My wife and I celebrated our 35th wedding anniversary at Watershed Alley this evening. Wow what an incredible surprise! The service was impeccable, the food was some of the best on the Eastern Shore. The waitress (Martha) was so attentive! We can't wait to bring more friends back with us. The presentation of the food was incredible. I wish there was a rating higher than 5 stars! These folks are doing everything right! Thank you for making our anniversary dinner so special! read more

The food, service, drinks, and ambiance are second to none. Sat at the bar for HH and then dinner - everything top notch. Don't miss this place! read more

Watershed Alley - New American Near Me - Chestertown, Maryland

Best restaurant in town. The chef came to my table to personally review my meal. Porkchop was excellent

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 second floor. It was a very intimate setting. The staff members are all so wonderful. They were patient with our questions about the menu and they kept the evening going in a seamless manner. They serve orange wine which is one of my faves! I was so happy to order it from the menu. The food was divine. I went with the seared tuna and the carrots as my side. Everything was INCREDIBLE. The chef also sent out a nice treat on the house. It was a delicious bite of curry goodness. The restaurant also has a private event space that my friends rented for the evening before their wedding. It was fantastic and amazing apps and desserts were provided and the experience of the entire evening was just amazing! My date got the roasted cauliflower and the duck. They were excellent as well! read more

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Had the most lovely Valentines dinner (on the 13th). Our reservations were on the early side, and we were promptly seated. Surprise! Turns out there was a limited price fixed menu. I had looked on social media and the website and had not seen any indication of that. We were greeted with glasses of prosecco (free) and the choices for our 3 courses were very nice. The fried oyster amuse bouche was delicious as was my rockfish. Our server Mia was great. The price fix was reasonable but wish we had known - I would not have spent time looking at the menu online! read more

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 last night with the crew. Our waitress, Mary, was very pleasant and the chef was able to adhere to my (many!) dietary restrictions. When I'm in a group setting, there's nothing I want more than to feel comfortable and this place went above and beyond. Thank you!! read more

Watershed Alley - Main dining room upon walking in - New American Near Me - Chestertown, Maryland

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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 go over and beyond for us (especially my mom) whenever we are there. The food is amazing the atmosphere has a casual yet chic vibe, the bar stools are a fan favorite here and the tables by the windows are too!!!! Whether you are local or visiting this a place you definitely want to try!!!! (I also heard the Red Acres Salad is a must ) read more

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My husband and I walked in there for brunch yesterday with no reservation (Mother's Day). It was late for brunch, around 2 p.m. and most of the other restaurants were closed. They took us in, made us very feel welcome and we had a most delicious brunch. It was a 3 course pre-fixe meal and one of the best. I had bibb salad, quiche and strawberry shortcake. My husband had the sausage, eggs benedict and a lemon sorbet. Chef's kiss! I highly recommend them. read more

Have been to this place once before for dinner. Good food. Tried to go for their Lunch which on their website says its from 11:30-2pm. Got there at 1:45pm and they would not seat our group. I believe the restaurant needs to update their website to state they will not seat you after a certain time. They should've honored their times. read more

Every person at this place wanted to do everything they could to make our visit enjoyable. From the time we figured out what door opened and got us in, to clarifying the three bathroom choices-every employee wanted to make a difference. Came here with 20 of my friends and they accommodated us flawlessly in an upstairs room. The restaurant was ready, the food came out quickly and was incredible. From the salmon on a bed of cut veggies, to the shrimp and pasta, the food was well made. Crab bisque had the right amount of high quality lump crab and was poured with panache. Crème brûlée dessert was also done exceptionally well. It helps to be in a space with creative artwork (oyster shell chandelier) and classical waterfowl and sea paintings. Food had some spice. Soup had some heat. Loved the flavors. read more

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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 while but overall loved it! The risotto was so surprisingly good!! read more

