Watershed Alley - Chestertown

What an amazing dining experience! We recently celebrated our anniversary in Chestertown and the Watershed Alley was highly recommended. We certainly weren't disappointed! Our server was so nice and she made sure our experience was perfect.We had beef carpaccio and octopus for appetizers. The octopus was some of the best I've ever had- so tender! For dinner my wife had a strip steak and I tried the venison. They were both cooked to perfection and I don't think I've ever had venison that was as tender and tasty as this. We shared the brussel sprouts, and after trying them, I probably would have placed six more orders because they were so good.It was very busy, but it wasn't so loud that you couldn't hold a conversation. With that said, I would recommend making a reservation.Looking forward to making the trip back to Chestertown just so we can eat at the Watershed! Keep up the great work!

I 've been here 3 times so far and all three times I 've been blown away by the full experience. Amazing, delicious, highly creative and artful food utilizing a variety of proper local and seasonal ingredients to great advantage. Amazing service from staff who really care about you having a good time as a guest and are not only highly professional but also seem happy to be there! And perhaps most surprisingly, the pricing of such a high-level menu is kept very reasonable and accessible — much more affordable than any restaurant offering a remotely comparable experience in any nearby big-city dining scene. As someone who regularly seeks out fine-dining experiences everywhere I go, I can emphatically say (without blowing smoke) that Watershed is an absolute GEM not just of Chestertown but of the entire Mid-Atlantic region. For now, it 's a best kept secret of a small town, but if they keep up what they 're doing and continue to build upon it, I can easily see it becoming a destination in itself. Wouldn 't be surprised if these guys earn a Michelin Star in the next few years.

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.Dietary restrictions: Menu is well market what is gluten free or what could be made gluten free. Their house made cornbread is gluten free as well which is a really nice treat!

Had an absolutely outstanding experience. Food was fantastic and Sharon took exceptional care of us. Highly recommend!! And we will be back soon.

You couldn't have had a nicer and more attentive Waiter than Donald. He tended to every detail without fault. He even informed me of the Festival that will be in town next weekend and gave me a brochure. I had the Artisanal Cheese Board to start, then my entree was the 10 oz. Grilled NY Strip Steak medium well, with Mac N’ Cheese, all cooked to perfection! In addition they were two pieces of yummy Cornbread.Donald also informed me that upstairs there is a Banquet Hall for special occasions. Good to know! I recommend this place!Vegetarian options: I wasn't concerning myself with vegetarian cruising. But there were several options for people who shy away from meat.Parking: The place is obviously popular (for good reason) so you'll want to get there early so you can get a good parking spot.Kid-friendliness: I didn't happen to see any children there at the time I went, but I don't see any reason why they couldn't/wouldn't enjoy a yummy meal there.Wheelchair accessibility: There was plenty of space between the tables to maneuver a wheelchair.