Watershed Alley

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337 High St
Chestertown, MD 21620
+1 (443) 282-9797
https://watershedchestertown.com

Imagined within the charming village of Chestertown, Maryland, Watershed Alley emerges as a culinary gem reshaping Eastern Shore dining experiences. Deliberately christened, this eatery masterfully intertwines its menu, ambiance, and architectural aesthetics to showcase the rich tapestry of its local environs.

A nod to the historical roots of the Chesapeake Bay unfurls within the essence of this restaurant. Spanning generations, the Chesapeake Bay watershed has generously bestowed a cornucopia of seafood and farm-fresh produce to the wider Chesapeake region. Watershed Alley elegantly weaves this legacy into its cuisine, setting, and hospitality, presenting innovative dishes that honor traditional elements and local flavors.

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Reviews

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4.560 reviews
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Heidi D.
5/11/2025

This is my 2nd review of The Watershed because it just that good!!!!! This is my favorite place to come when I'm visiting in Chestertown, it never disappoints. Rodney and the entire staff always...

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Jessica D.
9/20/2025

Super accommodating, beautiful atmosphere, and the food was absolutely delicious! Came here while on a retreat with colleagues and this couldn't have been a more perfect place to have dinner on my...

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Erica R.
11/14/2024

Superb dining experience! We LOVED our visit to Watershed. It was simple to make a reservation online. We arrived at the restaurant and were promptly seated in a cozy corner by a window on the...

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Sara W.
11/2/2025

Terrific restaurant in Chestertown. The space is lovely and they make the most of it. We had an amuse bouche of butternut squash arancini - delicious and a great way to start the meal. My husband...

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Ruchi A.
11/18/2024

Came here with a big group and it was great! Everything we ordered was good and the service was excellent. I just wish we had gotten some bread earlier because waiting for meals for 12 took a...

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