Entertainment events in Leonardtown

• Fri, 28 Nov, 2025 - 08:00 PM

  Ugly Sweater Party at The Rex featuring In Too Deep

  The Rex Theatre

  31+ Interested
• Fri, 28 Nov, 2025 - 04:30 PM

  Christmas on the Square & Annual Tree Lighting

  Town of Leonardtown

  2887+ Interested
• Sat, 13 Dec, 2025 - 07:00 PM

  Hope In Harmony Winter Concert Series - Noel

  Leonardtown High School

  65+ Interested
• Sat, 20 Dec, 2025 - 08:00 PM

  Social’s Naughty Santa Party!

  41655 Fenwick St, Leonardtown, MD

  150+ Interested
• Wed, 26 Nov, 2025 - 08:00 PM

  2ND ANNUAL DRINKSGIVING DECADES PARTY!

  The Rex Theatre

  184+ Interested
• Thu, 20 Nov, 2025 - 07:00 PM

  Hawthorne Heights in Leonardtown

  The Rex
• Mon, 15 Dec, 2025 - 07:00 PM

  St. Maries Choral Arts Home Concert Carol Sing

  First Saints Community Church

  70+ Interested
• Fri, 21 Nov, 2025 - 06:00 PM

  Paws & Popcorn Night featuring Homeward Bound: The Incredible Journey

  41665 Fenwick St. #13, Leonardtown, MD

  26+ Interested