Upcoming Leonardtown Events

Check out what's happening all around Leonardtown, MD

Vendors of Southern MD

 Sat, 20 Sep at 10:00 am Town Market LLC

Outdoor Movie Night in LTown Alley

 Fri, 26 Sep at 07:30 pm LTown Alley (Alice in LTown Mural) - 41676 Park Ave, Leonardtown, MD 20650, United States

Blessing of the Fleet 2025

 Sat, 04 Oct at 12:00 pm Leonardtown Wharf

Cars & Coffee Car Show

 Sun, 24 Aug at 10:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD

SMAWL Vaccination Clinic

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

Saturday Night DJ CJ @Action

Sat, 16 Aug at 09:30 pm 25470 Point Lookout RD, Leonardtown, MD

Small Business Saturday with The Grinch & Cindy Lou Who

 Sat, 29 Nov at 09:00 am Town Market LLC

Throwback Party!

 Sat, 23 Aug at 08:00 pm 41655 Fenwick St, Leonardtown, MD

Sidewalk Art Showcase

 Sun, 07 Sep at 10:00 am Leonardtown Wharf

Free Concert on the Lawn featuring Unfinished Business

 Fri, 22 Aug at 06:00 pm 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650

8 Ball Scotch Doubles Pool Tournament

 Sat, 16 Aug at 12:00 pm Action Lounge and Billiards

First Saturday of the Month Market Series

 Sat, 01 Nov at 09:00 am 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

SPORT CARD VENDOR DAY @ THE REX

 Sat, 23 Aug at 12:00 pm The Rex

First Saturday of the Month Market Series

 Sat, 06 Dec at 09:00 am 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

Face Painting by Azul - September First Friday

 Fri, 05 Sep at 05:00 pm 22660 Washington St., Leonardtown, MD, United States, Maryland 20650

August 29th Glass Blowing w/McFadden Art Glass

 Fri, 29 Aug at 11:30 am 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

Fleetwood Mac/Stevie Nicks Tribute at The Rex

 Fri, 05 Sep at 07:00 pm The Rex

Dungeons and Drafts

 Tue, 19 Aug at 06:00 pm 22725 Duke St, Leonardtown, MD 20650-4165, United States

2025 First Friday Drumline Events!

 Fri, 03 Oct at 05:30 pm 22660 Washington St., Leonardtown, MD, United States, Maryland 20650

TSC Acoustic Live at the Planetarium!

Fri, 03 Oct at 07:00 pm STARS To STEM, Inc.

Mystic Dead Quartet at the Planetarium

 Fri, 24 Oct at 06:30 pm STARS To STEM, Inc.

Clements Cuties Foundation Benefit 8 Ball Tournament!

 Sat, 16 Aug at 12:00 pm 25470 Point Lookout RD, Leonardtown, MD

Annual Antique Tractor & Truck Parade

 Sun, 05 Oct at 01:00 pm Town of Leonardtown

Death at the Disco

 Sun, 19 Oct at 06:00 pm Antoinette’s Garden USD 20

Live at Port of Leonardtown Winery

 Sat, 23 Aug at 02:00 pm Port of Leonardtown Winery

Hot Ice Live @ Port Of Leonardtown Winery

 Sat, 06 Sep at 02:00 pm Port of Leonardtown Winery

PADI Open Water Scuba Diver Course

 Sat, 16 Aug at 12:00 pm Csm Leonardtown Campus

Levi Stephens LIVE

 Sat, 18 Oct at 05:00 pm 22845 Washington Street. Unit C, Leonardtown, MD

Winery Pop-Up

 Fri, 05 Sep at 01:00 pm Port of Leonardtown Park & Kayak Launch

Negotiating Changing Chesapeake Identities:

 Wed, 20 Aug at 07:00 pm The Inn at Leonardtown

Wine & Whiff

 Sat, 16 Aug at 05:30 pm 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650

September Glass Blowing w/ McFadden glass

 Fri, 05 Sep at 12:30 pm 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

First Saturday of the Month Market Series

 Sat, 06 Sep at 09:00 am 22675 Washington St, The Bell Bldg Unit 106, Leonardtown, MD 20650-3848, United States

