Chestertown Restaurants

Java Rock

The Front Room

208 High St

Osprey Point Restaurant

20786 Rock Hall Ave
At the Inn at Osprey Point

Reiley's on the River

98 Cannon St
On the water

Blue Heron Cafe

236 Cannon St

Bay Wolf

Waterman's Crab House Restaurant & Dock Bar

Bay Leaf Gourmet

5757 Main St

Catch the real flavor of Chestertown. From street stalls to elegant dining rooms, paper plates to fine china, restaurants will be one of your best glimpses into the heart, soul and belly of life in Chestertown - and definitely your most delicious. Loosen your belt and dig in.