Fall into Adventure in Kent County

There’s no better place to experience the magic of autumn than Kent County, Maryland.

This season, our charming waterfront communities invite you to celebrate our maritime heritage through a series of exciting events.

The season kicks off in Rock Hall with Lambert Wickes Day Saturday, Sept. 19. This event honors the Continental Navy captain and local hero in a blend of history and community spirit along the harbor.

Following closely is the 29th annual Rock Hall FallFest on October 10. This beloved festival celebrates Eastern Shore heritage with local oysters, plentiful regional food and a variety of skilled craft vendors.

Throughout the day, the town comes alive with live music, providing a festive backdrop for visitors to explore this quintessential waterman’s town.

In Chestertown, the season culminates with the Sultana Downrigging Weekend from October 30 to November 1.

As one of North America’s largest annual gatherings of tall ships, it offers a breathtaking sight on the Chester River. Visitors can enjoy a high-energy bluegrass festival, ship tours and sails, all while supporting environmental literacy programs.

Beyond the festivals, fall is the ideal time to explore the natural beauty of the Eastern Neck Island National Wildlife Refuge, where migratory birds and scenic trails await.

After your outdoor adventure, wander through the historic, walkable streets of Chestertown and Rock Hall to discover unique boutiques and waterfront dining.

Start planning your visit today, and learn more at kentcounty.com/visitors.

Kent County Tourism is part of The Guide’s Community Connect sponsored content program.