Guests of the Manor will enjoy these Chestertown area restaurants. Each is in the area surrounding the Inn and offers unique menus with a distinctly Maryland cuisine.

Restaurants in Chestertown

8 miles from Great Oak Manor

The Kitchen at the Imperial Hotel
(410) 778-5000 | 208 High Street
Chef-Owned restaurant. Great bar. Sidewalk dining in nicer weather.


Osprey Point Inn Dining Room

20786 Rock Hall Ave, Rock Hall, MD 21661


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


Italian pasta dish

The Landing at Safe Harbor Great Oak Landing Marina
(410) 778-2020 | next door to Great Oak Manor

The Retriever Bar and The Decoy Bottle Shop
(410) 778-1386 | 37 ½ High Street

Casa Carmen

410.390.9921 | 312 Cannon Street, Chestertown

Cafe Sado
(410) 778-6688 | 870 High Street

fresh oysters

Uncle Charlie’s Bistro
(410) 778-3663 | 848-B High St.

Watershed Alley
(443) 282-9797 | 337 High Street

steaks on a grill

Evergrain Bread Company
(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.


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

plate of seafood


At the Manor



fireside dinner