Events in January 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