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    Simon's Marketplace

    4.2 (110 reviews)
    Closed 8:00 am - 6:00 pm

    Simon's Marketplace Photos

    SIMON'S MARKETPLACE ATMOSPHERE

    What's the vibe?
    Casual
    Moderate noise
    Outdoor seating
    Good for kids

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    Recommended Reviews - Simon's Marketplace

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    Jenn H.

    This is a cute town with some nice shops. I started my day with breakfast here. You can get a lunch sandwich or breakfast foods. I got a bagel with smoked salmon and cream cheese and capers. They hadn't changed the menu board of specials so I was a little disappointed when I saw listed but couldn't have the Cuban sandwich. Luckily, I enjoyed what I got. My mom went with a simple grilled cheese. We shared a sugar cookie. There's also lots of gift and decor items to shop. Service was friendly and it feels like a warm, local spot where you go weekly to meet up with a friend, have some lunch while reading a book, or grab a coffee and sit outside. The lunch specials looked and sounded tasty. If you're in the area or looking for a nice day trip, check out Chester and start the day here. Maybe get some sandwiches to bring to Gillette Castle which is nearby.

    Bonnie G.

    Obsessed with this place. Every dish is healthy, hearty, and home cooked, like you're in a friend's kitchen. The sweet-and-savory Mayflower "Thanksgiving" sandwich, the meatloaf, the brussels sprouts, the creamy mushroom barley soup, the cowboy "kitchen sink" cookies. Includes an adorable boutique for candle/stationary/creams shopping. Sunlit, calm, lots of windows, peaceful. 5 stars!!!

    Megan K.

    It's an interesting vibe in here for sure. Some of the staff working were super nice, like the person who went and got me ice to change my super hot coffee that burned my tongue into an iced coffee because I obviously couldn't handle it. Then there were a few others working who really could use a bit of interpersonal communication skills training, honestly. My s'mores latte was delish, once I could feel my tongue again. The PB cookie I got was also pretty yummy. There's lots of cute random gifts for people that can be found in here, as well as holiday cards.

    Stuffed Puff Pastry with Chicken and Mushrooms
    Lindsay N.

    The center of downtown Chester is truly a treasure trove and Simon's Market is one of its gems. From fresh coffee and baked goods to prepared hot meals and desserts, Simon's Market is the place to fuel up. We popped in for a warm coffee during the Tractor Parade and were surprised how spacious it was. From the outside, it only looked to be a small cafe. A wave of coffee aromas hits you when walking through their door. There was a self serve hot coffee bar and coffee bean dispensers with grinder, serving up a variety of Jim's Organic Coffee. Seating is set up in front, followed by a counter serving up specialty coffee drinks, cookies, muffins and breads. When you walk further into the shop, there is another counter with warm meals for lunch specials, prepared food and desserts. The wall opposite from counters are lined shelving, stocked with Chester souvenirs, gifts, party supplies, greeting cards and other trinkets. Simon's Market had so much to offer, it's crazy that was our first time visiting. We got a few coffees; Americano, Dirty Chai and a staff favorite Tiramisu Latte. We tried a hot meal lunch that was a savory stuffed puff pastry with chicken and mushrooms. It came with a small side salad and slice of bread. The puff pastry was buttery and flaky, chicken was moist and the mushrooms were full of flavor. We also grabbed a few cookies and a baguette for later.

    Inside view of counter
    Jon L.

    Cute little Deli with a nice variety of vegetarian sandwiches. We got a caprese on a baguette and a roasted veggie sandwich with spinach, artichoke and feta. It's a "counter-service" place with a small table area. The restaurant is in a cute town on a quaint block with a lot of nice shops, restaurants and galleries to walk around and shop at.

    Audrey C.

    My boyfriend and I stopped here for some breakfast and had a great experience. The food was delicious, the iced coffee and latte was so so good, and the employees were so sweet. I would for sure come here again!

    Caprese - yummm!
    Sarah S.

    Another delish lunch at Simon's Marketplace! The staff are always super friendly and the food is fresh and crave-worthy. I had the Caprese and my husband chose the Boom Roasted. Our daughter gave two thumbs up to the cookie and the salted baguette. We live about 45 mins away but always stop at Simon's when we're in Chester. PS We miss The Blue Oar!

    Dirty Table.
    Kirk C.

