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 & bar.

Italian pasta dish

The Landing at Safe Harbor Great Oak Landing Marina
(410) 778-2020 | next door
Operates April 15-October 15. Closed on Tuesdays.

The Retriever Bar and The Decoy Bottle Shop
(410) 778-1386 | 37 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 Street
Fusion of French and Southeast Asian cuisine and features diverse sushi
Open Daily Noon-2:30 & 5-9

fresh oysters

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

Watershed Alley
(443) 282-9797 | 337 High Street
Simple, authentic, and delicious local dishes
Open for dinner Wednesday-Saturday, 5-9

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

steaks on a grill

(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 Avenue
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

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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