Best Historic Restaurants in Brookline

67 restaurants available nearby

1. Prima

4.8

Exceptional(760)

Price: Expensive

• Italian • Charlestown

Booked 90 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

4.3

Awesome(8673)

Price: Moderate

• Seafood • Faneuil Hall

Booked 138 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.

3. Grill 23 & Bar

4.8

Exceptional(8752)

Price: Very Expensive

• Steak • Back Bay

Booked 136 times today

Brandt family beef, New England seafood, seasonal produce, decadent desserts, a world-class wine list, outstanding service and warm hospitality. A truly American experience. Boston’s top steak and seafood grill for more than 30 years. Consistently named Boston's Best Steakhouse by The Improper Bostonian Magazine and Boston Magazine. A 2000+ bottle wine list that encompasses wines from around the world and is the only Boston recipient of Wine Spectator’s Grand Award.

4. Estella

4.1

Excellent(609)

Price: Expensive

• American • Beacon Hill

Booked 77 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.

5. Contessa - Boston

4.7

Exceptional(80)

Price: Expensive

• Italian • Back Bay

Booked 63 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.

6. Comfort Kitchen

4.7

Exceptional(618)

Price: Expensive

• Global, International • Dorchester

Booked 25 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.

7. Ciao Roma

4.8

Exceptional(1036)

Price: Expensive

• Italian • North End

Booked 69 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.

8. Mare

4.6

Exceptional(2908)

Price: Expensive

• Italian • North End

Booked 66 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.

9. Hojoko

4.6

Exceptional(979)

Price: Expensive

• Japanese • Fenway–Kenmore

Booked 16 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.

10. 75 Chestnut

4.7

Exceptional(2379)

Price: Moderate

• Contemporary American • Beacon Hill

Booked 51 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 .

See what locals rave about

From verified diners like you

A
Ani
Greater Boston •3 reviews
5.0
Dined 2 days ago
We loved our meal and service at Estella. Our server was attentive, answered our questions and checked in periodically to ask if we needed anything.
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EstellaPrice: Expensive• American• Beacon Hill
•
4.1
J
Justine
New York City •7 reviews
5.0
Dined 5 days ago
Impressed by this establishment. We wanted fine dining in Boston and we got it. I had the halibut and it was amazing. My husband had a steak, also amazing. My daughter and son were able to slit the heritage chicken and it was plenty. Sides are shareable. My husband’s brown sugar old fashioned was Pinterest worthy. I had an espresso martini x 2 with amazing taste and a frosted glass which kept it cold for the little time that it lasted. Ambiance is elegant. They were well decorated for Christmas. Coat check was a nice surprise. The service was impeccable. We will return.
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Grill 23 & BarPrice: Very Expensive• Steak• Back Bay
•
4.8
A
Anastashia
Greater Boston •3 reviews
5.0
Dined 5 days ago
A magical experience! The food was incredible - we went for gluten free night because my husband has celiac and they did not disappoint.
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PrimaPrice: Expensive• Italian• Charlestown
•
4.8
D
Daniel
Greater Boston •2 reviews
5.0
Dined 5 days ago
Only ding on the service was that following shift change, we had trouble getting our check. Only ding on the "chowda" was it could have been a little warmer. Otherwise, this remains a great spot for a good meal!
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Union Oyster HousePrice: Moderate• Seafood• Faneuil Hall
•
4.3
D
DanteVIP
San Francisco Bay Area •10 reviews
5.0
Dined on Dec 19, 2024
incredible experience! attentive service & excellent food!
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Contessa - BostonPrice: Expensive• Italian• Back Bay
•
4.7

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Brookline

Best Historic Restaurants in Brookline

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67 restaurants available nearby

1. Prima

2. Union Oyster House

3. Grill 23 & Bar

4. Estella

5. Contessa - Boston

6. Comfort Kitchen

7. Ciao Roma

8. Mare

9. Hojoko

10. 75 Chestnut

See what locals rave about

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