Things To Do
Modern Stone Age Kitchen
236 Cannon Street, Chestertown, MD 21620
A Rubin favorite! Sourdough kitchen serving breakfast, brunch, sandwiches/salads, pizza on Friday evenings.
Evergrain Bakery
201 High Street, Chestertown, MD
Coffee, pastries, limited selection of breakfast and lunch sandwiches.
Play It Again Sam
14 Washington Square, Chestertown, MD 21620
Yummy sandwiches, easy to grab and go!
The Retriever Bar & Oysters
337 1/2 High Street, Chestertown, MD
Serving delicious cocktails and light meals.
Watershed
377 High Street, Chestertown, MD
Chesapeake Bay centric gourmet dining for lunch and dinner. Reservations necessary. $$$
Bad Alfred's Distilling
323 High Street, Chestertown, MD 21620
Brewpub serving wood-fired pizzas.
Admirals Beachside Bar
21140 Green Lane, Rock Hall, MD 21661
Bar/restaurant at Haven Harbour Marina/Hotel
Blue Heron Oyster House and Inn
20658 Wilkins Avenue, Rock Hall, MD 21661
Oysters, seafood, salads
Waterman's Crab House
21055 West Sharp Street, Rock Hall, MD 21661
Indoor and outdoor bar and dining overlooking Rock Hall Harbor
Chestertown Farmer’s Market
200-300 block of High Street, Chestertown,
Saturdays, 8am - 12pm
Kayak Rental
Great Oak Landing Golf Course
22170 Great Oak Landing Road, Chestertown,
Scenic 9 hole, par 60 course with views of the marina.
Fall Fest
Annual live music, oyster, handicraft event.
Boating
Bareboat sailboat charters
Captained sailing trips
For all the days along the way