All Upcoming events

• 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

  158+ Interested
• Sat, 24 Jan, 2026 - 06:15 PM

  Salsa on the Vine- Jan

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

  40+ Interested
• Fri, 16 Jan, 2026 - 08:00 PM

  Justin Allen

  22785 Washington St, Leonardtown, MD
• Thu, 22 Jan, 2026 - 05:30 PM

  Forrest Center Tech Expo

  Dr. James A. Forrest Career and Technology Center

  79+ 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
• Sun, 26 Apr, 2026 - 08:00 AM

  Spring Fling Open Market & Car Show

  22675 Washington Street, The Bell Bldg, Leonardtown MD

  110+ Interested
• Sat, 07 Mar, 2026 - 07:00 AM

  SDVFDRS Auxiliary Spring Craft Vendor Fair & Community Yard Sale

  St. Mary's County Fairgrounds

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

  January Winter Pack Stroll

  Shepherd's Old Field Market

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

  Galentine's Sip & Shop Happy Hour

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

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

  Galentines COOKIE decorating class

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

  35+ Interested
• Fri, 16 Jan, 2026 - 06:15 PM

  Sip & Paint night Jan 2026

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

  54+ Interested
• 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
• Thu, 15 Jan, 2026 - 06:00 PM

  Real Modern Yoga

  41566 Medleys Neck Road, Leonardtown, MD

  4+ Interested
• Fri, 16 Jan, 2026 - 06:15 PM

  Paint and Sip

  Port of Leonardtown Winery

  28+ 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
• Sun, 25 Jan, 2026 - 12:00 PM

  Re-Activate – Scuba Refresher Program Weekend Course

  College of Southern MD-Leonardtown
• Fri, 30 Jan, 2026 - 06:15 PM

  Charcuterie Date Night w/ Hicks Creations

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

  41+ Interested
• Thu, 15 Jan, 2026 - 06:00 PM

  Team Trivia

  21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650

  5+ 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
• 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
• Thu, 15 Jan, 2026 - 07:00 PM

  Wes Ryce

  22785 Washington St, Leonardtown, MD

  12+ Interested
• Sat, 24 Jan, 2026 - 06:00 PM

  Escape to the Tropics Party 🌴🐠

  21935 Society Hill Rd, Leonardtown, MD

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

  AP & Dual Enrollment Information Night

  Dr. James A. Forrest Career and Technology Center

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

  Ladies Night Out Zumba After Dark

  26011 point lookout rd leonardtown Md

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

  Valentines Day Event at MJ Luxe Medi Spa

  25450 Point Lookout Rd Suite 1, Leonardtown, MD

  132+ 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
• Thu, 22 Jan, 2026 - 03:30 PM

  R&P Instructor Expo

  Wellness & Aquatics Center

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

  February - Sip and Knit Workshop

  23600 N Montague Dr, Leonardtown, MD 20650-5865, United States
• Sun, 18 Jan, 2026 - 01:00 PM

  Beginner Plus Two Chunky Yarn Hand Kit Workshop

  Refined Beauty: Permanent Makeup & Lash Artistry

  19+ Interested
• Fri, 13 Feb, 2026 - 08:30 PM

  Silent book club-SOMD Feb 2026

  Antoinette's Garden

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

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

  Town Market LLC

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

  Men's Breakfast

  22730 Washington St, Leonardtown, MD, United States, Maryland 20650
• Sat, 11 Apr, 2026 - 05:00 PM

  Battle by the Bay - Leonardtown, MD

  42455 Fairgrounds Rd, Leonardtown, MD 20650, United States

  15+ 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

  23+ Interested
• Sun, 18 Jan, 2026 - 01:00 PM

  January - Sip and Knit Workshop

  23600 N Montague Dr, Leonardtown, MD 20650-5865, United States

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

  Nicotine Cessation Class - Standalone Sessions

  21580 Peabody 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

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

  DMATF@The Rex Leonardtown

  The Rex

  225+ 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

  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