605 Second St.
Chesapeake City, MD
This is the Eastern Shore’s Maragaritaville: live bands, ample space, a tiki bar and a view of the docks. Come warm weather, there’s no place better between the beaches and Baltimore for a relaxing drink and a bite or a blowout party night.
The Chesapeake Inn offers a different kind of outdoor experience: toddlers, 20-somethings and 60-somethings comingle, each group unfazed by the others. The waterfront deck has a well-stocked tiki bar and views of the Back Creek Basin, C&D Canal and parts of Chesapeake City. Live bands play the lower deck seven days a week from May thru October. The dock menu is casual. Appetizers such as the big crab pretzel and the smoked crab-cheese bruschetta are superb. JoJo’s Gelato and Ice Cream Bar, on the upper deck, scoops several flavors of water ice, which always delights young captains.
Owners of the Chesapeake Inn bill the restaurant as the next best thing to dining at the beach. In many ways, it’s better. The inn is closer, easy to get to and the only traffic jam you’ll find here is during crazy Canal Day. From May through October, the Chesapeake Inn’s deck is the perfect spot to marvel at the trademark Chesapeake City bridge, to watch hulking cargo ships pass on the C&D and to see who’s docking at the marina for a night of fun. Regulars go for the brick oven pizzas, but sandwiches and fried goodies are also served on the deck. Need to get your Jimmy Buffett on? The tiki bar adds to the island atmosphere by cranking out popular rum runners and mojitos while live bands keep it rocking.