Leonardtown Parties Events

St. Mary’s Freedom Fest

St. Mary’s Freedom Fest 3 Jul 2026

SUMMER SMASH

The Rex 20 Jun 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

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 26 Jun 2026

Trunk or Treat & Vendor Show

Town Market LLC 24 Oct 2026

Cocktail Party and Fundraiser with Chuck!

Port of Leonardtown Winery 27 Jun 2026

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

Saint Marys River State Park 8 Aug 2026

🌴 Tropic Like It’s Hot: Ladies Night Sip & Shop

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

🎉 YOU’RE INVITED… THE SALON TURNS 1! 🐾💜

22725 Duke Street 11 Jul 2026

Jacob & Friends Fundraising Cabaret

The Rex 25 Jun 2026

Holiday Market with The Grinch & Cindy Lou Who

Town Market LLC 27 Nov 2026

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 28 Jun 2026

End of Summer Bash

Leonardtown Wharf 5 Sep 2026

Fall Paw Crawl

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

Slumber party Silent reading party

Antoinette’s Garden 23 Jun 2026

First Saturday of the Month Market Series

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

Storytime in the Park

Port of Leonardtown Park & Kayak Launch 17 Oct 2026

Pages in the Park

Port of Leonardtown Park & Kayak Launch 4 Oct 2026

Karaoke Night | Actions Lounge & Billiards

25470 Point Lookout Rd, Leonardtown, MD 20650-3828, United States 20 Jun 2026

Stab & Gab - August 2026

Leonardtown Library 29 Aug 2026