Quality in all aspect of food and presentation which drives one to return and experience new menu options. To date my three visits and dining at Watershed Alley has been awesome. Service on all occasions was great and added to a "I wanna come back to Watershed Alley ". read more

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Our 1st time visiting chester town, and therefore our first time here... let's just say we were blown away by the way the place , from cleanliness, to amazing service, and the food ohhh the food lets say we will be regulars at this place when we are in town!!and we have only tried their brunch menu items...Ii give this place 2 thumbs up and 5 stars!! Oh and the gluten free options are great for anyone with celiac! read more

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Exceeded expectations! Beautiful renovations, tastefully decorated with a relaxing atmosphere. Friendly engaging hostess at the door, wonderfully sweet and attentive wait staff. My husband had the trout and I had the amazing crab cakes. We were delighted! Complimentary cornbread. And for dessert, the best light chocolate mousse creation and Delicious decaf cappuccino. Oh, and beautiful bathrooms. I can't say enough about how we loved dining here and we cannot wait to return. Kudos to the chef!! read more

Watershed Alley - Sublime chocolate mousse dessert and delicious decaf cappuccino - New American Near Me - Chestertown, Maryland

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Until yesterday we've only been here for a few happy hours. HH drinks are half price and the food rotates around a bit but we tried most of the HH menu and everything is really good especially the burger, egg rolls, cheese plate, and spicy shrimp. Service is always attentive and very welcoming. However yesterday, we did the Thanksgiving dinner To Go (for 8) and I'm pretty sure we are done cooking turkey for ourselves ever again. First off, you select a pick up time and when you get there, it's a cross between a well oiled machine and a little family party. Complimentary sparkling wine and hot cider while you wait the few minutes while they assemble the order for you so it's hot as possible. Everyone is in a festive mood even though they are working hard on a holiday. We didn't really want to leave but the family was waiting for us. They help you carry it out to the car. The food was exceptional. The turkey was perfectly seasoned and succulent all the way through and looked beautiful like it should be on a magazine cover. Mashed potatoes were smooth and creamy. Gravy was amazing. Never had corn bread stuffing before but I'm a big fan now. The flourless chocolate cake, pumpkin pie...even the bread rolls were great. After the crowd left and we reheated leftovers for dinner, I think I was able to enjoy it even more. The kind of meal where you're sad that it's over. read more

Fabulous! This is a restaurant with a high end menu without a snooty vibe. The ambiance in the restaurant is beautiful; the service was fantastic (Martha was our server, and she was just fabulous). So that's twice I've said fabulous, now let's talk about the food. So, so delicious. I had the salmon, served over a fantastic bed of mashed potatoes with some sort of gravy that was just delicious. My husband had the short ribs, also delicious. We shared the carpaccio app, obviously before the mains, and it was also great. All in all, we will definitely be back. This is just a really fabulous restaurant in downtown Chestertown that I hope to visit frequently. Try it! You won't be disappointed. read more

First and foremost, you can bring your dog and sit in the cute alley. So that's amazing. Second time stopping by at Watershed. Can't say enough great things about this place! It's such a beautiful restaurant, whether you're looking for a charming place to dine with your friends and family, or a romantic night out with your partner. You're treated like family here, and the food is just *chefs kiss*! Seriously, the best food over the bay bridge...by FAR. Much love to the chef and kitchen team for sharing their love for food--you can tell there's so much thought, care, attention, and expertise with every meal. Really spectacular. Also sooo much love to the GM Kyle who was incredibly warm, kind, and treated us like long time friends. It's really special when you come to a restaurant and you're treated with so much love! Same goes for the host (whose name escapes me) and our server, Martha, who was so sweet and accommodating, giving us the best service I've had thus far on my trip. We're staying in the area and have been to a few restaurants already and we have not been treated so kindly, so to come here and have this experience really was a heartwarming time. Thank you to the watershed team for a beautiful night. Appreciate all of you! Such a gem! read more

