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Best Historic Restaurants in Brookline

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67 restaurants available nearby

A photo of Prima restaurant
1. Prima
4.8
Exceptional(783)
Price: Expensive
• Italian • Charlestown
Booked 82 times today
Located on the edge of City Square Park in Charlestown, Prima is an energetic Italian celebration of reimagined classics. Our beautifully restored grand bar and dining room – which overlooks the park as well as the city skyline – strives to honor our building’s past and its prestigious placement at the gate of this historic Boston neighborhood.
A photo of Union Oyster House restaurant
2. Union Oyster House
4.4
Awesome(8691)
Price: Moderate
• Seafood • Faneuil Hall
Booked 43 times today
The Union Oyster House, located on the Freedom Trail, near Faneuil Hall, enjoys the unique distinction of being America's oldest restaurant. This Boston fixture, housed in a building dating back to Pre-Revolutionary days, started serving food in 1826 and has continued ever since with the stalls and oyster bar, where Daniel Webster was a constant customer, in their original positions.
A photo of Trattoria Il Panino restaurant
3. Trattoria Il Panino
4.5
Awesome(6442)
Price: Moderate
• Italian • North End
Booked 163 times today
Trattoria Il Panino is the kind of place that one would expect to find along the Amalfi Coast. It is a warm, friendly, unpretentious and a food-focused environment. From the casual and positive energy of the atmosphere and waitstaff, to the serious and professional energy of the kitchen, the frontand back of the house form a desirable marriage. The entrance on 260 Hanover street has a full liquor license.
A photo of Estella restaurant
4. Estella
4.1
Excellent(617)
Price: Expensive
• American • Beacon Hill
Booked 30 times today
Estella Restaurant, a culinary gem in downtown Boston, invites you to an exceptional dining experience that fuses flavors from diverse cultures. Founded by George Brandão in tribute to his extraordinary mother, Estella—a beacon of love and dedication—the restaurant embodies unity and diversity at its core. Our signature dish, the Famous Worrell Oxtail Rasta Pasta, is a harmonious blend of tender oxtail and vibrant Caribbean spices, a must-try for food enthusiasts seeking unique flavors. Estella has been featured in prestigious publications such as Eater Boston's Best Restaurants in Downtown Crossing and Best Cocktail Bars in Boston. Located steps away from iconic landmarks like the Boston Common and the historic Freedom Trail, Estella is the perfect destination for locals and visitors seeking an extraordinary dining experience. Join us, where every dish tells a story and every moment celebrates culture, unity, and culinary artistry.
A photo of Contessa - Boston restaurant
5. Contessa - Boston
4.7
Exceptional(93)
Price: Expensive
• Italian • Back Bay
Booked 48 times today
Perched atop The Newbury Hotel like a crown jewel, Contessa is a grand destination. Guests are welcomed from morning till night to a sunlit, rooftop restaurant with Art Deco references and mid-century modern detailing, offering sweeping views of Back Bay and the Boston Public Garden. The menu offers a wide variety of delicious options, from feasts of antipasti, carpaccios and pizzas, to pastas and large steaks. A vast wine list, classic cocktails and a selection of dolci punctuate a beautiful meal.
A photo of Comfort Kitchen restaurant
6. Comfort Kitchen
4.7
Exceptional(630)
Price: Expensive
• Global, International • Dorchester
Booked 37 times today
Nested in Uphams Corner, Dorchester, we're a lively and intimate 30-seat restaurant serving brunch on the weekend and dinner at night with a full bar and outdoor patio. Our food is a celebration of the ingredients and flavors of the African diaspora connected from Asia to the Americas — global comfort food. We are proudly Black-owned, immigrant-owned, and women-owned. We believe that food is a vital aspect of community building and we envision a place that is actively engaged in highlighting the culture, art, and history of our community.- Patio dining: patio reservations are weather-dependent and may be canceled due to inclement weather. Our patios are partially covered protecting from light to moderate rain and light wind. - Timing: dinner's last seating is at 8:45pm and brunch's last seating is at 1:30pm. Your table is reserved for 90 mins for parties of 1-5 guests and 2 hrs for parties of 6+ guests.
A photo of Ciao Roma restaurant
7. Ciao Roma
4.8
Exceptional(1044)
Price: Expensive
• Italian • North End
Booked 33 times today
Italian restaurant using the freshest ingredients and house-made pasta. Focusing on Southern Italian cuisine, we serve a full bar and curated wine list. Located on the historic Freedom Trail overlooking North Square.
A photo of 75 Chestnut restaurant
8. 75 Chestnut
4.7
Exceptional(2389)
Price: Moderate
• Contemporary American • Beacon Hill
Booked 30 times today
75 Chestnut - Nestled amidst the brownstones on the charming streets of Beacon Hill. Features regional American food. Serving our neighborhood for the last 20+ years we are delighted to welcome you to our establishment. We are proud that we can serve our fresh cooked to order foods, specialty crafted drinks and cocktails. Our super friendly staff will make you want to come back again and again. we are the essential Beacon Hill restaurant a must see for residents and visitors alike. Our seafood stew and steak tips have our guests wanting to come back. We serve dinner seven nights a week and we serve brunch and lunch on Saturdays and Sundays. the stuffed French toast is something you don't want to miss. during the seasons we always feature food and drink specials and special events. some examples are sweet tooth Tuesdays, wine Wednesdays, green Thursdays, Sunday supper. our Ginger bread lunches are iconic so book soon. we will be happy to serve you .
A photo of Mare restaurant
9. Mare
4.6
Exceptional(2924)
Price: Expensive
• Italian • North End
Booked 39 times today
Mare, Italian for ‘sea’ , has quickly become this city’s most acclaimed seafood restaurant with accolades such as “One of the Top 80 Tables in the World” by Conde Nast Traveler and “Go to List” Food & Wine. Please visit our new location at 3 Mechanic St.
A photo of Hojoko restaurant
10. Hojoko
4.6
Exceptional(981)
Price: Expensive
• Japanese • Fenway–Kenmore
Booked 12 times today
Hojoko is a rock n roll izakaya honoring the pulse of Japanese nightlife by serving sushi, robata grilled yakitori and street food small plates paired with craft cocktails, premium sake, wine, and beer. Located directly behind historic Fenway Stadium and walking distance from The MGM Fenway and The House of Blues, Hojoko is the perfect stop before any event. Dishes like our Wagyu Cheeseburger, Wasabi Roulette, and our 48-hour Ramens keep locals and travelers coming back. Several unique spaces in the restaurant make it the perfect place for a business dinner, birthday celebration, or event gathering space.

