This place was a bit confusing at first because it has two different entrances--one for the bar and one for the restaurant. We started on the bar side, which was extremely busy and we couldn't find a seat for about 30 minutes. The only downside is that seating is first come, first serve, so you end up hovering around tables waiting for people to leave, which wasn't ideal. We eventually got frustrated and went next door. Even though they're separate, the bar and restaurant are connected, so you can easily walk between the two. We ended up having an amazing meal at the restaurant side, so it was definitely worth switching over. I highly recommend the lobster roll. I'm giving 4 stars mainly because of the experience on the bar side. read more

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I was super excited to try this place, but was honestly a bit disappointed with how it turned out. For starters, it was extremely loud, and it was pretty hard to hear the people I was sitting with. Additionally, the bathroom was dirty and tiny. And finally, the my food wasn't great. I ordered a chicken Caesar wrap, and was super disappointed. The wrap was too wet, the chicken had no seasoning and was ice cold, and the lettuce was extremely moist and slimy. It just didn't taste fresh. Also very little Caesar dressing. The only good thing in my meal were the fries and the pickle. I will say, however, the service was pretty good. Our waitress was super nice and got our food out quickly despite it being packed. They also had a bingo game going which was cool. I would come here for fries and drinks, but not really for the food. read more

Chatham Squire Restaurant & Tavern - New American Near Me - Chatham, Massachusetts

I am such a pain when it comes to Irish Pubs. When they are good, they are GREAT and when they are bad, they really stink (Auld Triangle food in Hyannis is a huge miss in my book unfortunately). On our Chatham food tour, 3 generously portioned and perfectly executed fish tacos that really made us happy local tourists! Looking at the menu, prices are not as scary as you may expect from tourist trapping Chatham main street, and judging by other diners - you get a lot of grub for your dead presidents or playful plastic. Lovely staff, great vibes. Good times! read more

What a great time with family! We came the weekend of the fourth and had a blast! Kylie was our server and was so attentive and kind! Also fun fact my parents met here back in 1996, what a fun memory to return to together! read more

I loved our visit here. I had see a lot of tiktoks recommending this spot and I can see why. It has some vintage charm, like it's been a staple for locals and tourists alike. We were sat as a patry of 5 fairly quickly and good service from our server. We tried a couple local brews and everyone ordered their respective dishes. I tried the lobster bisque and pesto chicken sandwich. It was excellent! The bisque was creamy and had a fair amount of lobster. The chicken was a little different as it wasn't a breast but chunks of chicken, maybe also used in salads? Overall, it's a little "grungy" but has that taver/pub vibe. I would love to come back again. read more

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Retro tavern ambience and very good food. We had no issues with the service and were seated right away despite having eight people.

Waited a long time (over 20 yrs) to come back to this establishment tonight! We're at the CB Inn down the street and couldn't leave tomorrow without enjoying their fresh scallops. I ordered them for take out and waited over 25 minutes. Got them as soon as they came out of the kitchen, drove 2 minutes back to the hotel and the dish was cold. The "mushroom" risotto had an overtone of fish (perhaps made with a fish broth-overall unpleasant taste) and was complete mush. The scallops weren't cooked at all and therefor rubbery. The asparagus was cooked perfectly, had a beautiful char and was actually warm. $40 for 6 broccoli spears is a huge disappointment though. Sorry Squire... next time I'll have go for the clams! read more

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People will spike your drink here. Be careful!! Tiki Bar next door is a great alternative!!

The Chatham Squire - Chatham, MA Rating: 1 out of 5 The Chatham Squire has a long history--over 50 years as a local favorite on Main Street. It's known for its casual, rustic tavern vibe and its reputation as a community hangout. But my visit didn't live up to the hype. We ordered: * Fish and chips - average, nothing special. * Fish taco - dry, flavorless, and honestly one of the worst I've had. It needed lemon, garnishes, anything to give it life. Even the salsa didn't help. * Clam chowder - just okay, but not worth coming back for. The atmosphere was lively, and our server did her job. But the host--a tall man at the entrance--was rude and cold. Not welcoming at all. It immediately set the tone for the rest of the visit. I came here expecting a solid seafood spot, maybe even a surprise hit. But this felt like a tourist trap. The food lacked flavor, the vibe wasn't friendly, and even the promise of a coffee place nearby turned out to be nothing. I eat out a lot, and this isn't it. Chatham has much better dining options. Skip the Squire read more

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What an adorable spot.. if you want a true pub feel, this is the spot to go. We had 4 adults and two kids with us, and they offered coloring pages for the kids which is always appreciated. The food did take a while so I would suggest ordering quickly if its busy (which it was when we were there). The clam chowder was excellent, as well as their burgers and fries. Whenever we are back in the Cape we will definitely be stopping in again! (hot tip: For any Squire swag.. go to the specific Squire storefront across the street!) read more