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This was our first time here so we did lunch. The atmosphere and staff were excellent. The food was, at best, average. My wife ordered the lobster mac and cheese. It was served as almost a soup instead of a creamy mac and cheese. I ordered the blue catfish because it was one of the specials. Tasting the fish by itself, it was cook great but it was very bland. The beans and sauce it came with saved it. Another in our party ordered the salmon. When the plate arrived, all it was a 4 oz portion of salmon, nothing else. He said it tasted good but wanted something...anything to come with it. We will try it again for dinner. read more

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 had the pork belly appetizer and I had a biscuit and mushroom gravy. Both were delicious, but got cold too soon. If the plates were pre-warmed, it would have been a better experience. I had the rockfish, which was locally sourced and excellent. My husband had the duck breast, also very good. His cheesecake dessert was better than my gingerbread, which was a bit dry. Most of the reason I'm rating a 4 and not a 5 is that the staff is obviously well-trained and trying hard, but could use a bit better management. When you enter, there's a long bench behind the hostess stand, and it was junked up at the end with water bottles and other random stuff. Our waitress struggled with the ordering system and someone else finally came to close out our tab when she went MIA. So all in all very, very good, and we hope to return. With just a couple of tweaks, it could be great. read more

Horribly slow. Small portions. Uppity attitude. If you like being talked down to prior to an over priced meal this is your spot. But at least you'll feel important. This place is a joke. read more

Yeah the food really is all that. Chestertown is so lucky to have this restaurant. Yeah it's expensive but keep the tourists' dollars coming! (Not more than dc prices) read more

A true hidden gem in Chestertown... great dunks and gourmet level food service and ambiance. Highly recommend!

Last night 5 of us had dinner at Watershed Alley, I made the reservation about a month ago. We traveled from the Philadelphia suburbs to celebrate my 65th birthday. When I made reservations over the phone I had an incredibly helpful person go over the menu with me. I was told they frequently change the menu based on what's in season but they are extremely flexible and can accommodate almost anything. I mentioned dietary restrictions and salmon and filet mignon were 2 foods that were on the menu and worked for me, was told they were always available as simply grilled options....they were not. I could have removed the clams from one meal but that was it. Two guests ordered the Bison, it was unavailable. Another guest like myself wanted a simply grilled salmon also like I was told would be available. When choosing this restaurant I had sent the other couple the menu and explained I was told filet and salmon are always available. So two guests ordered another seafood dish, 3 of us unable to order what we wanted ordered the pasta...it was ok, not great. The waitress was very nice but had told us they could not do the simple grilled because it was very busy. We arrived on time and were greeted. The hostess was about to lead us to our table when another employee approached the hostess. Rather than lead us to our table we stood there for several minutes as the 2 went over seating chart and chit chat back and forth about seating. My thought was the hostess should have seated us and not subjected us to seating problems with other guests as the 5 of us stood there. I had 2 other restaurants I'd considered for my birthday dinner and should have gone with one of them. Nothing like having to settle on second choice menu choice for a special occasion! We had a fabulous breakfast at our bed and breakfast and decided to skip lunch so we could enjoy a fantastic dinner, I left hungry! The 2 guests who ordered fish had a different fish substituted. read more

My husband and I celebrated our 20th anniversary here, and we were exceptionally pleased! The ambience is tasteful and decorated with paintings from a local artist as well as gorgeous living edge tables. The staff was welcoming and friendly as well as attentive. And the drinks, food and desserts were absolutely wonderful! We enjoyed a fabulous burrata appetizer, a mussels special, a perfectly cooked tuna steak, and more. It was a very memorable evening - and we will be back! What a great addition to Chestertown!!! read more

Did not love my crab cake. Kinda dry and bland. My beet salad was good. And the key lime pie was outstanding. I think the kitchen was having a difficult night cause my simple request to change one of the sides got all mixed up. I'm willing to give them another try cause the atmosphere was very welcoming and diverse clientele which I appreciate. read more

