Best events this weekend in Leonardtown

Date and Time

Fri, 26 Dec, 2025 - 08:00 PM

Location

The Rex, 22695 MD-326, Leonardtown, MD 20650-3885, United States

ALL SINNERS NIGHT – DEC 26 @ THE REX FREE SHOW Featuring SMOKE SIGNALS & DJ Papers ‘Tis the season… to misbehave. We’re throwing the wildest post-Christmas party in Southern Maryland and you’re officially invited. NAUGHTY CHRISTMAS: Santa dresses... Read More

Date and Time

Sat, 27 Dec, 2025 - 06:00 PM

Location

22660 Washington St, 22660 Washington Street, Leonardtown, United States

USD 27

Immerse yourself in a relaxing sound bath journey to unwind, destress, and rejuvenate your mind, body, and soul!About this EventSound bath JourneyJoin us for a transformative exper... Read More

Date and Time

Sat, 27 Dec, 2025 - 07:00 PM

Location

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

Sign ups start at 6pm Darts Fly at 7pm 501/Cricket/CC One leg Loser Bracket Location: Action Lounge 25470 Point Lookout Rd Leonardtown, MD 20650... Read More

Date and Time

Sat, 27 Dec, 2025 - 09:00 PM

Location

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

✨ Welcome to the Pit ✨ The Rex is going FULL frat house basement vibes for one night only — neon lights, cheap drinks, chaotic energy, and 2008–2012 bangers all night. Dress to represent your favorite FRAT or COLLEGE. Frat letters, sorority shirts, coll... Read More

Date and Time

Sat, 27 Dec, 2025 - 02:00 PM

Location

Port of Leonardtown Winery, 23190 Newtowne Neck Rd,Leonardtown, Maryland, United States

Bob Pinnola and his daughter Rosa Hance are playing music in southern Maryland at their favorite winery… Port of Leonardtown Winery. Live music. Variety of fine wines and beverages. Tasty food. Family friendly. Come join us!🍷🎶... Read More