Watershed Alley

“Absolutely wonderful experience. Very creative menu great service. The happy hour was a great deal but we stayed for the full dinner also. So worth it. Oustanding drinks. also. Chef brought out the best fried oyater we have ever had. definitely make a reservation. It gets busy on weekends.”

“This was our second visit to Watershed Alley. I think we will keep returning every time we visit the area. The waitstaff is friendly and attentive. The food is delicious and artfully presented. My favorite was the Marjolaine dessert with cappuccino. Delightful! The room was packed to capacity by 6:30pm. It was a bit loud - not private. But, I will return for the food. The decor is beautiful. Highly recommend!”

“Enjoyed our meal last night tremendously! Lovely selection of wines from all over the world and beers (my husband was very pleased). We started our meal with the late-autumn salad (me) and the risotto style Farro (husband) ... Both excellent! For entrees we got the bison short ribs (husband) and the grilled salmon (well done) with the cauliflower side dish (me). And for dessert, we got the Nutella creme brulee and the bourbon poached pear with fig jam. Though I could try my husband's starter or entree because they had gluten in them, he loved both dishes. Mine were very good as well, even the salmon was very flavorful! The cornbread was an amazing treat since it's made in house and gluten free. Very attentive staff, busy kitchen making things fresh. Beautiful ambiance, but did get a bit noiser as more tables filled. We took a 5pm seating and were finished at around 645. We will absolutely return! Loved the seasonal ingredients and local foods from the Chesapeake watershed. UPDATE - We returned for brunch this past weekend and again, the food was excellent. I got the burrata salad (a delicious combo of flavors) and the eggs benedict (minus the English muffin since I'm gluten free). Absolutely yummy 😋 - 2 poached eggs with short rib meat with roasted potatoes and fresh hollandaise sauce ⭐⭐⭐⭐⭐ My mom had the crab cake sandwich with fries which she said was one of the best crab cakes she's had in the area and loaded full of fresh crab. My husband got the burger and felt it was really stellar with a cheese that added lots of flavor along with perfectly cooked bacon.”

“An absolutely world class dining experience in Chestertown. We had the scallops and pork belly, and the lamb three ways dish. Both were delicious, and the greens we shared for a side, although they weren't the eye candy that the mains were, tasted spectacular. Everyone we interacted with was friendly, professional, and laid back. Keep up the good work! PS, the cornbread was awesome.”

“Our second time here was just as wonderful as the first! Dining here is an experience in itself because you honestly forget that your in little ol’ Chestertown! The atmosphere is both classy and relaxing. The food is simply incredible, and the dessert…phenomenal! The talent in that kitchen is undeniable. I want to make sure I compliment the waitstaff as well. They were all so well mannered, prepared, and well trained. You can tell everyone there takes pride in their job and they truly want you to enjoy your time there. We are already looking forward to our next visit!”