Chatham Squire Restaurant & Tavern - New American Near Me - Chatham, Massachusetts

I love places like "The Squire" so much. You have an immediate feel of belonging. I can name 10 other bars/pubs where I feel the same way. We sat at the bar which is at the center of the "bar side" of the restaurant. Seating all around the bar itself and seating at a shelf/bar along one side. A couple of TVs had a game on. The walls are covered in signs and license plates from all around. Can you find the bears? Drinks were good. Painkiller for me, Cape Cod Margarita for my wife. We were snacking our way around so we just grabbed the Nachos. We could have shared them with two more people and probably still not finish them. Bar tender was great, engaging everyone around the bar. The place was busy, but they kept up nicely. High tops in the back and a pool table off to one side created a little something for everyone. A must stop anytime I'm in Chatham. read more

Chatham Squire Restaurant & Tavern - License plates cover the walls. Was this one from a Porsche owner! IYKYK. - New American Near Me - Chatham, Massachusetts

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Place was absolutely disgusting...urine all over the bathrooms, food was bad, service worse, and the frat kids working the door on Sat. May 30th made a racist comment to one of our party members. They even proceeded to giggle about it to themselves afterwards. Avoid this place at all costs. 0/5 read more

Can definitely see why this place is such an institution. Bartenders are super friendly and have a heavy pour. Drinks aren't stupidly priced. You could spend hours looking at everything on the wall. There's also a bunch of bras hanging up in the back which is somehow very captivating. Worth stopping in. read more

Chatham Squire Restaurant & Tavern - bras:) - New American Near Me - Chatham, Massachusetts

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Apparently a local mainstay. Fun bar and atmosphere with an array of memorabilia everywhere. We stopped in for a snack specially for their famous Costello - half chowder and half bisque - soup. It was solid. We also had a Caprese salad which was a special and it was fine. Service was on point. read more

Chatham Squire Restaurant & Tavern - New American Near Me - Chatham, Massachusetts

Great little tavern! The food was fresh (fried calamari, fish tacos, chowder and lobster bisque. Service was fast! Drinks were amazing!! Ambiance was great! Highly recommend this place. read more

I didn't come here with high expectations for the food, but we planned on some light snacking and just enjoying the seafood while at the Cape and some place that was casual so we could bring our unpredictable 11 month old baby with us. They do offer a kids menu and coloring pages for kids! Our baby prefer to eat the crayons and rip up the coloring pages but for more civilized children it would be fun and entertaining for a short period. So we got the mussels (got a white wine sauce with it per our waitresses suggestion) delicious, the mussels were nice and plump! The chowder was also decent, the raw sampler was a great deal! The fish tacos were disappointing, the tortillas did not hold up at all, ended up eating it was a fork. The wings were also a little too fried and the flavor a tad too salty for our liking. But the wait staff were all so friendly and attentive, A+ for service. read more

Chatham Squire Restaurant & Tavern - Approved of the shrimps - New American Near Me - Chatham, Massachusetts

Food was ok, service was efficient, seating was cramped, and music was loud. We wanted to give the place a shot because people say it's a must, but it was underwhelming. Bar on one side, restaurant in the other. Prices weren't bad considering the location, and seafood tasted fresh. The fries were a big hit. read more

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I felt dirty just being in there. Bathroom was icky. Food wasn't anything great at all. Burger and fries. I hope to not go back. Waitress was nice. read more

We had such a fun time at this old bar.. our bartender made some fabulous cocktails and was witty and fast moving. We spent a little over an hour there and had alot to talk about just with our surroundings. Look forward to coming back ;-) read more

This place used to be iconic. Fantastic food, and portions that would blow you away. Great local hangout. Reasonably priced t-shirts, etc. The owners retired. the new owners have destroyed the food, reputation and prices. Started a store across the street for merch that is hugely overpriced. The food is not great, comes not very hot, and you feel like cattle...just eat and pay your bill. The old staff had been there for years. We had people that we wanted to see each year. Now the staff could care less about you. I have been told most locals do not go there anymore. Just a heads up. They are riding the coat tails of the name and the old owners and staff. read more

Chatham Squire is one of those spots that while in Chatham you need to check out! Right downtown, this lively spot serves up seafood and drinks. We were lucky enough to find a spot at the bar and our bartenders were so helpful! We got a chicken Cesar wrap which was solid! Fries were crispy and perfect. Oysters were local and fresh. This is a fun spot for sure! read more

