Chestertown, Maryland blends Colonial charm, artistic flair, and riverfront beauty. Whether you’re visiting or planning to move, explore the top things to do—from historic strolls to cultural festivals and outdoor fun.
Chestertown
Kentmore Park: A Hidden Waterfront Retreat in Kennedyville, Maryland
Tucked away along the banks of the Sassafras River, Kentmore Park is one of Kent County’s best-kept secrets. Located in Kennedyville, Maryland, this charming waterfront community offers residents a serene and private escape while maintaining easy access to nearby...
The Timeless Charm of Downtown Historic Chestertown
Steeped in colonial history and brimming with small-town charm, Downtown Historic Chestertown is a hidden gem on Maryland’s Eastern Shore. This picturesque waterfront town, located along the Chester River, offers a unique blend of rich heritage, vibrant arts, and a...
Our Favorite Weekend Shopping Destinations in Chestertown
If you're looking for the best places to shop in Chestertown, MD, you're in for a treat! This historic waterfront town is full of charming boutiques, artisan markets, antique stores, and locally owned gems that make shopping here a truly unique experience. Whether...
Top Three Places for Happy Hour in Chestertown, Maryland
Chestertown, Maryland, is a charming historic town that knows how to relax and unwind. Whether you’re looking for a cozy spot to enjoy craft cocktails or a lively atmosphere for a casual drink, the town’s happy hour scene has something for everyone. Here are the top...