Whether you prefer country favorites, fantastic seafood, or light, farm-to-table bites, you’ll find exactly what you’re craving on the Eastern Shore of Maryland. Located in the heart of historic Chestertown, Brampton Inn is the perfect place to experience the Eastern Shore’s homegrown culinary scene. Our guests love the region’s bayfront eateries, intimate cafes, and fine dining spots. It’s time you experienced it for yourself! We’ve compiled just a few of our favorite restaurants in Chestertown, MD. For a complete list of the area’s most beloved eateries, request access to our complimentary Eastern Shore Travel Guide!

Wine, Dine, and Relax at Brampton Inn

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. This is 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!

We feed you well here at Brampton Inn, but there are plenty more fantastic restaurants to discover during your getaway to historic Chestertown. Here are just a few of our favorites!

Some of Our Favorite Chestertown, MD, Restaurants

The Kitchen at the Imperial HotelHomemade Spicy Shrimp Tacos with Coleslaw and Salsa

(410) 778-5000

This spot is closed on Tuesdays, but offers exceptional food! We partner with The Kitchen at the Imperial Hotel when we do our wine pairing dinners for guests.

Luisa’s Cucina Italiana

(410) 778-5360

Luisa’s is a little slice of Italy in the heart of historic Chestertown. This restaurant and pizzeria is open every day of the week. We think it’s pretty darn good!

Evergrain Bread Company

(410) 778-3333

Evergrain Bread Company is a fantastic European-style bakery serving light lunches, sweet treats, and delicious espresso. We have two favorite places to catch up on local gossip, and this is one of them!External view of The Fish Whistle in Chestertown, MD

The Fish Whistle

(410) 778-3566

The Fish Whistle is a Chestertown institution! With beautiful waterfront views and very good food, it’s no wonder. This popular spot is open every day of the week.

Play It Again Sam’s

(410) 778-2688

Open most days of the week, Play It Again Sam’s offers coffee-house vibes and light lunch options. This is another one of our favorite spots to chat about town happenings!

Uncle Charlie’s Bistro

(410) 778-3663

Uncle Charlie’s Bistro offers an upscale menu with a little bit of everything! This spot is open every day for lunch and dinner.

Other Fantastic Restaurants Near Chestertown, MD

Barbara’s on the Bay (Betterton)

(410) 348-3079

At Barbara’s on the Bay, you’ll be met with plenty of classic comfort food and spirits. We recommend grabbing a seat on the deck—this spot offers exceptional views of the Sassafras River!

Molly Mason’s (Kennedyville)

(410) 348-2430

Molly Mason’s is a great spot to eat if you’re in the mood for burgers, fries, and the like. This restaurant is open every day of the week.

Osprey Point Restaurant (Rock Hall)crabs in Chestertown, MD

(410) 639-2762

If you’re looking for a fine dining spot, Osprey Point in Rock Hall is a great option! The food is a bit pricey, but perfect for a fancy night out with that special someone. Osprey Point is closed Mondays, Tuesdays, and for the entire month of January.

Waterman’s Crab House at Sharp Street Wharf (Rock Hall)

(410) 639-2261

Waterman’s Crab House is a casual, waterfront restaurant that serves a variety of scrumptious seafood and offers live music on weekends. This is the only restaurant in our area offering steamed crabs in the summer! Keep in mind that this eatery is closed during the winter months.

Want More Local Restaurant Suggestions?

As local foodies, we know a thing or two about the best spots to dine on the Eastern Shore of Maryland! If you’d like more local insight into the best restaurants around Chestertown, MD, be sure to access our free Eastern Shore Travel Guide! It’s the best resource for helping you plan the perfect Maryland getaway (and satisfy everyone’s cravings).

Ready for a taste of Chestertown? Book your stay with us now and start looking forward to a rejuvenating trip to the Eastern Shore of Maryland!