What Are the Best Rock Hall Restaurants?

The Eastern Shore of Maryland is known for so many wonderful things: Rich history, beautiful Chesapeake Bay views, and, of course, iconic coastal cuisine! If you have a hankering for award-winning crab, Chesapeake-caught fish, or sophisticated seasonal selections, you need to pay a visit to Maryland’s Eastern Shore! One of the best spots for fantastic food is the town of Rock Hall, Maryland. Below, we’ve listed just a few of our guests’ favorite Rock Hall restaurants! For more of our best local recommendations, be sure to access our free Travel Guide to the Eastern Shore of Maryland.

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Treat Your Taste Buds at These 4 Rock Hall Restaurants

The Pearl on Main

The Pearl on Main’s motto is: “Life’s too short for ordinary food.” Guests of Brampton Inn agree that this Diners’ Choice Award winner’s food is anything but ordinary! This sophisticated, new addition to Rock Hall showcases fresh, local ingredients with an emphasis on seafood. Be sure to try the sweet potato risotto, a signature flatbread, or one of The Pearl on Main’s weekly fish specials. It’s hard to go wrong ordering anything from Executive Chef Paul Brinkley’s menu! Advance reservations are recommended.

Osprey Point Restaurant

Have you ever dreamed of a place where you could arrive by boat, dock, then step ashore for a  fabulous, fine dining meal? You can do just that at the Osprey Point Restaurant! In addition to delicious, seasonal meals (featuring local seafood and vegetables), diners enjoy an intimate bar, homemade desserts, and stunning waterfront views here. Make a dinner reservation online or by calling ahead.

Waterman’s Crab House

If award-winning crab, a laid-back atmosphere, and live music on the weekends tickle your fancy, make a point to stop for a meal at Waterman’s Crab House in Rock Hall. Over 40 years ago, Waterman’s started as a humble seafood market on the Bay. It has evolved into a full-service restaurant offering all manner of local crab, fresh fish, BBQ, and more. Our guests love catching the sunset at this waterfront Rock Hall restaurant!

Harbor Shack

Harbor Shack can be summed up in simple terms: “Cold beer, good food, and nice people.” The staff at this funky Bayfront spot are genuine, funny, and friendly—they expect the same from their guests! The Harbor Shack menu consists of everything from lump crab cake sandwiches and salads to sizzling fajitas and seafood quesadillas. Don’t miss the live music at this Rock Hall bar and grill!

More Delicious Maryland Food Awaits at Brampton Inn!The Green Room at Brampton Inn bed view

Whether you’re here exploring the Eastern Shore of Maryland’s seafood restaurants, sampling the many fun things to do in the Chesapeake Bay area, or simply getting away from it all for a while, Brampton Inn is the best place to stay on Maryland’s Eastern Shore. We’re just a quick 18-minute drive from Rock Hall! You’ll love getting a good night’s sleep in one of our bright, airy, and spacious accommodations and wake up to a freshly prepared breakfast you’ll never forget. Later, join us for tea time and social hour for light snacks and drinks! Finally, end your day “porch surfing” as the sun sets over the horizon. By the end of your first day staying with us, you’ll see why so many people discover their most relaxed (and well-fed) selves here!

Ready for a true taste of Maryland’s Eastern Shore? Book your stay at Brampton Inn! We can’t wait to welcome you to beautiful Chestertown.