Sunday brunch. Chicken and waffles and swordfish. Both meals just outstanding. My swordfish was one of the best I've had, 6oz, perfectly seared, accompanied by 3 bean salad, simple guacamole and sour cream, and paired oerfectly with a Ten Eyck Taildragger IPA. Gorgeous design, all custom banquettes, second floor with second bar for busy weekends. Worth the drive from Wilmington by itself, but cute town with boutique shoppes, other restaurants, coffee shops. read more

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I drove out here because Google information for the restaurant said they were open from 11:30-9:00 PM this past Saturday. They were not. My husband and I arrived at 2:15. A sign on the street said they were open for Happy Hour at 3 PM. So, we waited. At 3 PM, we walked into the restaurant. No one was there to greet us. We awkwardly stood in the center of the dining room while three individuals worked in the open kitchen. No one greeted us either, despite seeing us and making eye contact. Finally, the mixologist greeted us as we approached the bar, which seats 5, maybe six people. I immediately noticed that the hours of operation on the Happy Hour menu did not match the sign on the street, which did not match the hours listed on Google or their website. Noted, not a good sign. Five additional people walked in and sat at a table, and now the bartender was spread across the dining room---hosting, bartending, and taking any orders. Simultaneously, the head chef on duty decided it was the perfect time to host a business meeting at a dining table close to the bar to discuss next month's drink menu. He pulled the bartender away from "hosting, bartending, taking orders, checking on his customers" for at least 30 minutes while he provided feedback and dropped colorful F-bombs for emphasis. Interesting---and noted, again. The mixologist threw together some great drinks, and we ordered two Happy Hour plates---a cheese plate and chicken wings. Both were nothing to rave about. I drove from Chester, MD, to dine here, not go to their Happy Hour. However, the general experience and food were so lackluster that I no longer want to try this place for dinner. I love the idea of the rotating menu and an onhand mixologist. He was energetic and passionate about his craft, so I am giving this review two stars instead of one for him. Unfortunately, he is collateral damage from poor management. It's a missed opportunity, for sure. read more

Absolutely wonderful place with fantastic service and delicious food. They never cease to impress us with their personalized service, interesting menu and bar concoctions that are a feast to the eyes and appetite. Every meal is a memorable experience and is worth every penny. read more

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What a delightful, delicious dinner! My husband and I really enjoyed the ambiance, with beautiful and interesting art pieces and cool lighting. And the friendly staff served up especially FABULOUS flavorful dishes! Husband had the Tomato/Lobster salad and the Roasted Citrus Cured Arctic Char with beets--Wow! I was mesmerized by my fabulous chilled Melon Soup and Herb Crusted Icelandic Cod. I also enjoyed the Just Peachy mocktail and we both had the Bittersweet Chocolate Mousse Heart served with Raspberry sauce. Presentation of everything was lovely and so was our entire experience. We took a quick tour through the upstairs party rooms, too: great spaces for smaller private gatherings and for wedding receptions as well. Best to you, Watershed Alley! Thank you! read more

If there was an option of "golden stars" I would have given 5. This was our first visit to Watershed Alley for dinner. We have for years enjoyed the quaint town of Chestertown. Mainly to go crabbing as a family. This was a last minute trip and a last minute dinner at Watershed- we were in awe! Beautiful property, amazing art decorated the dining area. The music was also noticed, the crowd was our age - 50-66ish and the music was quietly 70's rock. And then the food arrived- our server was very informative, offered plenty of detail regarding our questions as we ordered. The fried green tomato w/sweet corn chow chow and the fried prosciutto! Come on! Husband had the pan seared sea scallops- quoting him- the best scallops I've had by far. I chose the grilled salmon, served in a large bowl in a light broth as not to take away from the beautiful 2 pieces of grilled salmon, the beans with the broth were so good yet delicate. To complete our meal, well, we love chocolate, the choice was easy. Dark chocolate Pistachio Pave- oh my. A nice treat to end the experience at Watershed Alley. Please give this gem in Chestertown a go, you will return as we will in the near future. read more

