Upcoming Leonardtown Events

Check out what's happening all around Leonardtown, MD

St. Mary’s Freedom Fest

 Fri, 03 Jul at 08:00 pm St. Mary’s Freedom Fest

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

 Sat, 02 May at 07:00 pm The Rex USD 98 to 535

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

 Thu, 16 Apr at 04:00 pm 42455 Fairgrounds Rd, Leonardtown, MD, United States, Maryland 20650

RenFest Southern Maryland

 Sat, 23 May at 10:00 am Brüdergarten (Brü) USD 18 to 50

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

Sat, 11 Apr at 08:30 am St. Mary's County Recreation & Parks

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

 Mon, 11 May at 06:00 pm St. Mary's County Fairgrounds

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

 Sat, 11 Apr at 08:00 pm The Rex Theatre USD 0 to 642

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

 Mon, 14 Sep at 06:00 pm St. Mary's County Fairgrounds

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

 Mon, 13 Apr at 06:00 pm St. Mary's County Fairgrounds

Leonardtown Wharf Coastal Arts Market

 Sat, 11 Apr at 09:00 am Washington St, Leonardtown, MD 20650, United States

Spring Fling Open Market & Car Show

 Sun, 26 Apr at 07:00 am Town Market LLC

FREE! A "Good Earth" Day

 Sat, 18 Apr at 10:00 am 41675 Park Ave, Leonardtown, MD, United States, Maryland 20650

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

 Mon, 08 Jun at 06:00 pm St. Mary's County Fairgrounds

Outdoor Art & Movie Night

 Sat, 19 Sep at 03:00 pm Town Market LLC

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

 Sat, 25 Jul at 05:30 pm Olde Breton Inn Free

Cruisin’ Into Spring Break – Sun Cruiser DJ Night

 Sat, 04 Apr at 09:00 pm 22695 Washington St, Leonardtown, MD, United States, Maryland 20650

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

 Fri, 17 Apr at 09:00 pm The Rex

Straight up party at Bru!

 Fri, 10 Apr at 07:00 pm Brudergarten Beer Garden at Shepherd’s Old Field Market

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

 Sat, 25 Apr at 07:00 pm The Rex Theatre

Momchella: Disco Cowgirl Day Party

 Sat, 16 May at 12:00 pm 22695 Washington St, Leonardtown, MD, United States, Maryland 20650

Infinity Day Celebration

 Sat, 08 Aug at 09:30 am Port of Leonardtown Park & Kayak Launch

Battle by the Bay - Leonardtown, MD

 Sat, 11 Apr at 05:00 pm 42455 Fairgrounds Rd, Leonardtown, MD 20650, United States

🌎♻️ SIP & SWAP – Ladies Night at The Rex

 Thu, 23 Apr at 06:00 pm 22695 Washington St, Leonardtown, MD, United States, Maryland 20650

Pet Parents Day: Adopt.Tattoo.Repeat.

 Sun, 26 Apr at 11:00 am Shepherd's Old Field Market

FOL Annual Spring BOOK Sale 2026

 Fri, 24 Apr at 12:00 pm 42455 Fairgrounds Rd., Leonardtown, MD, United States, Maryland 20650

April Showers☔️: Pet Wash Fundraiser 🐶🛁

 Sat, 18 Apr at 12:00 pm 22725 Duke St, Leonardtown, MD 20650-4165, United States

Vendors of Southern MD

 Sat, 12 Sep at 11:00 am Town Market LLC

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

 Tue, 08 Sep at 09:00 am The Inn at Leonardtown, Ascend Hotel Collection USD 1,592 to 1,800

End of Summer Bash

Sat, 05 Sep at 05:00 pm Leonardtown Wharf

St. Mary's County History Day

 Sat, 18 Apr at 09:00 am Leonardtown Library - St. Mary's County Library Free

SMAWL Low Cost Vaccination Clinic

Mon, 10 Aug at 06:00 pm St. Mary's County Fairgrounds

Mom's Day Out

 Sat, 09 May at 09:30 am Town Market LLC

Fall Paw Crawl

 Sun, 27 Sep at 12:00 pm 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650

Storytime in the Park

 Sat, 09 May at 09:30 am Port of Leonardtown Park & Kayak Launch

First Saturday of the Month Market Series

 Sat, 04 Apr 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

2026 Annual St John’s School Golf Tournament

 Thu, 07 May at 08:00 am Breton Bay Golf & Country Club

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

 Sat, 08 Aug at 07:00 am Saint Marys River State Park Free

Vintage Yard Sale

 Sat, 02 May at 09:30 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650

Spring Fling Open Market & Car Show

 Sat, 25 Apr at 04:00 am 22675 MD-326, Leonardtown, MD 20650-3848, United States

State of the Schools

Tue, 28 Apr at 11:00 am Dr. James A. Forrest Career And Technology Center

Art and Craft popup Show

 Fri, 24 Apr at 08:00 am Leonard Hall Recreation Center Free

Breton Bay Community Event

 Fri, 15 May at 06:00 pm Breton Bay Dr, Leonardtown, MD 20650, United States

Community Shred & Medication Take Back

 Sat, 25 Apr at 09:00 am 41780 Baldridge Street, Leonardtown, MD, United States, Maryland 20650

Stab & Gab - April 2026

 Sat, 04 Apr at 09:00 am Leonardtown Library

Stab & Gab - June 2026

 Sat, 20 Jun at 09:00 am Leonardtown Library

Public Hearing: FY2027 Recommended County Budget

 Tue, 21 Apr at 06:30 pm Leonardtown High School

Spring Cleaning Sale

Sat, 25 Apr at 09:00 am 41695 Fenwick Street, Leonardtown, MD

Stab & Gab @ Social Coffee

 Sat, 02 May at 09:00 am Social Coffeehouse

Mom's Day Out Flower Workshop

 Sat, 09 May at 04:00 am 22675 MD-326, Leonardtown, MD 20650-3848, United States