Upcoming Events in Leonardtown

Halloween 2026 @ Cryer's Back Road Inn

01 November 2026

Compton, MD

Back Road Inn, 22094 Newtowne Neck Rd

Stab & Gab - Jan 2026

17 January 2026

Leonardtown, MD

Leonardtown Library - St. Mary's County Library, 23630 Hayden Farm Ln

Small Business Saturday at St. Mar'y's County Arts

29 November 2025

Leonardtown, MD

St. Mary's County Arts Council, 22660 Washington St

Public Forum

04 November 2025

Leonardtown, MD

41770 Baldridge St

Spring Book Sale

25 April 2026

Leonardtown, MD

St. Mary's County Fair Association Inc., 42455 Fairgrounds Rd

Spring Book Sale (Members-Only Day)

24 April 2026

Leonardtown, MD

St. Mary's County Fair Association Inc., 42455 Fairgrounds Rd

Tinsel & Tape: Holiday Wrapping Workshop

11 December 2025

Leonardtown, MD

The Fenwick Inn, 41685 Fenwick St

Harry Potter Mystic Market & First Saturday of the

01 November 2025

Leonardtown, MD

MedStar St Mary's Hospital, 25500 Point Lookout Rd

Vendors of Southern MD

12 September 2026

Leonardtown, MD

Town Market LLC, The Bell Building, 22675 Washington St Unit 106

Holiday Gratitude: Chair Dance for Mind-Body Wellness

11 December 2025

Leonardtown, MD

Garvey Senior Activity Center, 23630 Hayden Farm Ln