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.
Shopping

Local Provisions in Rock Hall, Maryland: Small Town Charm, Fresh Finds
There’s something special about life in a small town—and in Rock Hall, Maryland, that something often comes in the form of fresh seafood, hand-picked flowers, and scoops of locally loved ice cream. Whether you’re a longtime resident or planning to make Rock Hall your...

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...