You’ll Love These 3 Annapolis Waterfront Restaurants!

In the mood for award-winning seafood or fresh country favorites? What about light, farm-to-table fare? No matter what you’re craving, you’ll discover an array of delicious dishes here on the Eastern Shore of Maryland. Historic Chestertown offers an abundance of great food, but Annapolis day-trippers will be happy to know that there are plenty of beloved, coastal eateries to choose from. Below, we’ve compiled just a few of our favorite Annapolis waterfront restaurants. For a complete list of the area’s best cafes, fine dining spots, and seafood spots, be sure to request access to our free Eastern Shore Travel Guide!

3 of the Best Annapolis Waterfront Restaurants

Carroll’s Creek Cafe

When it comes to coastal Maryland fare with a local touch, Carroll’s Creek Cafe is one of the best spots in Annapolis. There’s nothing finer than enjoying a delicious meal as you take in gorgeous Annapolis Harbor views and cool breezes from your seat on the patio! We recommend ordering a specialty seafood dish like the Maryland crab soup or scallops. Carroll’s also serves a fabulous Sunday brunch! Be sure to view the menu and make a reservation (reservation-holders are given preferential seating).

Chart House

Looking for the perfect date night spot in Annapolis? Chart House offers steakhouse classics, salads, a variety of seafood, and panoramic views of the Annapolis Harbor. Though this restaurant is not necessarily local, diners rave about its sunset views, large menu, and coastal ambiance. Reservations are recommended, but not required.

Blackwall Hitch

Blackwall Hitch is an upscale-casual restaurant that serves tasty New American fare. The best part? Outdoor seating (on the rooftop) provides up-close-and-personal views of the surrounding waterway. Whether you’re in the mood for seafood, flatbreads, or just a cocktail or two, Blackwall Hitch is a great choice.

Come Back to Comfort (and Tasty Food) in Historic Chestertown

Wine, Dine, and Relax at Brampton InnBrampton breakfast

Here at Brampton Inn, good food is our bread and butter. That’s why we serve each of our guests a complimentary breakfast featuring fresh juice, handmade pastries, and homemade specialties like our beloved blueberry pancakes and Eggs Benedict—always crafted with love. We also offer Tea Time and Social Hour each afternoon. While we may not be on the water, we offer a perfect opportunity for you to sit back, relax, and enjoy some delicious sweets and savories hand-crafted by our talented in-house pastry chef!

Elegant Accommodations

After a fun-filled day exploring Annapolis and historic Chestertown, get a good night’s rest at Brampton Inn! Our comfortable and welcoming B&B is in the heart of the countryside but less than two miles away from the restaurants and attractions of downtown Chestertown. Our inn features unique amenities like wood-burning fireplaces, a grand front porch, and 20 acres of pastoral beauty. Each of our bright and airy suites and cottages is appointed with guest comfort in mind. There’s no better way to relax—book your stay today!

Ready for a taste of Maryland’s Eastern Shore? Check our availability today! We can’t wait to welcome you.