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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.
Address and Contact Information
Address: 337 High St, Chestertown, MD 21620
Phone: (443) 282-9797
Website: http://www.thewatershedalley.com/
Menu Photos
Order and Reservations
Reservations: resy.com
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Related Web Results
Watershed Alley | Experience Gourmet Dining
337 High Street Chestertown, MD 21260 · Tues 4:30-8 · Wed–Sat 4:30pm–8pm · Tues–Sat 3pm–5pm · Wed – Sat 11:30am-2pm …
Watershed Alley | Chestertown MD – Facebook
No photo description available. Mark Henckel and 11 others · . 12 · . Watershed Alley. Feb 7 . . Sticky Date Pudding toffee sauce/chantilly cream/granola.
Watershed Alley – Main Street Chestertown
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 …
Reviews
Lisa Hammell
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!
… moreElaine Studley
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.
… moreJacob Arrow
My girlfriend and I spent New Year’s Eve dinner at Watershed Alley, and I can say it was an experience we will not forget. From the food, to the service, and finally the warm and inviting feel of the restaurant. We thoroughly enjoyed ourselves. Shout-out to the Manager James, he greeted us at our table, kept us laughing, and made us feel welcome even though it was our first time at the restaurant. We will definitely be back and highly recommend Watershed Alley to anyone looking for an upscale dining experience.
… moreAllan Leonard
I hope this message finds you well. I wanted to take a moment to share my thoughts about Watershed Alley Restaurant, which I recently had the pleasure of visiting. The ambiance was delightful, providing a warm and inviting atmosphere that made for a perfect dining experience. The menu offered a diverse selection of dishes, and I was particularly impressed with [mention any specific dish you enjoyed]. It was not only delicious but also beautifully presented. Additionally, the staff was attentive and friendly, ensuring that our needs were met throughout the meal. I appreciate the effort they put into creating a welcoming environment.
I highly recommend Watershed Alley to anyone looking for a great dining experience. I look forward to my next visit!
… moreI highly recommend Watershed Alley to anyone looking for a great dining experience. I look forward to my next visit!
Jennifer Fugo
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.
… moreWe 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.
Patrick Shoemaker
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.
… morePS, the cornbread was awesome.
Toni Lewis
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!
… moreLiz Shovlin
We love coming to Watershed for the fresh, local, creative food, atmosphere, and staff! Recently we were married and knew we had to enjoy catering from the best spot in town! Our wedding brunch was delicious, beautiful, fresh and convenient!! Watershed delivered to our venue in perfect packaging. Look at this lox platter! Rodney Lisa Donald Kyle Aiden Katie and the whole crew are so kind, welcoming, and talented…if you’re a foodie, a visitor, or heck even if you just need a bite to eat this is the place
… moreRick Abolt
Such an upscale eatery in a small town. This was a total surprise….
So, we showed up without a reservation (intentionally). They were full and couldn’t seat us. However, the person observing the new greeter stepped in and asked if we would be okay with sitting upstairs (being our first time here we were none the wiser.). This was at at 5:48 and were seated at 5:52. So we go to the 2nd level and find one of the cutest enclaves they could have offered. Our server asked what we would like and we inquired about happy hour. It was 6:02pm and he said that it ended at 6pm. I gave him the “SERIOUSLY!?!??!” look. He said yes. No problem! We order a bottle of the Pinot Bordeaux and moved on.
I will not bore you with the AMAZZZZZZING dinner and service we received, but it was just 5-star.
Look, I cannot begin to explain all of the reasons you need to visit this place in a google review. Just do it.
I see you Rodney! Thanks for an amazing experience. We will see you again soon!
Our server
… moreSo, we showed up without a reservation (intentionally). They were full and couldn’t seat us. However, the person observing the new greeter stepped in and asked if we would be okay with sitting upstairs (being our first time here we were none the wiser.). This was at at 5:48 and were seated at 5:52. So we go to the 2nd level and find one of the cutest enclaves they could have offered. Our server asked what we would like and we inquired about happy hour. It was 6:02pm and he said that it ended at 6pm. I gave him the “SERIOUSLY!?!??!” look. He said yes. No problem! We order a bottle of the Pinot Bordeaux and moved on.
I will not bore you with the AMAZZZZZZING dinner and service we received, but it was just 5-star.
Look, I cannot begin to explain all of the reasons you need to visit this place in a google review. Just do it.
I see you Rodney! Thanks for an amazing experience. We will see you again soon!
Our server
Kristen Jarvis
This place is a hidden gem in Chestertown. The chef and his team work hard to make creative, delicious food using local seafood and produce from area farms. The service is great and the ambience is very warm & inviting. It’s fine-dining but with an unpretentious feel. We went for a birthday & tried every dessert on the menu because they all looked too good to pass up! (Hats off to the pastry chef, Lisa). You must go here…you’ll be glad you did!
… more