There’s something about life on the Chester River that instantly puts you at ease. The water glistens in the afternoon sun, sailboats drift by at a slow pace, and the air feels just a little lighter. Tucked along these scenic banks sits Chester River Landing, one of...
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.
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...
Discover the timeless charm of Downtown Historic Chestertown, a picturesque waterfront town on Maryland’s Eastern Shore. From colonial architecture and rich heritage to vibrant arts, local shops, and scenic riverfront strolls, Chestertown offers history, culture, and small‑town appeal for visitors and residents alike.
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...
Raise a glass and explore the best happy hour spots in Chestertown, Maryland. From waterfront views to craft cocktails and local favorites, these top three picks serve up great vibes and even better drink specials.