Upcoming Leonardtown Events

Check out what's happening all around Leonardtown, MD

Construction-Manufacturing-Transportation Job Fair

Thu, 20 Mar, 2025 at 10:00 am College of Southern Maryland, Leonardtown Campus Free

Construction-Manufacturing-Transportation Job Fair

 Thu, 20 Mar, 2025 at 10:00 am College of Southern Maryland, Leonardtown Campus Free

BLAZIN KEYS: DUELING PIANOS RETURNS!

Fri, 14 Mar, 2025 at 07:00 pm 22695 Washington St, Leonardtown, MD, United States, Maryland 20650

Southern Maryland Speakeasy

 Sat, 26 Jul, 2025 at 05:30 pm The Fenwick Inn

Battle by the Bay - Leonardtown, MD

 Sat, 12 Apr, 2025 at 05:00 pm 42455 Fairgrounds Rd, Leonardtown, MD 20650, United States

May 2nd GLASS BLOWING

 Fri, 02 May, 2025 at 12:30 pm 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

Mom's Day Out

 Sat, 10 May, 2025 at 09:00 am Town Market LLC

March Pi Day Full Moon/Eclipse Soundbath

 Fri, 14 Mar, 2025 at 06:00 pm 22525 Washington Street , Leonardtown, MD, United States, Maryland 20650

Cousins Maine Lobster at Port of Leonardtown Winery

 Sun, 23 Feb, 2025 at 12:00 pm 23190 Newtowne Neck Rd, Leonardtown, MD 20650

LSM Night at The REX feat. Unfinished Business

 Fri, 04 Apr, 2025 at 07:00 pm The Rex Theatre USD 18

Mini Sign Workshops 💛 Kid Friendly Ages 6+!

 Sat, 08 Mar, 2025 at 01:00 pm 41665 Fenwick Street, Unit 15, Leonardtown, MD 20650

The Rex Theatre

 Sat, 29 Mar, 2025 at 07:00 pm The Rex Theatre

March Mats & Mimosas Workshop! 🎨 DIY Custom Doormat

 Sat, 22 Mar, 2025 at 01:00 pm 41665 Fenwick Street, Unit 15, Leonardtown, MD, United States, Maryland 20650

Levi Stephens LIVE

 Fri, 07 Mar, 2025 at 05:00 pm 22845 Washington Street. Unit C, Leonardtown, MD

The Addams Family Musical

Thu, 13 Mar, 2025 at 07:00 pm 22600 Camp Calvert Rd, Leonardtown, MD 20650-4705, United States

TRAPT: Full Band Acoustic Show

Sat, 26 Apr, 2025 at 08:00 pm 22695 Washington St, Leonardtown, MD, United States, Maryland 20650

Swing Away at the Port of Leonardtown

 Sat, 01 Mar, 2025 at 02:00 pm Port of Leonardtown Winery

SMCYO Pre-Season Fielding Clinic 2

 Sun, 02 Mar, 2025 at 01:00 pm Leonard Hall Rec Center

LCotN Women's Luncheon

 Sat, 15 Mar, 2025 at 11:00 am 22730 Washington St, Leonardtown, MD, United States, Maryland 20650

SMCYO Pre-Season Fielding Clinic 1

 Sun, 23 Feb, 2025 at 01:00 pm Leonard Hall Rec Center

Public Domain Mardi Gras Party

 Sat, 01 Mar, 2025 at 09:00 pm Brudergarten Beer Garden at Shepherd’s Old Field Market

Ally Venable: Money & Power Tour

 Sat, 10 May, 2025 at 08:00 pm 22695 Washington St, Leonardtown, MD, United States, Maryland 20650

Retro Arcade Every Sunday!

Sun, 23 Feb, 2025 at 01:00 pm 22695 Washington St, Leonardtown, MD

Southside Business Social: Putting Your Vision into Action!

 Wed, 05 Mar, 2025 at 03:00 pm Social on Fenwick Free

28th Annual Hospice Run/Walk

 Sat, 05 Apr, 2025 at 08:30 am 23110 Leonard Hall Dr, Leonardtown, MD 20650-5831, United States

Kentucky Derby Watch Party and Raffle

 Sat, 03 May, 2025 at 05:00 pm Bowles Farm

International Dance Day Celebration 2025

 Sat, 26 Apr, 2025 at 06:30 pm Leonardtown Town Square Free

Adult Prom Night!

Sat, 17 May, 2025 at 08:00 pm 22695 Washington St, Leonardtown, MD

April Mats & Mimosas Workshop! 🎨 DIY Custom Doormat

 Sat, 19 Apr, 2025 at 01:00 pm 41665 Fenwick Street, Unit 15, Leonardtown, MD, United States, Maryland 20650

Wine In White 2025: SoMD Speakeasy

 Sat, 26 Jul, 2025 at 05:30 pm The Fenwick Inn USD 82

Easter Extravaganza

 Sat, 12 Apr, 2025 at 09:00 am Town Market LLC

Sweet Wine of Mine Tasting Event

 Sun, 23 Feb, 2025 at 02:00 pm The Inn at Leonardtown, Ascend Hotel Collection

Let's Design a Native Garden

 Sat, 15 Mar, 2025 at 09:30 am St. Mary's County Library (Leonardtown Library)

2025 Second Friday Socials at SMC Arts Council

 Fri, 14 Mar, 2025 at 01:00 pm 22660 Washington St., Leonardtown, MD, United States, Maryland 20650

Young Professionals Networking Event at SIP Cafe & Lounge Leonardtown (FREE!)

 Tue, 18 Mar, 2025 at 05:00 pm SIP Ltown

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

 Fri, 07 Mar, 2025 at 10:00 am 41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650

St Patrick's Day Charcuterie Class

 Thu, 13 Mar, 2025 at 06:15 pm 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

State of the Schools

Thu, 27 Feb, 2025 at 11:00 am Forrest Technology Center 24005 Point Lookout Road Leonardtown, MD 20650

Neighborhood Nail Trim Day- Clark’s Rest and Leonard’s Grant

 Tue, 25 Feb, 2025 at 03:00 pm Leonard's Grant Leonardtown, MD

Moll Dyer Rock Sundae

 Fri, 21 Feb, 2025 at 01:00 pm The Salted Scoop

MCA Car Show

 Sat, 03 May, 2025 at 08:00 am Mother Catherine Academy

SAVE THE DATE: Summer Camp Registration

 Mon, 03 Mar, 2025 at 09:00 am St. Mary's County Recreation & Parks

Free Admission for Military on Armed Forces Day at the St. Mary's County Museums

 Sat, 17 May, 2025 at 10:00 am St. Mary's County, Maryland

60th East Coast Shotokan karate Association Championships

 Sat, 03 May, 2025 at 09:00 am Leonardtown High School

St. Mary's County History Day

 Sat, 08 Mar, 2025 at 09:00 am Leonardtown Library - St. Mary's County Library Free

The Red Jumpsuit Apparatus @ The Rex in Leonardtown

 Sat, 15 Mar, 2025 at 07:00 pm The Rex

Free Admission for Moms on Mother's Day at St. Mary's County Museums

 Sun, 11 May, 2025 at 10:00 am St. Mary's County, Maryland
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