What are the top free Events happening in Leonardtown?

Here are the top free Events in Leonardtown: SOMD Wine in White: Studio 54 Edition | The Ultimate Disco Revival is happening on Sat 25 Jul 2026 from 5:30 PM onwards at Olde Breton Inn, Leonardtown

What are the Events happening in Leonardtown This Weekend January 23-25 2026?

Here are the Events happening this weekend January 23-25 2026 in Leonardtown: Luck of the Draw is happening on Sat 24 Jan 2026 from 7:00 PM onwards at 25470 Point Lookout Rd Leonardtown, MD 20650 Salsa on the Vine- Jan is happening on Sat 24 Jan 2026 from 6:15 PM onwards at 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 Re-Activate – Scuba Refresher Program Weekend Course is happening on Sun 25 Jan 2026 from 12:00 PM onwards at College of Southern MD-Leonardtown Discover Scuba Diving – Try Scuba Experience is happening on Sat 24 Jan 2026 from 8:00 AM onwards at College of Southern MD-Leonardtown Escape to the Tropics Party 🌴🐠 is happening on Sat 24 Jan 2026 from 6:00 PM onwards at 21935 Society Hill Rd, Leonardtown, MD

What Events are happening in Leonardtown Today January 20 2026?

Here are the Events happening today January 20 2026 in Leonardtown: AP & Dual Enrollment Information Night is happening on Tue 20 Jan 2026 from 6:00 PM onwards at Dr. James A. Forrest Career and Technology Center, Leonardtown

What are the top Events happening in Leonardtown?

Here are the top Events in Leonardtown: 🚨 WAKA FLOCKA FLAME LIVE at The Rex Theater! 🚨 is happening on Thu 22 Jan 2026 from 7:00 PM onwards at 22695 Washington St, Leonardtown, MD, United States, Maryland 20650 Luck of the Draw is happening on Sat 24 Jan 2026 from 7:00 PM onwards at 25470 Point Lookout Rd Leonardtown, MD 20650 Foreign Company-The Rex Theater Leonardtown MD is happening on Sat 31 Jan 2026 from 8:00 PM onwards at The Rex, Leonardtown Spring Fling Open Market & Car Show is happening on Sun 26 Apr 2026 from 8:00 AM onwards at 22675 Washington Street, The Bell Bldg, Leonardtown MD SDVFDRS Auxiliary Spring Craft Vendor Fair & Community Yard Sale is happening on Sat 07 Mar 2026 from 7:00 AM onwards at St. Mary's County Fairgrounds, Leonardtown Anti-Valentines Day Event is happening on Fri 13 Feb 2026 from 8:00 PM onwards at 41655 Fenwick St, Leonardtown, MD 2026 SOUPER Bowl! is happening on Sat 07 Feb 2026 from 5:30 PM onwards at 22730 Washington St, Leonardtown, MD, United States, Maryland 20650 Salsa on the Vine- Jan is happening on Sat 24 Jan 2026 from 6:15 PM onwards at 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 Hot Ice Live @ Action Lounge and Billiards is happening on Sat 28 Feb 2026 from 8:00 PM onwards at 25470 Point Lookout Rd, Leonardtown, MD 20650-3828, United States Galentine's Sip & Shop Happy Hour is happening on Thu 12 Feb 2026 from 6:00 PM onwards at 22695 Washington St, Leonardtown, MD, United States, Maryland 20650

What are the Events happening in Leonardtown this January 2026?

Here are the Events happening in Leonardtown in January 2026 : 🚨 WAKA FLOCKA FLAME LIVE at The Rex Theater! 🚨 is happening on Thu 22 Jan 2026 from 7:00 PM onwards at 22695 Washington St, Leonardtown, MD, United States, Maryland 20650 Luck of the Draw is happening on Sat 24 Jan 2026 from 7:00 PM onwards at 25470 Point Lookout Rd Leonardtown, MD 20650 Foreign Company-The Rex Theater Leonardtown MD is happening on Sat 31 Jan 2026 from 8:00 PM onwards at The Rex, Leonardtown Salsa on the Vine- Jan is happening on Sat 24 Jan 2026 from 6:15 PM onwards at 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 Re-Activate – Scuba Refresher Program Weekend Course is happening on Sun 25 Jan 2026 from 12:00 PM onwards at College of Southern MD-Leonardtown