Spin It Again at Blessing of the Fleet

 Sat, 04 Oct at 12:00 pm Leonardtown Wharf Park

Season Ending Diamonds in the Rough

 Tue, 19 Aug at 05:30 pm 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650

Puppet Show in the Park

 Sat, 20 Sep at 11:00 am Port of Leonardtown Park & Kayak Launch

2025 Audience Participation Drum Circle Events

 Fri, 05 Sep at 05:00 pm St. Mary's County Arts Council

Pilates & Mimosas morning

 Sat, 23 Aug at 10:00 am 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

Sunday Funday @ Action

 Sun, 17 Aug at 12:00 pm 25470 Point Lookout RD, Leonardtown, MD

Sabbath @ The Rex !

 Sat, 08 Nov at 07:00 pm The Rex

Warfighter Advance Auction & Gala

 Sat, 23 Aug at 06:00 pm Olde Breton Inn and Bailey's Catering

For the first time ever!!!

Thu, 18 Sep at 07:00 pm The Rex

LHS Class of 2015 Reunion

 Sat, 13 Sep at 06:00 pm Port of Leonardtown Winery

Celebrating 1 Year of Care, Community, and Connection

 Fri, 19 Sep at 05:00 pm 25482 Point Lookout Rd Unit #201, Leonardtown, MD, United States, Maryland 20650

Monster Mash Bash

 Sun, 19 Oct at 01:00 pm Leonardtown Wharf

Midnight Sunsets at The Rex

Thu, 21 Aug at 07:00 pm The Rex Theatre

4th Annual Walk for Recovery

Sat, 20 Sep at 09:00 am Leonardtown Square

First Saturday of the Month Market Series

 Sat, 04 Oct at 09:00 am 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

Fall Craft and Vendor Sale and Community Yard Sale

 Sat, 27 Sep at 07:00 am St. Mary's County Fairgrounds

Death at the Speakeasy

 Tue, 26 Aug at 06:00 pm Antoinette’s Garden USD 15

Hello Brunchy

 Sat, 23 Aug at 12:00 pm Botanic Cafe-Delicatessen

Faire Witch Project at The Rex Theatre

 Thu, 02 Oct at 06:00 pm 22695 Washington St, Leonardtown, MD

PAINT Rocks for September First Friday

 Fri, 05 Sep at 04:30 pm rm. 204 22660 Washington Street, Leonardtown, MD, United States, Maryland 20650

Josh Airhart Solo @ POL Winery

 Sat, 16 Aug at 02:00 pm Port of Leonardtown Winery

ALL-YOU-CAN-EAT SPAGHETTI SUNDAYS AT LEDO PIZZA!

 Sun, 17 Aug at 11:00 am 25460 Point Lookout Road, Leonardtown, MD 20650

Native Plant and Seed Swap and Share

 Sat, 04 Oct at 10:00 am St. Mary's County Library

2025 Second Friday Socials at SMC Arts Council

 Fri, 12 Sep at 01:00 pm 22660 Washington St., Leonardtown, MD, United States, Maryland 20650

Adult and Pediatric First Aid/CPR/AED Course

Thu, 25 Sep at 09:00 am 21580 Peabody St, Leonardtown, MD, United States, Maryland 20650

Paranoid Gremlin Art Time 🌈

 Sat, 20 Sep at 01:00 pm Town of Leonardtown

The Local Lemon at SPICE

 Fri, 29 Aug at 09:30 am 22725 Washington Street, Leonardtown, MD, United States, Maryland 20650

Leprechaun Lilly's Kids Consignment Sale - 2025 Fall/Winter

 Thu, 09 Oct at 04:00 pm 42455 Fairgrounds Rd, Leonardtown, MD, United States, Maryland 20650

