For guests seeking incredible cuisine near our Eastern Shore B&B, these Chestertown, MD restaurants come with our highest personal recommendation. All these premier dining destinations are in the area surrounding the Inn and offer a delicious variety of food with a distinctly Maryland flair.

Restaurants in Chestertown

8 miles from Great Oak Manor

The Kitchen at the Imperial
(410) 778-5000 208 | High Street
Chef-Owned restaurant. Very good food. Great bar. Sidewalk dining in nice weather with your pet is available. Open 7 days, lunch & dinner.

Luisa’s Cafe
(410) 778-5360 849 | Washington Avenue
Home cooked Italian food and gourmet pizza. Ranked #9 in best of Maryland’s Italian restaurants.
Open daily 10-9:00 (closed Holidays)

98 Cannon Riverfront Grille
(443-282-0055) | 98 Cannon Street
Casual cuisine with a view. Outdoor dining ; large dining room and bar.

Italian pasta dish

The Landing at Safe Harbor Great Oak Landing Marina (next door)
Operates April 15-October 15. Closed on Tuesdays.

The Retriever Bar and The Decoy Bottle Shop
337 ½ High Street
Extensive Bar offerings. The back dining room has a great menu. Offering fresh oysters in season.

Cafe Sado
(410) 778-6688 | 870 High St,
Fusion of French and Southeast Asian cuisine and features diverse sushi
Open Daily Noon-2:30 & 5-9

Uncle Charlie’s Bistro
(410) 778-3663 | 848-B High St. (behind Subway, Weird location but good food)
Homemade ice cream, great for lunch
Open Monday-Wednesday 11-8:00
Open Thursday-Saturday 11-9:00

fresh oysters

Bad Alfred’s Distilling
(443-282-0163) | 323 High Street
Wood Fired Pizzas, Craft Beer and Distilled Spirits
Open Thursday-Monday, 11:30 am open

(410) 778-3333 | 201 High Street
Delicious bread, pastries, and coffee and sandwiches
Open Tuesday-Saturday 6:30-5, Sunday 8-2
Closed Monday

Chester River Wine & Cheese
(443-282-0220) | 117 S. Cross St.
Artisan cheeses, meats and delicious wines. Serves lunch outside in nice weather.

Procolino’s Pizza
(410) 778-5900 711 | Washington Ave, Suite 9
Open daily 10-10

wood fired pizza

Restaurants in the Town of Rock Hall

12 miles from Great Oak Manor

Inn at Osprey Point
(410) 639-2194 | 20786 Rock Hall Avenue
Regional cuisine with talented chef, best in Rock Hall
Open for dinner Wednesday-Sunday 5-8 (February-December)

(410) 639-2261 | 21055 Sharp Street
Best crab house, live music on Sunday. Open Daily

Bay Wolf
(410) 639-2000 | Rt. 20
Austrian/Regional cuisine
Open Monday-Saturday 12-9, closed Sunday

plate of seafood

Harbor Shack
(410) 639-9996 | 20895 Bayside Ave
Bay front restaurant and bar
Open Thursday 11:30-8:30, Friday-Saturday 11:30-9:30, Sunday 11:30-8
Closed Monday-Wednesday


fresh grilled chicken

Restaurants in Betterton

15 miles from Great Oak Manor

Barbara’s on the Bay
So worth the 20 minute drive. Some of the best comfort food you will ever get with her chef’s flair. Uses a lot of local ingredients. The grilled oysters are to die for when in season.
Open Thursday 11:30-8
Open Friday-Saturday 11:30-9 p.m.
Open Sunday Brunch/Lunch 11:30-4

steaks on a grill

At the Manor

crab feast

Crab Feasts

Available late April to early October

1 dozen fresh crabs, steamed; served with corn on the cob steamed (in season); included is a bottle of white wine or a 6 pack of beer. Served waterfront at our Gazebo.

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fireside dinner

Fireside Dinners

Available February & March

Private table by our library fireplace or dining room fireplace. Dinner is a filet, served with a salad, potato or rice dish and another seasonal green vegetable, with a light dessert. Wine not included. May purchase wine or bring your own.

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