All Events in Leonardtown, Today and Upcoming Events in Leonardtown

Events in Leonardtown

Thu, 22 Jan, 2026 - 07:00 PM

🚨 WAKA FLOCKA FLAME LIVE at The Rex Theater! 🚨

22695 Washington St, Leonardtown, MD, United States, Maryland 20650

33+ Interested
Sat, 24 Jan, 2026 - 07:00 PM

Luck of the Draw

25470 Point Lookout Rd Leonardtown, MD 20650

7+ Interested
Sat, 31 Jan, 2026 - 08:00 PM

Foreign Company-The Rex Theater Leonardtown MD

The Rex

164+ Interested
Sun, 26 Apr, 2026 - 08:00 AM

Spring Fling Open Market & Car Show

22675 Washington Street, The Bell Bldg, Leonardtown MD

229+ Interested
Sat, 07 Mar, 2026 - 07:00 AM

SDVFDRS Auxiliary Spring Craft Vendor Fair & Community Yard Sale

St. Mary's County Fairgrounds

136+ Interested
Fri, 13 Feb, 2026 - 08:00 PM

Anti-Valentines Day Event

41655 Fenwick St, Leonardtown, MD

16+ Interested
Sat, 07 Feb, 2026 - 05:30 PM

2026 SOUPER Bowl!

22730 Washington St, Leonardtown, MD, United States, Maryland 20650
Sat, 24 Jan, 2026 - 06:15 PM

Salsa on the Vine- Jan

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

53+ Interested
Sat, 28 Feb, 2026 - 08:00 PM

Hot Ice Live @ Action Lounge and Billiards

25470 Point Lookout Rd, Leonardtown, MD 20650-3828, United States

17+ Interested
Thu, 12 Feb, 2026 - 06:00 PM

Galentine's Sip & Shop Happy Hour

22695 Washington St, Leonardtown, MD, United States, Maryland 20650

482+ Interested
Fri, 13 Feb, 2026 - 06:15 PM

Galentines COOKIE decorating class

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

35+ Interested
Sat, 14 Mar, 2026 - 08:00 PM

Social's St Patrick's Day Event

41655 Fenwick St, Leonardtown, MD, United States, Maryland 20650

28+ Interested
Sun, 25 Jan, 2026 - 12:00 PM

Re-Activate – Scuba Refresher Program Weekend Course

College of Southern MD-Leonardtown
Thu, 19 Feb, 2026 - 06:30 PM

Tapas & Wine Pairing at SOCIAL

Social on Fenwick

USD 77
Fri, 30 Jan, 2026 - 06:15 PM

Charcuterie Date Night w/ Hicks Creations

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

55+ Interested
Sat, 04 Apr, 2026 - 09:00 AM

First Saturday of the Month Market Series

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

7+ Interested
Sat, 07 Feb, 2026 - 11:00 AM

Valentines Day Event at MJ Luxe Medi Spa

25450 Point Lookout Rd Suite 1, Leonardtown, MD

195+ Interested
Sun, 22 Feb, 2026 - 01:00 PM

February - Sip and Knit Workshop

23600 N Montague Dr, Leonardtown, MD 20650-5865, United States
Fri, 13 Feb, 2026 - 08:30 PM

Silent book club-SOMD Feb 2026

Antoinette's Garden

33+ Interested
Thu, 22 Jan, 2026 - 05:30 PM

Forrest Center Tech Expo

Dr. James A. Forrest Career and Technology Center

79+ Interested
Sat, 31 Jan, 2026 - 08:30 AM

Men's Breakfast

22730 Washington St, Leonardtown, MD, United States, Maryland 20650
Sat, 11 Apr, 2026 - 08:30 AM

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

St. Mary's County Recreation & Parks
Sat, 24 Jan, 2026 - 08:00 AM

Discover Scuba Diving – Try Scuba Experience

College of Southern MD-Leonardtown
Thu, 29 Jan, 2026 - 06:00 PM

Historic Lecture: The Brick Chapel at St. Mary's City

41770 Baldridge Street, Leonardtown, MD, United States, Maryland 20650

5+ Interested
Wed, 04 Mar, 2026 - 05:30 PM

Nicotine Cessation Class - Standalone Sessions

21580 Peabody St, Leonardtown, MD, United States, Maryland 20650
Fri, 03 Jul, 2026 - 08:00 PM

St. Mary’s Freedom Fest

St. Mary’s Freedom Fest
Sat, 24 Jan, 2026 - 06:00 PM

Escape to the Tropics Party 🌴🐠

21935 Society Hill Rd, Leonardtown, MD

100+ Interested
Fri, 06 Feb, 2026 - 12:00 AM

Last Day to Submit - Youth Art Month Call for Art!

