Leonardtown Events in September

Events in September in Leonardtown

Here’s your guide to all the happening concerts, festivals and events in September 2026 in Leonardtown. Catch the best of everything that your city has to offer here. Right from the flea market events to all the festivals; the September 2026 events in Leonardtown is all curated and sorted for you. Get going, buy your tickets and register to all the fun and exciting events already!

Events in September in Leonardtown

Sat, 12 Sep, 2026 - 11:00 AM

Vendors of Southern MD

Town Market LLC

30+ Interested
Tue, 08 Sep, 2026 - 09:00 AM

2026 Sultana Adult Paddling Experience-St. Mary's, MD

The Inn at Leonardtown, Ascend Hotel Collection

USD 1.6k
Sun, 27 Sep, 2026 - 12:00 PM

Fall Paw Crawl

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

33+ Interested
Sat, 05 Sep, 2026 - 05:00 PM

End of Summer Bash

Leonardtown Wharf
Sat, 05 Sep, 2026 - 09:00 AM

First Saturday of the Month Market Series

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

15+ Interested