Leonardtown Parties Events

Summer Smash 2.0

The Rex 8 Aug 2026

SMBC Boat Regatta the Wharf

Leonardtown Wharf 25 Jul 2026

Monster Mash Bash

Leonardtown Wharf 24 Oct 2026

Outdoor Art & Movie Night

Town Market LLC 19 Sep 2026

The Joe Cox Band LIVE @ The Rex Theatre

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 29 Aug 2026

Christmas In July @ The Rex Theater 🎄

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 25 Jul 2026

Friday Summer Skate

Leonard Hall Rec Center 17 Jul 2026

Smoke-Fire-Fore! ALVFD Golf Tournament

Breton Bay Golf & Country Club 31 Jul 2026

Trunk or Treat & Vendor Show

Town Market LLC 24 Oct 2026

Paws & Popcorn Movie Night: Alice in Wonderland (live action)

Meow Dyer Cat Cafe, LLC 17 Jul 2026

Heroes on the Water, Maryland Chapter - Kayak Fishing at Saint Mary's Lake

Saint Marys River State Park 8 Aug 2026

End of Summer Bash

Leonardtown Wharf 5 Sep 2026

Retail Launch!

22695 Washington Street, Leonardtown, MD 16 Jul 2026

The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours) (FREE)

41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650 4 Sep 2026

Holiday Market with The Grinch & Cindy Lou Who

Town Market LLC 27 Nov 2026

Fall Paw Crawl

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650 27 Sep 2026

Diamonds in the Rough

21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 25 Jun 2026

First Saturday of the Month Market Series

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 1 Aug 2026

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 4 Oct 2026

Pages in the Park

Port of Leonardtown Park & Kayak Launch 4 Oct 2026

Storytime in the Park

Port of Leonardtown Park & Kayak Launch 17 Oct 2026

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 20 Sep 2026

Watercolor Blooms Painting Party Hosted by Brandy Blackstone

22694 Washington St 11 Aug 2026

Pages in the Park

23190 Newtowne Neck Rd, Leonardtown, MD 20650, United States 3 Oct 2026

Team Trivia at The Bay!

21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 16 Jul 2026

Stab & Gab - August 2026

Leonardtown Library 29 Aug 2026

Alrissa Tobe & Chris Clayton Wedding Shower

22730 Washington St, Leonardtown, MD, United States, Maryland 20650 18 Jul 2026