John Wilkes Booth: Chasing Lincoln's Assassin Byway Events Plan your road trip on our Byways to visit during local special events and enjoy an authentic Maryland experience. Filter Results: September (395) October (589) November (286) December (271) January (71) February (49) March (30) April (27) May (20) June (12) July (9) August (8) Cities Coltons Point (1) Dowell (2) Drayden (3) Leonardtown (12) Mechanicsville (2) Port Republic (3) Prince Frederick (3) St. Mary's City (3) Regions Southern Maryland (29) Types Fairs & Festivals (4) Food & Drink (1) History & Heritage (10) Literary Arts (1) Miscellaneous (8) Multicultural (6) Nature & Outdoor (5) Performing Arts (4) Sports (1) Visual Arts (17) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters September 17-28, 2025 North End Gallery's 39th Anniversary Show Leonardtown Learn More September 18-28, 2025 North End Gallery's 39th Anniversary Show Leonardtown Learn More September 19, 2025 HOT ROD Drag Week 2025 Presented by Gear Vendors Mechanicsville Learn More September 19-28, 2025 North End Gallery's 39th Anniversary Show Leonardtown Learn More September 20-October 18, 2025 Drayden African American Schoolhouse Open House Drayden Learn More September 20-28, 2025 North End Gallery's 39th Anniversary Show Leonardtown Learn More September 20-21, 2025 Artsfest '25 at Annmarie Dowell Learn More September 21, 2025 Dinner & a Cruise Series at St. Clement's Island Museum Coltons Point Learn More September 21-28, 2025 North End Gallery's 39th Anniversary Show Leonardtown Learn More September 21, 2025 Artsfest '25 at Annmarie Dowell Learn More September 22-28, 2025 North End Gallery's 39th Anniversary Show Leonardtown Learn More September 23-28, 2025 North End Gallery's 39th Anniversary Show Leonardtown Learn More Pagination First previous Current page 1 Page 2 Page 3 Next Last