Watershed Alley

The aptly named Watershed Alley has designed its food, its setting, and its tasteful architecture to highlight the remarkable resources of its local surroundings.

The menus reflect the long-held commitment of Watershed Alley’s Chef to a combination of fresh ingredients, tasteful simplicity, and beautiful presentations - all inspired by the resources of the Chesapeake Bay watershed.WatershedAlley_1121_211016_100551

The setting includes a strikingly attractive main dining area, an open kitchen, and a unique Chef’s Counter. There is also a ten-person Chef’s Table, that provides a close look at the kitchen and a chance for conversations with the Chef. On the second floor overlooking High Street, the sun-filled porch offers the dining menu in a relaxing space, private dining spaces that seat 14-80 guests, and a bar-lounge area. The bar features pub fare combined with a drink list focused on classic options that pair with the food.



(443) 282-9797
Rodney Scruggs
337 High Street
Chestertown, MD 21620
Days Open
Sun, Wed, Thurs, Fri, Sat
Dinner Wed - Sat 5 - 9 pm//Lunch & Brunch Fri & Sat 11:30 - 2/Sun 11 - 2//Happy Hour Thurs - Sat 3 - 5:30
DCA Member