    Ok, I thought long and hard regarding this review. This review is actually based on 4 meals over 3 days with 3 actual visits to the shop. I am hoping this is a wake up call to the owners, or at least the managers. First meal, (drove over from Ivoryton) I ordered an egg sandwich for myself, and as I was waiting I noticed some guy with glasses in the back room, coming out and grabbing ingredients to make something, I noticed he kept touching his face, then his glasses, then i noticed he grabbed a tomato from out front for the sandwich he was making. It wasn't until I finished eating, i realized he was the one who made my sandwich, not the lady who was at the sandwich counter earlier, so I got a little grossed out. needless to say. ( If you are touching food, wear gloves! ) 2nd Meal As I was leaving Simon's, my wife called and asked if i could bring her a turkey sandwich, so i ordered it. As the lady was making my wife's sandwich, she answered the phone a couple of times, as they were busy. Once again it didn't dawn on me til later that night, this woman never changed gloves after touching the phone that multiple people had touched throughout the day. I gave my wife the sandwich, I checked in with her and asked her how the sandwich was. She said the bread was stale, and tasteless and proceeds to open the sandwich, and there is no turkey on it! So being annoyed I had her take a picture of the other half, and I brought it back to Simon's, and the girl behind the counter was apologetic and gave me a new sandwich no questions asked. 3 & 4th Meals My wife and I were going to go to the Villager in Chester for a late breakfast, sadly it was too late when we got there, so we said "lets give Simon's another chance". My wife ordered a different turkey sandwich, on a different bread, I ordered a BLT, well once again my wife's bread was stale, she said the turkey was fine. Well, my sandwich was dry, chewy, they didn't cook the bacon enough, so i had to pull my sandwich apart, after each bite. Bread is key, you might want to switch your bread company, as I saw some other reviews that have said the same thing... Now for the inside, there was no A/C, they have a window unit in the back where you pay, and you have to stand on top of it if you want to feel any coolness, and they have a walk in entry rug that was filthy, as if it hadn't been vacuumed in days. The garbage is piled up overflowing, and surprisingly for such a liberal town there was no recycle bin, You need bigger trash bins. ( see pics) Someone who worked there left an uncovered coffee carrier ( see pics), which i am sure is against health regulations. My table was filthy, and my shirt stuck to the back of the seat, ( window seat on the right looking out on to Chester streets) and lastly I was in there for at least 30 mins, people coming and going, and not once did I see anyone walk around and clear off the tables, in fact, as I was walking to the trash bin, i took garbage off 2 tables myself. You can look at my reviews, i don't give bad reviews, and I hate to do it to this one now, but the owners need to close for a day, and deep clean this place. It is a really cute store, and the young people working there were very nice, it just needs some love and attention.

    Brussels sprouts
    Jenni F.

    This place had a lot of cool elements. There was a coffee and pasty bar as well as a lunch counter for sandwiches and prepared food items (like the Brussels sprouts I ordered). The vibe was very eclectic and slightly chaotic. In addition to the food counter, the marketplace also have candles, stoneware, and such creating a gift shop feel. Of the food we ordered, my husbands curry chicken salad wrap was the standout. It was so flavorful and had just the right level of moisture for chicken salad! The item I would not recommend was the strawberry scone, it was far too bland for my taste. I would go back but would definitely want to try some different items from the large and varied menu. I also think I will go in warmer weather and sit outside as that seems like it might be a bit more relaxing.

    Inside entrance with lots of goodies to browse

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    10 months ago

    The oatmeal is SO good! A great place to sit and enjoy coffee and a muffin too. Simons is a great gathering place.

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    2 years ago

    Great sandwiches in a cute shop in downtown Chester. They also have prepared hot food and some party favors and other small gifts.

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    2 years ago

    Fantastic food, great service, and a super cute space to eat and enjoy as well. We love Simons!

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    The Anchor

    The Anchor

    4.9(36 reviews)
    1.0 mi

    I am actively reviewing it as I'm sitting here enjoying a delicious Monte Cristo with my wife!…read moreWe're devouring it because it's so delicious! Here's a tip, get your own, don't do splitzies like we did. I also had a dirt bomb to start with my Americano. The two definitely complimented one another so when in doubt, just go for it. The owner threw it in on the house because we kept mulling it over. This place is cute & quaint & located right at the marina. The customer service was top tier and the in house baked goods are to die for! They are cash only but there is an option to pay through venmo. This is definitely a locals spot. Great gem so stop in!

