Leonardtown Events

Explore Leonardtown, Maryland, through its vibrant calendar of events, offering something for everyone year-round. From lively festivals and farmers' markets to art exhibits and community gatherings, this charming town invites you to experience its rich culture and friendly atmosphere. Stay up-to-date and plan your visit to join in the fun!

May 2026

Momchella: Disco Cowgirl Day Party
May 16, 2026

Uncorked & Unveiled: Island Edition
May 21, 2026

June 2026

First Responder First Friday Weekend
June 5 - 7, 2026

First Saturday Market Series - June
June 6, 2026

40th Annual Crab and Music Festival
June 13, 2026

July 2026

St. Mary's Freedom Fest
July 3, 2026

Red, White & Blues First Friday Weekend
July 3 - 5, 2026

First Saturday Market Series - July
July 4, 2026

August 2026

First Saturday Market Series - August
August 1, 2026

Sizzling Summer First Friday Weekend
August 7 - 9, 2026

September 2026

ArtWalk First Friday Weekend
September 4 - 6, 2026

First Saturday Market Series - September
September 5, 2026

Paw Crawl
September 27, 2026

October 2026

Octoberfest First Friday Weekend
October 2 - 4, 2026

First Saturday Market Series - October
October 3, 2026

Scarecrow Stroll
October 3 - 31, 2026

November 2026

Passport to the Holidays
November 6, 2026

First Saturday Market Series - November
November 7, 2026

December 2026

Gingerbread Lane
December 4, 2026

First Saturday Market Series - December
December 5, 2026

Past Events

First Saturday Market Series - May
May 2, 2026

Vintage Vibes May First Friday
May 1 - 3, 2026

Southern Maryland Spring Festival
April 30, 2026 to May 3, 2026

Spring Fling Car Show
April 26, 2026

Newtowne Manor Walk in the Park
April 25, 2026

Paws and Popcorn Night
April 24, 2026

Spring Book Sale
April 24 - 26, 2026

Sip and Swap: Ladies Night
April 23, 2026

Cultivate and Create Plant Class
April 22, 2026

Ride the Waves of Acceptance
April 18, 2026

Cherry Blossom Sip and Paint Night
April 18, 2026

Barmuda Triangle Spring Bar Crawl
April 17, 2026

August First Friday in Leonardtown
August 1 - 3, 2025

Southern Maryland Boat Club Summer Boat Regatta
July 26 - 27, 2025

July First Friday in Leonardtown
July 4 - 6, 2025

Annual St. Mary's County Crab Festival
June 14, 2025

June First Friday in Leonardtown
June 6 - 8, 2025

RenFest Southern Maryland
May 24 - 25, 2025

Leonardtown Summer Splash Silent Disco
May 23, 2025

Southern Maryland Heritage Festival
May 17 - 18, 2025