Upcoming Leonardtown Events

Check out what's happening all around Leonardtown, MD

All Kinds of Minds : A Build-Your-Own Bullet Journal Workshop

 Sat, 03 Jan at 09:00 am 23140 Moakley St. Suite 6, Leonardtown, MD, United States, Maryland 20650

Easter Extravaganza

 Sat, 28 Mar at 09:00 am Town Market LLC 22675 Washington Street, The Bell Bldg Unit 106, Leonardown MD

Valentines' Day Sweets & Treats

Sat, 14 Feb at 09:30 am Town Market LLC

D&D Miniature Painting Contest

 Sat, 10 Jan at 01:00 pm Crafts N Stitches

January Jumpstart Weekend Sale

 Fri, 02 Jan at 10:00 am 22725 Duke St, Leonardtown, MD

Spring Fling Open Market & Car Show

 Sun, 26 Apr at 08:00 am 22675 Washington Street, The Bell Bldg, Leonardtown MD

Galentine's Sip & Shop Happy Hour

 Thu, 12 Feb at 06:00 pm 22695 Washington St, Leonardtown, MD, United States, Maryland 20650

Foreign Company at The Rex, Leonardtown MD

Sat, 31 Jan at 08:00 pm The Rex

DMATF@The Rex Leonardtown

 Sat, 24 Jan at 08:00 pm The Rex

Public Forum

 Tue, 13 Jan at 06:30 pm 41770 Baldridge Street, Leonardtown, MD, United States, Maryland 20650

Karaoke Open Mic Night | Actions Lounge & Billiards

 Sat, 03 Jan at 08:00 pm 25470 Point Lookout Rd, Leonardtown, MD 20650-3828, United States

Sip & Paint night Jan 2026

 Fri, 16 Jan at 06:15 pm 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

Mom's Day Out

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

Escape to the Tropics Party 🌴🐠

 Sat, 24 Jan at 06:00 pm 21935 Society Hill Rd, Leonardtown, MD

THE BASSMENT – A 7SOUNDSCAPE TAKEOVER

 Sat, 17 Jan at 08:00 pm The Rex Theatre

Meet & Greet at The Good Earth (meet new owner Abby & a farewell to current owner Valerie!)

 Fri, 02 Jan at 04:00 pm 41675 Park Ave, Leonardtown, MD, United States, Maryland 20650

Paint and Sip

 Fri, 16 Jan at 06:15 pm Port of Leonardtown Winery

Begin Where You Are: A Yoga Workshop

Wed, 07 Jan at 07:30 pm 23140 Moakley St. Suite 6, Leonardtown, MD, United States, Maryland 20650

Silent book club-SOMD Feb 2026

 Fri, 13 Feb at 08:30 pm Antoinette's Garden

COUSINS MAINE LOBSTER TRUCK AT PORT OF LEONARDTOWN WINERY

 Fri, 02 Jan at 12:00 pm Port of Leonardtown Winery

First BEACON Coalition Meeting

 Thu, 08 Jan at 06:00 pm 41680 Miss Bessie Dr., Ste 201, Leonardtown, MD, United States, Maryland 20650

🚨 WAKA FLOCKA FLAME LIVE at The Rex Theater! 🚨

 Thu, 22 Jan at 07:00 pm 22695 Washington St, Leonardtown, MD, United States, Maryland 20650

Nicotine Cessation Class - Standalone Sessions

 Wed, 07 Jan at 05:30 pm 21580 Peabody St, Leonardtown, MD, United States, Maryland 20650

The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours)

 Fri, 02 Jan at 10:00 am 41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650

Trivia Night @ The Rex!

Wed, 07 Jan at 06:00 pm 22695 Washington St, Leonardtown, MD

Beginner Plus Two Chunky Yarn Hand Kit Workshop

 Sun, 18 Jan at 01:00 pm Refined Beauty: Permanent Makeup & Lash Artistry

Breton Bay Community Event

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

January Meet & Greet

 Wed, 14 Jan at 05:30 pm Leonardtown Library

Welcome Back Wednesdays (weekly workshops) - January 2026

Wed, 07 Jan at 12:00 pm 22660 Washington St, Leonardtown, MD, United States, Maryland 20650

2026 Scholarship Fair

 Mon, 26 Jan at 05:00 pm Dr. James A. Forrest Career And Technology Center

Adult and Pediatric First Aid/CPR/AED Course

Thu, 29 Jan at 09:00 am 21580 Peabody St, Leonardtown, MD, United States, Maryland 20650

Stab & Gab - March 2026

 Sat, 14 Mar at 09:00 am Leonardtown Library

State of the Schools

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

Stab & Gab - Jan 2026

 Sat, 17 Jan at 09:00 am Leonardtown Library

Beat the Winter Blues and escape to the tropics with Mixtape (a Straight Vibin' Production)

 Sat, 24 Jan at 06:00 pm Breton Bay Golf & Country Club

Weekly Sound Reset

 Mon, 17 Nov at 06:00 pm 22660 Washington St USD 25 to 45