Bring the family to historic Downtown Denton for the Friday Night Cruise-In Car Show, a free, family-friendly evening featuring cars, motorcycles, food, and a DJ spinning oldies on the 200...

Raise a glass for a good cause at Pints for Paws 2026, benefiting the Caroline County Humane Society. Spend the afternoon at The Cow Barn enjoying local breweries, a winery,...

Learn the basics of watercolor painting during this beginner-friendly workshop at The Foundry in Denton led by Dennis Hall. Participants will explore watercolor paints, paper and brushes, practice techniques with...

Enjoy a Maryland crab feast on the Choptank River with River City Cruise Co. This laid-back two-hour cruise includes crabs, shrimp, fried chicken, corn, cornbread, watermelon, dessert and nonalcoholic drinks,...

Join local artist Joanne Gelles for a mixed media collage workshop at the Caroline County Public Library. Using a variety of materials and guided instruction, participants will create an owl-inspired...

Celebrate summer in Downtown Denton at the 37th Annual Caroline Summerfest, a free, family-friendly festival featuring live music, food vendors, artisan booths, nonprofit booths, free kids’ art activities, and more....

Friday, August 21 & Saturday, August 22, 2026, 5–8:30pm Join the Caroline County Historical Society during Summerfest for the 250th Art Challenge Exhibit at the Museum of Rural Life. In...

Take to the water during Caroline Summerfest’s Rivah Run, a fun 2-mile paddling poker run open to children and adults of all ages. Bring any type of paddle craft and...

Take a closer look at two familiar backyard birds with guide Jim Wilson at Adkins Arboretum. Learn about the habitats, migration patterns and breeding habits of American Robins and Blue...