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Food wasn't that great, found some mud/sand inside my linguine and clams pasta and it was really bland. The kitchen remade our food, but it was really salty... honestly wish i just received a discount on our check. On the flip side, our server Daniel was very sweet and attentive. read more

Chatham Squire Restaurant & Tavern - New American Near Me - Chatham, Massachusetts

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A Chatham institution, the heart of the town, and the French Dip is the best sandwich I may have ever had. Great bartenders, lively and classic atmosphere, live music, trivia nights, fun crowd. My family has been coming here for generations, and I'm so glad we're able to keep the tradition going. Expect a large very crowd during the summer nights and weekends. Best to go at an "off hour" like 3pm. read more

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Everything from beginning to end was really excellent. We had a great lunch starting with best steamers we ever Had so fresh and finished with two amazing huge hot lobster rolls. The service was really outstanding we had a great server named Madeleine. Hard to believe the ratings aren't much much higher for this restaurant as all the food that went by looked really amazing; especially all the fried seafood. We'll go back again next summer. read more

Chatham Squire Restaurant & Tavern - Best hot lobster roll I ever had. Fries were so crispy. - New American Near Me - Chatham, Massachusetts

We stopped in here on vacation with a huge group and we were seated immediately! The service was so kind and accommodating, they happily offered to take a group photo. The ambiance was fun and cool, loved the interior. There's a pool table, and a separate "chiller" dining room if you aren't in a bar mood. There's so many food options and some that are specifically regional, oysters, quahog, etc. The calamari was fresh and tender and I loved the chipotle aioli. I'd love to come back here later at night or to try some different menu items. read more

Chatham Squire Restaurant & Tavern - Calamari and fries - New American Near Me - Chatham, Massachusetts

The Squire is the classic spot you have to visit on your trip to Chatham. I've been coming here for a decade, and nothing has changed. That's the way I like it, and that's the way most people like it. We ordered some clams on the half shell, and the mates plate. It was a combo of fried scallops, shrimp, cod, and calamari. An important note for all your gluten-free friends, their fried seafood is completely gluten-free! I've never seen this before in a restaurant. I wish I could say the gluten-free was just as good, it was really good, but with gluten is better. The gluten-free breading came off very crumbly, making it a bit hard to eat. This isn't a culinary landmark, but it's a super fun place to have drinks in Chatham. Definitely make your way here and stop for a mudslide and lobster bisque. read more

Chatham Squire Restaurant & Tavern - New American Near Me - Chatham, Massachusetts

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The Squire is a fun place to gather with friends for drinks. The food is variable, probably depends who is cooking in back. Recently my sister and I grabbed lunch there. She had a salmon poke bowl that looked and tasted great. I ordered nachos, which, according to the menu were to be served with cheese, beans, corn, jalapeños and pico de gallo. Because they were coming with pico de gallo instead of typical salsa, I selected the nachos. What a huge disappointment to receive my plate of nachos covered in pedestrian, bottled mild salsa turning my chips all soggy. If you say the dish is made with pico de gallo, you better deliver pico de gallo. The salsa was like some BS, generic jared crap one would pick up at the grocery store. Our server was very pleasant and attentive. He did make the overall lunch experience good. . The chips were good and there was plenty of gooey melted cheese. They fell VERY short in delivering what was described on the menu. The nachos were supposedly served with pico de gallo. The pico de gallo was the deciding factor in my choice, well what was glopped on was crappy bottled mild salsa. What a major disappointment. If a restaurant says a menu item is served in a particular way or specific sides, it better be served that way. read more

I had heard the Squire was "an institution" and figured it was a must on our visit to Chatham. I felt somewhat disappointed as the restaurant felt dirty and the food was overpriced for what it was. I personally had the hot lobster roll and pretty much was afraid to get another the whole time on the cape because it was that mid. Also wanted to note that previous menu pics on yelp showed upper 20s for price of this yet it ended up nearing $50! This did seem fairly standard pricing as we continued our cape travels though, yet somewhat more than other places. I tasted the crab cake sandwich my family had which was okay. I've had better. This place seemed to be more novelty than tasty- but I can say I've been! read more

Chatham Squire Restaurant & Tavern - Menu - New American Near Me - Chatham, Massachusetts

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Walking downtown Chatham while visiting with friends and stopped in for apps and drinks. We did have a bigger party with four children. The kids meals came out quickly, which we appreciated but it took a while for us to get high chairs that we requested. Our waitress was good but did not check in very often. Food was okay, I expected more from a local place. We ordered the Buffalo chicken tenders, which were very spicy (so you have been warned) the Brie, fair at most I have made better Brie dips at home, coconut shrimp and the nachos with chicken which was the best out of everything! The chicken was flavorful and toppings pulled high! The kids chicken tenders were a good portion. The best part of the meal were the drinks, espresso martini and mudslides were amazing! Space was loud and crowded. If I were walking around this wouldn't be the first place I would choose but it also wouldn't be the last. read more