Chesapeake Mermaid at U.S. Oyster Festival

 Sat, 18 Oct at 12:00 pm St. Mary's County Fairgrounds

The Fenwick Inn presents a Mad Hatter's Tea

 Sun, 28 Sep at 12:30 pm The Fenwick Inn USD 50 to 71

Cars & Coffee Car Show

 Sun, 07 Sep at 10:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD

Feud Trivia Night

 Tue, 19 Aug at 06:30 pm 41655 Fenwick St, Leonardtown, MD

Nicotine Cessation Class - Standalone Sessions

 Wed, 10 Sep at 05:30 pm 21580 Peabody St, Leonardtown, MD, United States, Maryland 20650

Leonardtown Local Author & Book Fair

 Sun, 14 Sep at 10:00 am The Rex

SMAWL Vaccination Clinic

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

US Oyster Festival

 Sat, 18 Oct at 10:00 am St. Mary's County Fairgrounds USD 5 to 24

Trunk or Treat & Vendor Show

 Sat, 25 Oct at 09:00 am Town Market LLC

September Leonardtown Business Association Meeting

Fri, 12 Sep at 08:15 am Leonardtown Town Hall

Cars & Coffee Car Show

 Sun, 05 Oct at 10:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD

Adult and Pediatric First Aid/CPR/AED Course

Thu, 13 Nov at 09:00 am 21580 Peabody St, Leonardtown, MD, United States, Maryland 20650

FAW Crusader Cup Tournament 2025

 Fri, 17 Oct at 09:00 am Breton Bay Golf & Country Club

28 Sept Kelly McGinn Clinic

Sun, 28 Sep at 09:00 am 41345 Camp Maria Rd, Leonardtown, MD 20650-4220, United States, Leonardtown, MD

SMAWL Vaccination Clinic

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

(Friday event} Salsa On The Vine at The Port of Leonardtown Winery.

 Fri, 19 Sep at 06:00 pm Port of Leonardtown Winery

October Leonardtown Business Association Meeting

Fri, 10 Oct at 08:15 am Leonardtown Town Hall

Public Forum

 Tue, 04 Nov at 06:30 pm 41770 Baldridge Street, Leonardtown, MD, United States, Maryland 20650

Veteran's Day Celebration

 Tue, 11 Nov at 09:00 am Town Market LLC

Cars & Coffee Car Show

 Sun, 21 Sep at 10:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD

Cars & Coffee Car Show

 Sun, 19 Oct at 10:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD

Stab & Gab - August 2025

 Sat, 16 Aug at 09:00 am Leonardtown Library

Historically Speaking: Negotiating Changing Chesapeake Identities

 Wed, 20 Aug at 07:00 pm The Inn at Leonardtown

Stab & Gab - October 2025

 Sat, 18 Oct at 09:00 am Leonardtown Library

Southern Maryland Planning Community Meeting

Wed, 15 Oct at 09:00 am 23630 Hayden Farm Ln, Leonardtown, MD 20650-5888, United States

Fur Babies with the Grinch and Holiday Market

 Sat, 06 Dec at 09:00 am 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

Cars & Coffee Car Show

 Sun, 19 Oct at 05:00 am 22675 MD-326, Leonardtown, MD 20650-3848, United States

Mechanicsville Braves 5th Annual Golf Tournament

Thu, 23 Oct at 08:00 am Breton Bay Golf & Country Club

Stab & Gab - Sept 2025

 Sat, 06 Sep at 09:00 am Leonardtown Library

Come Out and See the Grinch & Christmas Shopping Spree

 Sat, 13 Dec at 09:00 am Town Market LLC

Fall Dinner

 Fri, 24 Oct at 06:00 pm Olde Breton Inn

Pictures with Santa Clause

Sat, 20 Dec at 09:00 am Town Market LLC

Holiday Market with The Grinch & Cindy Lou Who

 Fri, 28 Nov at 09:00 am Town Market LLC

Awesome Scavenger Hunt! - Leonardtown Loot & Legends Hunt

 Wed, 04 Dec at 08:00 am 41680 Tudor Pl USD 15

Sunset Cruise @ Leonardtown Wharf

 Fri, 30 May at 06:15 pm Leonardtown Wharf
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