10, 2026 06:00 PM - 10:00 PM
The BudLight Talon at M&T Bank Stadium
124.56 USD - 215.26 USD
Nov
10
Hands-on Home Canning Workshop: Jams & Jellies
Nov 10, 2026 02:00 PM - 05:00 PM
330 Montevue Ln
20.00 USD
Nov
11
Twerk Fit Tuesdays
Nov 10, 2026 07:00 PM - 07:50 PM
6322 Windsor Mill Rd
23.18 USD - 104.23 USD
Nov
11
Unveiling Hidden Treasures with Arnold Lehman
Nov 11, 2026 06:30 PM - 08:00 PM
Washington County Museum of Fine Arts
10.10 USD - 12.23 USD
Nov
10
Needle Felting Workshop Cardinal Wreath
Nov 10, 2026 01:00 PM
Extraordinary Ewe 114 N Washington St Easton MD
Nov
10
Turkey/Snowman: Glen Burnie, Henny Macks with Artist Katie Detrich!
Nov 10, 2026 01:30 PM - 04:00 PM
Henny Macks Inn
USD 50
Nov
10
History Untapped: Faith, Foundation, and Forgotten Stories
Nov 10, 2026 02:00 PM
Vandiver Inn - Boutique Lodging & Events
Nov
11
Thanksgiving Bootcamp: Master the Feast. Lose the Stress
Nov 11, 2026 06:00 AM - 09:00 AM
No Thyme to Cook
Nov
11
Veterans Day at Queenstown Harbor
Nov 11, 2026 06:00 AM - 07:00 AM
310 Links Lane
Nov
12
410 Invitational - All Sessions
Nov 11, 2026 10:30 PM - Nov 12, 2026 12:30 AM
SECU Arena
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