Had an excellent night in the early summer season at the Squire! Stopped in for a Tuesday night trivia night and had an absolutely blast. Trivia master was witty, responsive, and an excellent host all around! The service was quick and friendly, and the drinks were surprisingly delicious! For a beachy bar, the margaritas were absolutely perfect! Fresh and served with a lime and salt rim! Also tried the bluefish plate with caper berries, tomatoes, biting red onion, and a delicious creamy dill spread. Truly the perfect bar snack! read more

Chatham Squire Restaurant & Tavern - Bluefish plate - New American Near Me - Chatham, Massachusetts

I would have loved to be able to assess the food here. However, the only thing I can tell you about is the service. We were seated right away for lunch, and that is the best part because a server never came to greet us or take a drink order or anything. We sat there for 20+ minutes and nothing. I can't even say they were packed as there were multiple tables empty. We saw two other groups be seated and get drink orders right away. So as much as this place was recommended to us, I give it a big fat 0. Trust the reviews people. This place is overrated. So many other restaurants with great service and great food. Don't waste your time or money here! read more

Quiet cold Sunday night visiting Chatham for a quick getaway and decided to go to the Squire. We've been here many times but tonight was special - the Rose Clancy band, a group of local musicians plays an Irish music session. on Sunday nights. They are so talented. Combine that with really good food, nice service and the pubby atmosphere, and you've got a truly enjoyable evening! read more

So sad to see this favorite go down hill. Yesterday, we gave it another try. We waited for 15 minutes while the hostess stood there not seating us. She was waiting for someone to clean the tables. But could not explain why she could not go and get help. I spoke to a waitress and she said, "yeah, someone is coming." You can't make this up. The food has also gone downhill. It's just another sad story of a legendary place that has been ruined. Avoid. read more

A Chatham icon since 1968, the Chatham Squire is a must-visit when you find yourself on the elbow of Cape Cod! This place is charming, not 1 square inch of the walls and ceiling are not decorated with some sort of sign, patch, sticker etc. and you know that everyone who walked through this door has a memorable story of their time there. Whether you visit for a drink, their New England fare, live music or just to experience the local culture, you can't miss the Squire! & what better beer to order than one brewed less than 11 miles away by Devils Purse Brewing, the Squire Lager is an American Lager that is crisp, drinkable and refreshing with a tinge of natural sea salt (or maybe that was just in the Cape air)... read more

Chatham Squire Restaurant & Tavern - New American Near Me - Chatham, Massachusetts

Happy to have had a late lunch here in the off season. Great service, delicious clam chowder, chicken Caesar wrap, tuna poke bowl, crab cake sandwich etc. Lively bar scene. read more

We loved this place. This was our first visit to Chatham, and our friend and host had enthusiastically recommended it. The clam chowder was arguably the best I've had, and the rest of the seafood feast was great-- shrimp and calamari appetizers, and fish and chips with a deftly poured Guinness. Our server, Maya, was superb; she went out of her way to make our evening welcoming and fun. read more

The Squire was recommended to us from many locals and we are so happy we checked it out. It is everything you want in a dive bar; tons of character and great drinks! My mom and I sat at one of the cocktail tables by the bar. The service was quick and efficient. We only got drinks, but the bar food looked great! I had the Cape Cod margarita, which was super refreshing! I loved the pink color and I'd definitely get it again. I can't wait to come here again next time I'm in Chatham! read more

Chatham Squire Restaurant & Tavern - Cape Cod Margarita - New American Near Me - Chatham, Massachusetts

This was the perfect place to stop in for a quick bite and a drink or two on a warm summer day. While here we drank some painkillers, and ordered a few seafood classics. Of course it is a little touristy but I don't blame them at all you need to conform to the masses. The service was great, it was fun, and made a great start to our cape cod vacation! read more

Chatham Squire Restaurant & Tavern - Pain killer - New American Near Me - Chatham, Massachusetts

I've visited The Squire for decades to get a taste of their always-good Lobster Bisque. I once again found it to be delicious on our last visit (5/12/25). This time I brought my relatives and we had a big lunch. Everyone loved their bisque, and the Caesar salads. However, my buffalo tenders were lackluster, and strangely, had an overpowering dill flavor in the sauce. My brother's fish sandwich was mediocre at best. Too much bun--not enough fish--a "fish stick on an oversized bun." Two of us added chicken to their Caesar salads and regretted spending the extra money to do so as the chicken was dry, overcooked and flavorless. read more

$26 for fried clams that consisted of about 12 clams! HARD PASS you can do much better at other places. Total trap.