The rich tradition of the Chesapeake Bay watershed, updated, refined, and celebrated.
The opening of a new restaurant in the village of Chestertown, Maryland is a watershed event in Eastern Shore dining. 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 true origins of the restaurant can be traced to the origins of the Chesapeake Bay itself. For centuries, the Chesapeake Bay watershed has provided a boundless variety of seafood and local farm food for the greater Chesapeake region. Watershed Alley’s distinctive cuisine, atmosphere, and service draw upon and extend this tradition, offering creative options that highlight traditional ingredients and flavors. Like the succulent oysters on its menu, Watershed Alley captures and filters the bounty of the Chesapeake watershed region: the Chester River, Chesapeake Bay, Atlantic Ocean, and local farms and fields- clean, simple, authentic regional food “from the watershed to the Watershed.”


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.

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.