Make your life happening by enrolling to entertainment events in Leonardtown. Find a partner through a salsa night or take your partner to live in concerts by upcoming bands in your town. Get high while playing Beer Pong in a pub crawl or attending stand-up comedy events in Leonardtown. Shake your legs in the happy streets, zumba or dance workshops or go for a film screening in the nearby cafes or theaters.
Explore Entertainment Events in Leonardtown.
| Date | Event | Venue |
|---|---|---|
| 24 May 2025 | Public Domain Restoration Dance Party | The Rex, Leonardtown |
| 30 May 2025 | (Friday event Salsa On The Vine at The Port of Leonardtown Winery. | Port of Leonardtown Winery |
| 20 Sep 2025 | Vendors of Southern MD | Town Market LLC, Leonardtown |
| 18 Oct 2025 | Levi Stephens LIVE | 22845 Washington Street. Unit C, Leonardtown, MD |
| 20 Jul 2025 | Bob Pinnola at Port of Leonardtown Winery on July 20th 2pm-5pm. | Port of Leonardtown Winery |
| 15 Jun 2025 | Free Admission for Dads on Fathers Day at the St. Marys County Museums | St. Mary's County, Maryland, Leonardtown |
| 06 Sep 2025 | Hot Ice Live Port Of Leonardtown Winery | Port of Leonardtown Winery |
| 29 Nov 2025 | Small Business Saturday with The Grinch & Cindy Lou Who | Town Market LLC, Leonardtown |
| 07 Jun 2025 | PBR NIGHT The Rex | 22695 Washington St, Leonardtown, MD |
| 25 Oct 2025 | Trunk or Treat & Vendor Show | Town Market LLC, Leonardtown |
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