Watershed Alley - Alley entrance to Watershed - New American Near Me - Chestertown, Maryland

Had dinner the other night with my wife. What a wonderful surprise in chestertown . Beautiful Resteraunt with both elements of the eastern shore as well fine dining . The service was on point and I was amazed that that had just recently opened . Food was well thought Out and courses where both both beautiful and tasty . Very excited to visit here again this fall when menu rotates. Give it a try it was well worth it! read more

Great restuarant. Nice glass of champagne for anniversary. Amazing veal osso bucco. So tender so flavorful with amazing bone marrow. Saffron risotto on the side complemented it perfectly. Husband with rockfish. He loves it. Would absolutely return and soon ! read more

Watershed Alley - New American Near Me - Chestertown, Maryland

Our first visit to this new eatery now residing in the same location as the late and much loved Lemon Tree in Chestertown, MD. While they have a steep slope before them to gain the renown and respect of the former inhabitant I believe they are well on their way with a fresh, bright and upscale décor and service. From the octopus carpaccio to the gluten free dessert everything was perfectly prepared, plated and presented, as much a delight to the eye as the palate. Our table was in the front window of the establishment and we enjoyed interacting with the sidewalk strollers and showing off our menu selections. We will definitely be returning, and soon, although next time we will be bringing friends to introduce them to our new favorite place. read more

Watershed Alley - High Street as seen from the window table. - New American Near Me - Chestertown, Maryland

I was lucky enough to enjoy an amazing dining experience at the Watershed as part of my 30th birthday celebration. The Braised Pork Belly and Marinated Cherry Tomatoes melted in my mouth. Chestertown is lucky to have Chef Rodney and Lisa, and I can't wait to visit the Watershed again. read more

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Ok, seriously, I've been there now 3 times in a week. Love the food. Finally some chefs that create beautiful, local cuisine AND can plate beautifully as well. That's hard to find. Oh, and options for my pain in the *ss gluten issues. The servers are all very nice and very personable. Love the open kitchen concept. They update their menu often so keep that in mind when reading this review. Their mixologist Jackson is super sweet and makes some fun cocktails. I feel like we're good buddies. I've tasted the Cool As A Cucumber (rum drink), my husband ordered that one and it's like liquid candy. I've also tasted the Tall Ship (cognac drink), really nice to sip. My personal favorite was a Pear Gimlet. Not too sweet and a little bit of sour. We did their happy hour one day (really nice, high end food for a great price) and had their Tuna Poke, Artisanal Cheese Plate, and a few others that are no longer on the menu. For lunch I had the Red Acre's Local Bibb Salad, and a fresh soup of the day that was a cream of clam and potato soup. All were excellent. It's right on High Street in Historical Chestertown. The space is stunning. They put a lot of money into this renovation, and that kitchen! I just can't sing enough good praise for this one and can't wait to see what's on the menu next time. read more

Pleasant ambiance. Food is delicious, service is the best in town. Celebrating something or someone special? This is your go-to.

The food was excellent and diverse menu. Been for dinner and lunch. Enjoyed the atmosphere.

Very pleasant discovery in Chestertown. We went for lunch but I'll be returning back shortly for dinner. Pork Belly and Tuna Poke were great starters and very original. Salmon, Shrimp and Grits, Chicken and Waffles also were excellent. Owner came around and spoke to the table is a very good touch. Everything for the food, drinks, and interior has been very thought out. Food comes from locals. read more

Watershed Alley - Shrimp and Grits - New American Near Me - Chestertown, Maryland

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Outstanding food, service and ambiance. This place truly rivals the best of Baltimore and DC! Its now our favorite.

Awesome restaurant in chestertown! A hidden gem. Would go back for sure. The tuna poke was over the top as well as the salmon.