22660 Washington St., Leonardtown, MD, United States, Maryland 20650
Fri, 30 Jan, 2026 - 09:00 PM

Red Light, Green Light DJ Night

22695 Washington St, Leonardtown, MD, United States, Maryland 20650

35+ Interested
Sat, 24 Jan, 2026 - 08:00 PM

DMATF@The Rex Leonardtown

The Rex

225+ Interested
Sat, 28 Mar, 2026 - 06:15 PM

Ceramic Charcuterie board DYI workshop

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

27+ Interested
Sat, 07 Feb, 2026 - 09:00 PM

Single & Ready to Buck PBR Night @ The Rex

22695 Washington St, Leonardtown, MD, United States, Maryland 20650

31+ Interested
Sun, 25 Jan, 2026 - 12:00 PM

Explore the "Wings of Wellness" at Hope and Healing

23140 Moakley St. Suite 6, Leonardtown, MD, United States, Maryland 20650

7+ Interested
Wed, 04 Feb, 2026 - 06:30 PM

Ladies Night Out Zumba After Dark

26011 point lookout rd leonardtown Md

4+ Interested
Fri, 15 May, 2026 - 06:00 PM

Breton Bay Community Event

Breton Bay Dr, Leonardtown, MD 20650, United States

47+ Interested
Sat, 12 Sep, 2026 - 11:00 AM

Vendors of Southern MD

Town Market LLC

19+ Interested
Sat, 25 Jul, 2026 - 05:30 PM

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

Olde Breton Inn

Free
Tue, 27 Jan, 2026 - 12:00 PM

Women’s Luncheon by JAG Consulting

The Inn at Leonardtown

7+ Interested
Tue, 20 Jan, 2026 - 06:00 PM

AP & Dual Enrollment Information Night

Dr. James A. Forrest Career and Technology Center

34+ Interested
Fri, 06 Feb, 2026 - 10:00 AM

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

41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650
Sat, 14 Feb, 2026 - 09:30 AM

Valentines' Day Sweets & Treats

Town Market LLC

84+ Interested
Thu, 22 Jan, 2026 - 03:30 PM

R&P Instructor Expo

Wellness & Aquatics Center

8+ Interested
Sat, 21 Feb, 2026 - 10:00 AM

Moll Dyer Legend Day Featuring "Chessie" The Chesapeake Sea Monster

Town Market LLC

13+ Interested
Sat, 11 Apr, 2026 - 05:00 PM

Battle by the Bay - Leonardtown, MD

42455 Fairgrounds Rd, Leonardtown, MD 20650, United States

15+ Interested
Sat, 24 Jan, 2026 - 03:00 PM

January Winter Pack Stroll

Shepherd's Old Field Market

42+ Interested

All Upcoming events

in Leonardtown

Charles County Job Fair - Jobseeker Registration

Events in Leonardtown

Events in Leonardtown

🚨 WAKA FLOCKA FLAME LIVE at The Rex Theater! 🚨

Luck of the Draw

Foreign Company-The Rex Theater Leonardtown MD

Spring Fling Open Market & Car Show

SDVFDRS Auxiliary Spring Craft Vendor Fair & Community Yard Sale

Anti-Valentines Day Event

2026 SOUPER Bowl!

Salsa on the Vine- Jan

Hot Ice Live @ Action Lounge and Billiards

Galentine's Sip & Shop Happy Hour

Galentines COOKIE decorating class

Social's St Patrick's Day Event

Re-Activate – Scuba Refresher Program Weekend Course

Tapas & Wine Pairing at SOCIAL

Charcuterie Date Night w/ Hicks Creations

First Saturday of the Month Market Series

Valentines Day Event at MJ Luxe Medi Spa

February - Sip and Knit Workshop

Silent book club-SOMD Feb 2026

Forrest Center Tech Expo

Men's Breakfast

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

Discover Scuba Diving – Try Scuba Experience

Historic Lecture: The Brick Chapel at St. Mary's City

Nicotine Cessation Class - Standalone Sessions

St. Mary’s Freedom Fest

Escape to the Tropics Party 🌴🐠

Last Day to Submit - Youth Art Month Call for Art!

Red Light, Green Light DJ Night

DMATF@The Rex Leonardtown

Ceramic Charcuterie board DYI workshop

Single & Ready to Buck PBR Night @ The Rex

Explore the "Wings of Wellness" at Hope and Healing

Ladies Night Out Zumba After Dark

Breton Bay Community Event

Vendors of Southern MD

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

Women’s Luncheon by JAG Consulting

AP & Dual Enrollment Information Night

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

Valentines' Day Sweets & Treats

R&P Instructor Expo

Moll Dyer Legend Day Featuring "Chessie" The Chesapeake Sea Monster

Battle by the Bay - Leonardtown, MD

January Winter Pack Stroll

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