Upcoming Leonardtown Events

Check out what's happening all around Leonardtown, MD

Afternoon Tea - Vegan Edition

 Sun Oct 06 2024 at 10:00 am Port of Leonardtown Winery USD 74

SMAR YPN Oktoberfest Networking Event

 Thu Oct 03 2024 at 05:00 pm Brüdergarten (Brü) Free

First Friday Meet & Greet - David W. Cook, Tenor

 Fri Oct 04 2024 at 05:30 pm 22660 Washington St., Leonardtown, MD, United States, Maryland 20650

Tea Party at POL Winery

 Sun Oct 06 2024 at 10:00 am Port of Leonardtown Winery

October Make & Take 🎃 Make your own Pumpkin Patch!

 Sat Oct 05 2024 at 09:30 am 41665 Fenwick Street, Unit 15, Leonardtown, MD, United States, Maryland 20650

Halloween Movie Festival

 Sat Oct 26 2024 at 04:00 pm Leonardtown Wharf

Unstoppable You Safety and Self-defense Workshop (Southern Maryland)

 Sat Oct 26 2024 at 10:00 am Leonardtown Library - St. Mary's County Library Free

Decades Night

 Fri Oct 18 2024 at 08:00 pm The Rex Theatre

CrafterParty Broom Making Workshop at The Fenwick Inn

 Thu Oct 10 2024 at 06:30 pm The Fenwick Inn

Howl-oween Pawty

 Sat Oct 26 2024 at 11:00 am EarthWise Pet Leonardtown

Bus Trip to New York City

 Sat Dec 14 2024 at 06:30 am 23150 Leonard Hall Dr, Leonardtown, MD, United States, Maryland 20650

ALVFD Shuffle Bowl Tournament

 Sat Nov 02 2024 at 12:00 pm Cryer's Back Road Inn

Christmas on the Square & Annual Tree Lighting

 Fri Nov 29 2024 at 05:30 pm Town of Leonardtown

2024 Leonardtown Square Fall Bar Crawl

 Sat Oct 12 2024 at 12:00 pm Leonardtown Square

First Friday Audience Participation Drum Circle-October 2024

 Fri Oct 04 2024 at 05:00 pm St. Mary's County Arts Council

90-Minute Small Fitness Ball Workshop

 Thu Oct 03 2024 at 06:30 pm Method Gym Leonardtown, MD

All the Dirt on Collecting Native Plant Seeds

 Sat Oct 12 2024 at 02:00 pm St. Mary's County Library (Leonardtown Library)

CrafterParty Broom Making Workshop at The Fenwick Inn

 Thu Oct 10 2024 at 06:30 pm The Fenwick Inn USD 55

14th Annual SOMD Antique Power Parade

 Sun Oct 06 2024 at 01:00 pm Leonardtown Square

OES PTA Spirit Night at Slice House

 Thu Oct 17 2024 at 03:00 pm The Slice House

Chesapeake Mermaid at 58th Annual US Oyster Festival

 Sat Oct 19 2024 at 12:00 pm St. Mary's County Fairgrounds

Annual Antique Tractor & Truck Parade

 Sun Oct 06 2024 at 01:00 pm Town of Leonardtown

2024 First Friday Drumline Performances

 Fri Oct 04 2024 at 05:30 pm 22660 Washington St., Leonardtown, MD, United States, Maryland 20650

SJS Spirit Night

 Tue Oct 22 2024 at 04:00 pm Ledo Pizza (Leonardtown)

St. Mary's Ryken Golf Classic

 Fri Oct 04 2024 at 08:00 am Breton Bay Golf & Country Club

Bus Trip to Ocean City

 Sat Oct 26 2024 at 07:00 am 23150 Leonard Hall Dr, Leonardtown, MD, United States, Maryland 20650

First Saturday of the Month Market Series

 Sat Oct 05 2024 at 08:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650

FALL CRAFT & VENDOR SHOW

 Sat Oct 05 2024 at 08:00 am St. Mary's County Fairgrounds

Leprechaun Lilly's Kids Consignment Sale - 2024 Fall/Winter

 Fri Oct 11 2024 at 09:00 am 42455 Fairgrounds Rd, Leonardtown, MD, United States, Maryland 20650

Fall paint night w/ Salty Paintz

 Wed Oct 09 2024 at 06:00 pm 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