    My family and I enjoyed a delicious meal at The Anchor in Chester, CT. Very good selection of…read morecomfort food. We had the Cubano (perfection), the veggie burger (fresh and flavorful), and the pulled pork mac and cheese (enough for my teenage son to eat with leftovers). The French fries were hot, crispy, and perfectly salted. Service was very fast. We decided to get some cookies for dessert later. The selection was eclectic, and they were all so tempting that we got several of them. Each cookie was wonderful, and they were still fresh when we finished them the next day. The restaurant was spotless and the staff was friendly, helpful, and welcoming. The Anchor also had games available for customers to play while in the restaurant, and doggie treats for the pups. Overall, a thoughtful and comfortable place. We will be back!

    Photos
    The Anchor - Fishing lure light fixture

    Fishing lure light fixture

    The Anchor - Cranberry clementine muffin

    Cranberry clementine muffin

    The Anchor - Interior

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    Interior

    Rusty Rail Tavern - The Valley Hot Dogs

    Rusty Rail Tavern

    4.1(51 reviews)
    2.7 mi

    I love the atmosphere food is decent I hate the fact that your kitchen closes like an hour before…read moreyou close. If your kitchen is going to close an hour before you close just say that's when you close.

    This small tavern, located in a barn, was right along our 'avoid highways' route. The building is…read moreset back from the road with a large gravel parking lot. They have a good amount of outdoor seating to the right of the entrance. Inside is a small bar with about eight seats (didn't count) and several high tops. There is also a loft with more seating overhead. We walked up a few steps to enter the building from the parking lot. I'm not sure if the side entrance also has steps so if you have mobility needs, call ahead to check. We sat at the bar and as it was a hot day, I asked for a water before ordering a drink. The water was refilled several times during our visit without my needing to ask. I really appreciate that! The bartender seems to be the owner from the way he was talking and let us know they have live music two night a week plus some nights they offer a special menu like Prime rib night or dogs eat free night. Yes, besides the kids menu, they have a menu for your pup. The interior is very much a barn, with lots of fun, metal signs and train memorabilia all around. Two TV's were on in the front corners of the room so you may be able to watch your game (golf the day we went) but it's not really set up as a sports bar. There is one fair sized restroom for everyone that is clean and locks with a hook and eye latch. They have a good size drinks menu which includes a variety of cocktails, a selection of draft and bottled beers and wine. The bar has quite a collection of whiskeys and tequila's. A separate menu is available for their pub fare foods. The menu is very well crafted. Lots of chicken options, sandwiches and wraps, burgers, hotdogs and salads. My SO got the spicy chicken sandwich. When asked, our bartender let him know it was spicy, but not too spicy and they have hot sauce behind the bar if he wants more heat. Which of course he did. He enjoyed the sandwich; crispy chicken, tasty sauce, fresh veg and bread. Messy to hold, after using several napkins he finished it off w/his knife and fork. Table ware set on the bar after ordering is in small paper sacks. I went for a burger. The patty is quite large, cooked to order and juicy. Fresh veg on there, soft bread and tasty. I enjoyed this burger and it was large enough I almost couldn't finish it. I opted for a side salad (for an up charge) instead of fries. The salad is a good sized side, the veg were fresh and the dressing is on the side. I did try the fries that came with the chicken sandwich and those are really good fries. Fresh potato, crispy outside, fluffy inside, salted. Really good. This was an excellent stop. Chatted with some friendly locals and the barkeep. Had a beverage. Grabbed a tasty sandwich. We left stuffed and happy. What more could you ask.