See what locals rave about

From verified diners like you
From verified diners like you
  • William
    Central and Western MA •3 reviews
    5.0
    Dined 1 day ago
    This establishment did an outstanding job at fulfilling our requests and seated us at the table I had specifically asked for. The food was delicious and the prices are fairly reasonable, but the service was above and beyond tonight. Thank you Union Oyster House servers!!!
    More info
    Union Oyster HousePrice: Moderate• Seafood• Faneuil Hall
    •
    4.4
  • NataliaVIP
    Greater Boston •3 reviews
    5.0
    Dined 4 days ago
    Hostesses were not pleasant and not accommodating at all when we got there early and did not show any effort in trying to find us a table. Not exactly what I call customer service. With that being said, we have been there 3 times within the last 2 months because of the lively atmosphere, great Italian food and amazing cocktails and bar staff.
    More info
    PrimaPrice: Expensive• Italian• Charlestown
    •
    4.8
  • Tim
    Greater Boston •1 review
    5.0
    Dined 5 days ago
    Came here for a post-egagement dinner, staff was very welcoming and congratulatory and brought complimentary prosecco. They let us stay for a while drinking and celebrating, wonderful atmosphere!
    More info
    Trattoria Il PaninoPrice: Moderate• Italian• North End
    •
    4.5
  • MaureenVIP
    Greater Boston •47 reviews
    5.0
    Dined on 1 Jan 2025
    We had an amazing meal to bring in the New Year at Contessa’s! The view was delightful with Christmas lights, the State House, Church steeple and the high rises along with The Public Garden. Pedro, our server, and Sarai were so attentive! The focaccia bread and smoked olives were a pleasant start. The entrées were scrumptious! Pasta was perfect. Dessert was delicious! Thank you, Pedro and Sarai!
    More info
    Contessa - BostonPrice: Expensive• Italian• Back Bay
    •
    4.7
  • sean
    Southwest Florida •10 reviews
    5.0
    Dined on 30 Dec 2024
    This was a trip with my girlfriend and I to Boston for the New Years weekend. We had breakfast, lunch and dinner at various places. This place had an amazing Blue Cheese burger that was so delicious! They made some amazing smoked old-fashioned drinks as well! Definitely would go back when up in Boston!
    More info
    EstellaPrice: Expensive• American• Beacon Hill
    •
    4.1

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