ALVFD Fall Craft & Vendor Show

 Sat Oct 26 2024 at 09:00 am Leonardtown Volunteer Fire Department

Coffee Time with Dee

 Wed Oct 02 2024 at 07:00 am Social Coffeehouse

FALL YARD SALE

 Sat Oct 05 2024 at 07:00 am St. Mary's County Fairgrounds

LCotN Yard Sale

 Sat Oct 12 2024 at 08:00 am 22730 Washington St, Leonardtown, MD, United States, Maryland 20650

Harvest Festival

 Sat Oct 12 2024 at 11:00 am EarthWise Pet Leonardtown

2024 Public Forums

Tue Oct 29 2024 at 06:30 pm Chesapeake Building

Class of 2014 Reunion

 Fri Oct 18 2024 at 05:00 pm St. Mary's Ryken High School

Witches & Wine

 Tue Oct 01 2024 at 06:00 pm Antoinette’s Garden USD 13

Red Dirt Revolution at The Rex (MD)

 Fri Oct 11 2024 at 08:00 pm The Rex

Veteran's Day Celebration

 Mon Nov 11 2024 at 10:00 am Town Market LLC

12th Annual Camp Maria Oyster Scald Sponsored by J.F. Taylor, Inc.

 Sun Oct 13 2024 at 12:00 pm 41290 Camp Maria Rd, Leonardtown, MD, United States, Maryland 20650

First Saturday of the Month Market Series

 Sat Nov 02 2024 at 09:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650

It's All Good Summer Concert Finale

 Sat Oct 19 2024 at 07:00 pm Leonardtown Square

Veterans Day Parade and Memorial Wreath Laying Ceremony

 Mon Nov 11 2024 at 11:00 am Town of Leonardtown

RSP Rattlesnake Pete at Port of Leonardtown Winery

 Sat Oct 26 2024 at 02:00 pm Port of Leonardtown Winery

Small Business Saturday with The Grinch & Cindy Lou Who

 Sat Nov 30 2024 at 10:00 am Town Market LLC

Trunk or Treat

 Sat Oct 19 2024 at 01:00 pm 22850 Washington St PO Box 1756, Leonardtown, MD

Bootleggers at Oysterfest

 Sun Oct 20 2024 at 02:00 pm St. Mary's County Fairgrounds

Southern MD Christian Woman's Brunch & Fellowship - October 26, 2024

 Sat Oct 26 2024 at 09:30 am Ye Olde Towne Cafe Free

SANTA + COOKIE Decorating

Sat Dec 07 2024 at 10:00 am Starrella Photography by Aprilynn

3rd Year Anniversary Pawty

 Sat Dec 07 2024 at 12:00 pm EarthWise Pet Leonardtown

Come Out and See the Grinch & Christmas Shopping Spree

 Sat Dec 14 2024 at 10:00 am Town Market LLC

US Bands - Competition @ Leonardtown High School

 Sat Oct 12 2024 at 08:00 am Leonardtown High School

2024 Leonardtown Veterans Day Parade

Mon Nov 11 2024 at 09:00 am St. Mary's Ryken High School

Bob Pinnola is back in Maryland playing at the Port of Leonardtown Winery on Nov. 23rd, 2pm-5pm

 Sat Nov 23 2024 at 03:00 pm Port of Leonardtown Winery

Taylor Swift Party

 Tue Oct 15 2024 at 06:00 pm Antoinette’s Garden USD 15

PADI Open Water Scuba Diver Course

 Sat Nov 09 2024 at 09:00 am Csm Leonardtown Campus

Holiday Market with The Grinch & Cindy Lou Who

 Fri Nov 29 2024 at 10:00 am Town Market LLC

"Harvest Pumpkin" Spa

 Fri Nov 01 2024 at 10:00 am EarthWise Pet Leonardtown

Trunk or Treat

 Sat Oct 26 2024 at 12:00 pm Town Market LLC

Movie Night featuring The Polar Express

 Fri Dec 06 2024 at 07:30 pm Town Market LLC

Pictures with Santa Clause

Sat Dec 21 2024 at 10:00 am Town Market LLC

Get Unstuck & Unleash Your Potential for Women Workshop -Leonardtown Wharf

 Sat Jun 29 2024 at 10:00 am 22350 N Washington St USD 125

Fall Wellness Day

 Sun Oct 20 2024 at 10:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650

PADI Open Water Scuba Diver Course

 Sat Oct 05 2024 at 08:00 am Csm Leonardtown Campus
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