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Best Comfort Food Restaurants in Winchester

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33 restaurants available nearby

A photo of Five Horses Tavern - Davis Square restaurant
4.5
Awesome(996)
Price: Moderate
• Comfort food • Somerville
Booked 7 times today
Five Horses Tavern - Davis Square is a gem of American cuisine in the heart of Somerville. Known for its "modern American comfort food," the restaurant artfully blends tradition with innovation, using locally sourced ingredients that cater to a variety of dietary preferences. Guests rave about their elevated pub food, describing the pretzel as "amazing" and the brunch as the "best we’ve had for a while." With a diverse menu that includes standout dishes like huevos rancheros and breakfast pizzas, there's something for everyone. Coupled with an "exceptional" staff and a lively atmosphere, it promises a memorable dining experience for all.
A photo of Goodnight Johnny’s restaurant
4.5
Awesome(143)
Price: Moderate
• Comfort food • Burlington
Booked 9 times today
Goodnight Johnny’s in Burlington is a vibrant haven for lovers of authentic American cuisine and live music. Known for its "quality food, great presentation," and friendly atmosphere, this spot promises a memorable dining experience. Guests rave about the diverse menu, from the delectable classic chicken pot pie to the creative salads and unique wagyu hot dogs. The upbeat ambiance is complemented by top-notch live music, making it perfect for a "fun night of singing and dancing." With attentive service and a welcoming vibe, Goodnight Johnny’s is a "gem in the neighborhood" that brings the best of American dining and entertainment together.
A photo of Tavern in the Square - Burlington restaurant
4.6
Exceptional(1770)
Price: Moderate
• Comfort food • Burlington
Booked 55 times today
Tavern in the Square - Burlington is a delightful haven for Comfort Food enthusiasts, offering a menu that shines with authentic flavors and hearty dishes. Guests rave about "the best burger I've had in a long time" and "delicious Cornflake Fried Chicken Tenders" that are sure to satisfy any craving. The welcoming atmosphere is complemented by a dedicated staff who ensure that every visit is memorable, with reviews highlighting their "attentive and friendly service." Whether you're indulging in a classic Mac & Cheese or exploring their gluten-free options, this Burlington gem consistently delivers comforting and delectable meals that keep diners coming back for more.
A photo of Mothership Alewife restaurant
4.6
Exceptional(76)
Price: Moderate
• Comfort food • Cambridge
Mothership Alewife in Cambridge is a stellar choice for Cocktail Bar enthusiasts seeking a unique and delightful experience. Renowned for its "creative, tasty, and attractive cocktails," this neighborhood gem stands out with its expertly crafted beverages that are both innovative and delicious. The Jasmine tea cocktail is often hailed as "the best I've ever had," showcasing the bar's dedication to quality and originality. With a friendly and attentive staff, Mothership Alewife provides a warm and inviting atmosphere, perfect for gathering with friends or enjoying a solo evening at the bar. The combination of delicious cocktails and a welcoming vibe makes it a must-visit destination.
A photo of Town Tavern restaurant
4.5
Awesome(347)
Price: Moderate
• Comfort food • Arlington
Booked 8 times today
Town Tavern in Arlington is a premiere destination for authentic Gastro Pub cuisine, promising an unforgettable dining experience with its "scratch-made eclectic" dishes that elevate traditional tavern fare. Guests consistently rave about the "delicious food" and "inventive cocktails," highlighting the exceptional quality and creativity of the menu. The monthly specials add a whimsical touch, such as the Cracker Jack fried clams, ensuring each visit offers something new and exciting. With a cozy atmosphere and hospitable staff, Town Tavern is perfect for family celebrations or a casual night out. Its commitment to quality and service makes it a local gem in the heart of Arlington.
A photo of Hunter's restaurant
4.5
Awesome(295)
Price: Moderate
• Comfort food • South Boston
Booked 39 times today
Hunter's Kitchen + Bar in South Boston is a beacon of authentic American cuisine, specializing in exceptional Southern comfort food. Executive Chef Lambert Givens, praised as “one of the best chefs in Boston,” crafts standout dishes like signature gumbo and chicken & waffles that transport diners straight to the heart of the South. Guests rave about the "phenomenal" mac & cheese and "to die for" cornbread, attesting to the restaurant's culinary prowess. The inviting atmosphere, infused with live music, makes every visit a memorable experience. Hunter's is the perfect spot for anyone seeking genuine American flavors with a Southern twist.
A photo of Buttermilk & Bourbon restaurant
4.6
Exceptional(3482)
Price: Moderate
• Comfort food • Back Bay
Booked 104 times today
Buttermilk & Bourbon in Back Bay, Boston, offers an exceptional Tapas/Small Plates dining experience that stands out for its authentic New Orleans and Southern-inspired dishes. Diners rave about the "phenomenal New Orleans and southern-inspired tapas" that are both inventive and delicious. The menu boasts standout items like the "creamy crab dip, delicious biscuits, and spicy Viet/Cajun cauliflower," each crafted with meticulous attention to detail. Guests appreciate the opportunity to explore a range of flavors through sharing plates, making it perfect for a communal dining experience. With a vibrant atmosphere and "attentive and helpful service," Buttermilk & Bourbon is a must-visit for tapas enthusiasts.
A photo of Five Horses Tavern - South End restaurant
4.6
Exceptional(934)
Price: Moderate
• Comfort food • South End
Booked 10 times today
Five Horses Tavern - South End is a shining beacon of modern American cuisine in Boston's vibrant South End. With its mission to serve "modern American comfort food," this charming spot uses locally sourced ingredients to craft delicious dishes that cater to all dietary preferences, including vegetarian, vegan, and gluten-free options. Guests rave about the "amazing cocktails and delicious food," with the cornbread and Reuben sandwich frequently mentioned as must-tries. The tavern's extensive beer selection, featuring 40 drafts and 60 bottles, complements its cozy, welcoming atmosphere, making it a favorite for both locals and visitors. Whether for brunch, lunch, or dinner, Five Horses Tavern promises an authentic and memorable American dining experience.
A photo of 75 Chestnut restaurant
4.7
Exceptional(2412)
Price: Moderate
• Comfort food • Beacon Hill
Booked 43 times today
75 Chestnut, nestled in the charming streets of Beacon Hill, Boston, is a hidden gem for authentic Comfort Food cuisine. With over 20 years of serving the neighborhood, this cozy establishment delights diners with "fresh cooked-to-order foods" that have patrons returning time and again. The seafood stew and steak tips are particularly noteworthy, earning rave reviews for their delectable flavors. The restaurant's inviting ambiance is complemented by a "super friendly staff" that ensures a memorable dining experience. Whether indulging in their iconic gingerbread lunches or savoring the stuffed French toast during brunch, 75 Chestnut offers an unparalleled comfort food journey that's perfect for any occasion.
A photo of Bostonia Public House restaurant
4.6
Exceptional(3159)
Price: Expensive
• Comfort food • Financial District
Booked 90 times today
Bostonia Public House stands out as a beacon of exceptional American cuisine in the heart of Boston's Financial District. Known for its "remarkable" food and vibrant atmosphere, Bostonia offers dishes that capture the authentic essence of American flavors. From perfectly shucked oysters to the "hot lobster roll," each dish is a testament to the restaurant's commitment to quality and tradition. Guests rave about the "fantastic" brunch, featuring creative offerings and a renowned Bloody Mary bar. Whether for a lively dinner with live music or a cozy brunch, Bostonia Public House promises an unforgettable dining experience that celebrates American culinary heritage.
‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

