A charming historic district filled with local art galleries, unique shops, historic landmarks, and local cafes to explore.
If the weather allows, this is a local favorite for a peaceful walk or fresh air. Take the scenic trail through the woods and meadows down to a secluded bayfront beach with incredible views.
Perfect for a day trip across the Bay Bridge. Take a walk along the harbor at Ego Alley, grab lunch on Main Street, explore local shops, or tour the beautiful Naval Academy grounds. Please remember that the Chesapeake Bay Bridge can have traffic and can be difficult to cross if there is inclement weather. We recommend leaving Annapolis no later than 3:00 PM.
A scenic Kent Island winery featuring estate-grown wines, live music, fresh local oysters, and gorgeous Chester River waterfront views.
A relaxing, dog-friendly waterfront winery on Kent Island featuring local wine tastings and scenic bay views accessible by car or boat.
A fun Kent Island craft brewery serving up house-brewed beers, artisan pizzas, live entertainment, and good times.
A classic waterfront landmark serving signature Eastern Shore crab cakes, local seafood, and traditional fare with panoramic views of the Narrows.
The perfect spot to kick back right on the water and experience a true Eastern Shore tradition with fresh steamed crabs, orange crushes, and waterfront views.