Upcoming Events in Leonardtown

St. Mary’s Freedom Fest

 St. Mary’s Freedom Fest 3 Jul 2026
FREEDOM-FESTIVALS

Yung Joc LIVE at The Rex — It's Goin' Down in Leonardtown

 The Rex 2 May 2026
MUSIC USD 98 TO 535

Leprechaun Lilly's Kids Consignment Sale - 2026 Spring/Summer

 42455 Fairgrounds Rd, Leonardtown, MD, United States, Maryland 20650 16 Apr 2026
KIDS

RenFest Southern Maryland

 Brüdergarten (Brü) 23 May 2026
MUSIC USD 18 TO 50

29th Run & Fun Walk for Hospice of St. Mary’s

St. Mary's County Recreation & Parks 11 Apr 2026
NONPROFIT

Rabies Clinic with SMAWL @ St. Mary's Fair Grounds

 St. Mary's County Fairgrounds 11 May 2026
HEALTH-WELLNESS

LSM Night at The REX: The Evasons Mentalists & DJ Dance Party -- SPONSORS

 The Rex Theatre 11 Apr 2026
ENTERTAINMENT USD 0 TO 642

Rabies Clinic with SMAWL @ St. Mary's Fair Grounds

 St. Mary's County Fairgrounds 14 Sep 2026
HEALTH-WELLNESS

Rabies Clinic with SMAWL @ St. Mary's Fair Grounds

 St. Mary's County Fairgrounds 13 Apr 2026
HEALTH-WELLNESS

Leonardtown Wharf Coastal Arts Market

 Washington St, Leonardtown, MD 20650, United States 11 Apr 2026
ART

Spring Fling Open Market & Car Show

 Town Market LLC 26 Apr 2026
MUSIC

FREE! A "Good Earth" Day

 41675 Park Ave, Leonardtown, MD, United States, Maryland 20650 18 Apr 2026
KIDS

Rabies Clinic with SMAWL @ St. Mary's Fair Grounds

 St. Mary's County Fairgrounds 8 Jun 2026
DOG

Outdoor Art & Movie Night

 Town Market LLC 19 Sep 2026
ENTERTAINMENT

SOMD Wine in White: Studio 54 Edition | The Ultimate Disco Revival

 Olde Breton Inn 25 Jul 2026
PARTIES FREE

Cruisin’ Into Spring Break – Sun Cruiser DJ Night

 22695 Washington St, Leonardtown, MD, United States, Maryland 20650 4 Apr 2026
SPRING-BREAK

SMOKE SIGNALS & DJ PAPERS @ THE REX (LTOWN BAR CRAWL)

 The Rex 17 Apr 2026
PARTIES

Straight up party at Bru!

 Brudergarten Beer Garden at Shepherd’s Old Field Market 10 Apr 2026
PARTIES

My Third Eye — A TOOL Experience live at The Rex Theater

 The Rex Theatre 25 Apr 2026
ART

Momchella: Disco Cowgirl Day Party

 22695 Washington St, Leonardtown, MD, United States, Maryland 20650 16 May 2026
PARTIES

More things to do in Leonardtown

Food & Drinks
Festivals
Comedy
St. Patrick's Day
Fireworks
Easter Egg Hunt
Music Festivals
Bar Crawls
Pop-Ups