    Photos
    Rusty Rail Tavern - Loft seating

    Loft seating

    Rusty Rail Tavern - Memphis Dog with fries

    Memphis Dog with fries

    Rusty Rail Tavern - Rusty Rail

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    Rusty Rail

    Marker 37 - Great raw bar

    Marker 37

    4.0(204 reviews)
    1.0 mi
    $$

    It's a Friday night and we're meeting up with some friends! One of them suggested Marker 37 for a…read morevariety of reasons and today, we're going to find out why! Here's how things went for me during my visit. Atmosphere/Appearance: Set right on the Connecticut River in Chester, CT connected to its own marina is this gem. Reservations are recommended especially in the summertime since THIS is the place where you wanna be. We were here in early April so things hadn't quite picked up, but at least the snow was gone and we didn't need to wear super heavy coats. The parking lot is massive so if it's busy you'll be walking for a minute before you get to the door. But once inside it's pretty modern, chill and relaxed. The decor isn't over-the-top. Everything is straight-edged and just... almost minimalistic. However, we sat in the patio area that was certainly heated so we could see the view of the water while the sun set. It was a wide-open setting and I'm very glad the restaurant didn't smash too many tables and chairs in there. Service: I can't remember who took care of us, but I don't remember having any issues throughout dinner. It was fairly slow so I didn't expect any hold-ups. Food/Drinks: I started off with an old-fashioned which was fine. Nothing crazy. Next up was a New England clam chowder which is perfectly seasoned and flavorful. Textures were good and so were the seasonings. Spot-on. For dinner I went with their Prime Rib! It came out perfectly medium-rare with a side of fingerling potatoes, grilled squash, au jus and horseradish sauce. It was good. Just... kinda not exciting. :-/ Maybe I should've gone the seafood route since we were on the water. But no matter. Value: Not too crazy here. It's a nice restaurant, but prices aren't out of control. You can totally come here to chill, have a drink and an app or a full-on family dinner and not be upset at the final bill. In conclusion I liked it here, just not enough to want to drive all the way out here again. Would I come back? Sure, if I were invited by friends and stuff, but I highly encourage you reading this to pay this place a visit and enjoy the views! Thank you for reading.

    Marker 37 is a hidden Chester gem! Right on the marina, the water and boat views were beautiful. We…read moreheaded there for a late dinner and it was perfect at sunset and was able to take some great pictures. Inside they had a live band with music which I thought was lovely but we decided to sit outdoors for the views instead. We sat down to and i started with the watermelon spritz to drink and it was refreshing and so pretty! It came with a flower on top and it tasted like summer in a glass. Since it was late I wanted something light to eat and found the scallops and succotash. They were absolutely exactly what I was looking for. The waitress was so kind and checked in multiple times during our dining experience. There was corn-hole and games along the water and extra picnic tables where you could extend your stay a while. The whole evening was so relaxing and I didn't feel rushed. But to be honest, The only thing that rushed us out was the beetles that came later at night, lol so just something to think about when eating outside by the water. Other than that, the evening was just what a summer night should be!

    Photos
    Marker 37 - Patio Interior

    Patio Interior

    Marker 37 - Army is here

    Army is here

    Marker 37 - Bar Area

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    Bar Area

    Brushmill by the Waterfall

    Brushmill by the Waterfall

    3.4(208 reviews)
    1.0 mi
    $$
    Locally owned & operated
    Locally sourced ingredients

    Great ambiance as you walk in by the waterfall. Three rooms depending upon the vibe you're looking…read morefor; dressy dining area, casual bar, or cozy informal den. We chose the latter in a corner window right by the falls. The service was outstanding. From the moment we arrived, to helping us find our seat, to our server helping us with the menu, to the manager coming over and talking with us to make sure everything was ok. I liked how the server first checked to see if we had any time restraints along with food allergies, etc. Speaking of the food. We started with the clam chowder and scallops. The chowder was the best I've ever had. Plenty of meat and seasoned perfectly. The scallops were amazing. The manager later told us that the scallops were the only thing that had been on the menu since day one. They tried to rotate them off once and the people went nuts. We moved on to the duck and salmon. Both were delicious. Sides were perfect as well. I'd love to write about dessert, but unfortunately, we were stuffed. They looked good, but that will have to wait until next time.

    I give it one star as we have gone here around a total of four or five times. Each is terrible for…read moreone reason or other. We would not have returned except for a gift certificate. This time, the waiters are very poorly trained not that I need perfect service For instance just when you are almost done with your soup do they come with pepper which I would have wanted from the start. They went to remove my drink when I had 3/4 inch left. My wife's risotto was really dry and overall tasteless. My burger as I was afraid to order seafood as they really messed that up in the past was soggy and really foul tasting. Not sure how you can ever mess up a burger. The location overlooking the river is nice, so many more better places around.

    Photos
    Brushmill by the Waterfall - Upstairs in the restaurant

    Upstairs in the restaurant

    Brushmill by the Waterfall
    Brushmill by the Waterfall - Delicious coffee martini

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    Delicious coffee martini

    Simon's Marketplace - breakfast_brunch - Updated July 2026

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