See what locals rave about

From verified diners like you
From verified diners like you
  • constantineVIP
    Greater Boston •12 reviews
    4.0
    Dined 2 days ago
    Went there for the first time last night on Valentine’s Day. This is one of the new restaurants that has opened up in the alewife area now that there’s a lot of housing. They have nice friendly staff, but the service is a bit slow because they seemed understaffed with waiters. They have a bar shuffleboard table that’s kinda nice. Wasn’t crazy about the cocktail choices. Place seems to mostly cater to youger couples and our families with kids who live in the area. Food is average in my opinion, but not overpriced as the most expensive entrée is $31 and most are in the mid 20s. Also if you’re vegan or vegetarian, there aregood options here. The empanadas were very tasty. The dumplings are really thick on the dough and chewy  and then my wife, and I agreed that the vegetarian filling was a bit dry so you really needed to have with the spicy dipping sauce. The Bolognese was massively overcooked, and while the flavor of the sauce was good the pasta was an absolute mush. That dish was the biggest disappointment for me. The shaved brussels sprouts salad was quite tasty though with halloumi. I probably won’t go back as it’s not my scene and I prefer a higher level of dining. 
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    Mothership AlewifePrice: Moderate• American• Cambridge
    4.6
  • Walter RVIP
    Greater Boston •1 review
    5.0
    Dined 3 days ago
    The staff was exceptionally attentive and thoughtful!
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    Five Horses Tavern - Davis SquarePrice: Moderate• Contemporary American• Somerville
    4.5
  • Henry
    Greater Boston •2 reviews
    4.0
    Dined 5 days ago
    Phish and chips was fresh and fried well. I wish there was more seasoning in the fish but it was still satisfying. The Loaded Poutine Fries had flavorful short rib gravy. The Short Rib Sandwich was the winner! The meat was extremely flavorful and cooked well and the dipping gravy elevated it to another level! Unfortunately, the Mac and Cheese was a disappointment - the translucent cheese sauce lacked cheese flavor. This was quite regrettable considering the quality of our overall food experience. The environment was very comfortable and pleasant. It had creative pieces such as a chandelier made out of trumpets, lighting that looked like piano keys, and a hung guitar art piece made out of metal gears. The waiter was attentive, pleasant, and fulfilled our customized requests accurately, timely, and graciously. The live music was wonderful! The musician was great and the audio system was clear but not excessively loud. We felt comfortable to dance and really had a nice time!
    More info
    Goodnight Johnny’sPrice: Moderate• Grill• Burlington
    4.5
  • Gary
    Greater Boston •10 reviews
    4.0
    Dined 5 days ago
    Overall, pretty good. Only complaint was that I waited 15 mins to eat once my food came out because I was waiting on something to add to my meal and even asked three different servers to get it.
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    Tavern in the Square - BurlingtonPrice: Moderate• American• Burlington
    4.6
  • Tracy
    Greater Boston •7 reviews
    5.0
    Dined on Feb 7, 2025
    Such a great experience each time we have gone! Food/drink/service is on point! I love the monthly Tavern Treats as well!
    More info
    Town TavernPrice: Moderate• American• Arlington
    4.5
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