Get ready to kick off your end-of-summer weekend in exciting style with the 36th annual Caroline Summerfest, happening Friday and Saturday, August 15–16, 2025, from 5:00 to 9:00 p.m., in the heart of Downtown Denton. This fun, free, family-friendly arts and entertainment festival transforms Market Street into a bustling hub of live music, artisans, and unforgettable community energy. Groove to two stages of local and regional performers, including a Friday evening showdown featuring high school marching bands, and enjoy strolling entertainers, games, and plenty of food provided by local non-profits. Add some sparkle with Saturday’s fireworks over the Choptank River, check out the Friday-night Car Show, or paddle the Rivah Run!
The event brings together artists, volunteers, and local businesses—all supported by the Town of Denton, Caroline County Recreation & Parks, the Maryland State Arts Council, and many sponsors—making it a true celebration of community spirit.
For smooth arrival and parking, enjoy the free shuttle service from the Health and Public Services Building off 6th Street—so you can focus on fun, not logistics.
Whether you’re a longtime fan or discovering Summerfest for the first time, it’s the perfect way to say goodbye to summer and hello to fall with friends, laughter, and hometown pride. Learn more at carolinesummerfest.com.
Photo by Mickey Pullen
