Best events this weekend in Leonardtown

Date and Time

Fri, 16 Jan, 2026 - 06:15 PM

Location

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

❄️ Sip & Paint Night – January 16 at 6:15 PM! ❄️ Join us at Port of Leonardtown Winery for a cozy winter evening of creativity and great wine! We’ll be painting a beautiful wintery scene (like the one above!) with step-by-step instructions—perfect fo... Read More

Date and Time

Fri, 16 Jan, 2026 - 06:15 PM

Location

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

🎨 Paint & Sip at Port of Leonardtown Winery 🍷 January 16 • 6:15 PM Get ready for a fun and creative night out! Join us for a Paint & Sip where you’ll enjoy step-by-step instructions to create your own beautiful masterpiece to take home. Each tic... Read More

Date and Time

Sat, 17 Jan, 2026 - 08:00 PM

Location

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

🔥 THE BASSMENT at The Rex — Jan 17th, 2026! 🔥 We’re excited to bring a full 7Soundscape takeover to The Rex Theatre this January. Big bass, stacked lineup, lasers, and a wild night planned. 🎟️ Tickets are live now: https://tix.saints.wtf/ Grab yours ear... Read More

Date and Time

Fri, 16 Jan, 2026 - 06:00 PM

Location

41665 Fenwick St. #13, Leonardtown, MD, United States

Ever wonder what your pets do the moment you walk out the door? Curl up with our café kitties and find out! Bring your curiosity, grab a cozy seat, and let the cats be your movie-night companions—because at Meow Dyer, we already know what pets do when hu... Read More

Date and Time

Sat, 17 Jan, 2026 - 09:00 AM

Location

Leonardtown Library, 41685 Library Pl, Leonardtown, MD 20650, United States

New Year, New WIP! Let's get to work on our needlework projects in the warmth of each other's company!... Read More