Best Historic Restaurants in Brookline

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchIndian

Regions

Boston

Neighborhoods

Back BayBeacon HillBrooklineCambridgeCharlestownChinatown

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Wheelchair access

70 restaurants available nearby

How are Featured results ranked

A photo of Union Oyster House restaurant

1. Union Oyster House

4.4

Awesome(8889)

$$$$Price: Moderate

• Seafood • Faneuil Hall

Booked 155 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.

2. Prima

4.7

Exceptional(1017)

$$$$Price: Expensive

• Italian • Charlestown

Booked 53 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.

3. Ciao Roma

4.7

Exceptional(1144)

$$$$Price: Expensive

• Italian • North End

Booked 107 times today

Located in Boston's North End, Ciao Roma offers a unique Southern Italian dining experience with a modern touch. Enjoy authentic flavors with dishes made using fresh, seasonal ingredients while also serving classics such as, Pappardelle Bolognese and Chicken Parmigiana. Pair your meal with our curated wine list and refreshing cocktails. And don't forget to try our award winning espresso martini! Join us for our Italian-inspired weekend brunch or dine al fresco on our patio during the summer. Perfect for date night, birthdays, anniversaries, and special occasions, our restaurant provides an elegant setting with views of historic North Square.

4. Estella

4.2

Awesome(783)

$$$$Price: Expensive

• American • Downtown Crossing

Booked 52 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

4.8

Exceptional(167)

$$$$Price: Expensive

• Italian • Back Bay

Booked 61 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. 1928 Beacon Hill

4.7

Exceptional(567)

$$$$Price: Very Expensive

• Contemporary French / American • Beacon Hill

Booked 41 times today

Welcome to 1928 Beacon Hill — where seasonal, eclectic American cuisine meets worldly flavors in a sophisticated, speakeasy-inspired setting. Under the culinary direction of Culinary Director Chris Maxson, our kitchen crafts innovative dishes designed to captivate the senses and elevate your dining experience.Nestled in the heart of historic Beacon Hill, just steps from the iconic Boston Common and the scenic Charles River Esplanade, we offer a destination dining experience for both locals and visitors. Our intimate dining spaces, featuring vintage-inspired décor, create a warm and inviting atmosphere ideal for romantic evenings, gatherings with friends, or special celebrations.Whether you're sipping on our prohibition-era cocktails or savoring world-class wines, 1928 Beacon Hill promises a dining experience that is both memorable and uniquely Boston.

7. Hojoko

4.4

Awesome(1024)

$$$$Price: Expensive

• Japanese • Fenway–Kenmore

Booked 29 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.

8. Wusong Road

4.8

Exceptional(728)

$$$$Price: Expensive

• Polynesian • Cambridge

Booked 56 times today

Wusong Tiki Bar is Cambridge's local tropical Bar serving Chinese American bar bites and tropical Tiki inspired drinks by Chef Jason Doo. Famous for our hand-made baos, crab Rangoons and the best Mai Tai in Boston. Please note if there are no tables available our ground floor bar and 2nd floor bar are available for guests without bookings--subject to availability and during peak hours there may be a queue.All reservations are for a 90-minute experience, and we kindly ask that you respect the guests who follow.Wusong Road is a minority and LGBTQ owned business.

9. Riccardo's

4.5

Awesome(2850)

$$$$Price: Expensive

• Italian • North End

Booked 49 times today

Riccardo's Ristorante is a cozy family run business in the historic North End of Boston, since 1994.Follow the Freedom Trail from Faneuil Hall and Rose Kennedy Greenway, across from Paul Revere's house.Try our infamous ricotta stuffed meatballs-shhh, they are not on the menu but available anytime. In addition to the traditional Italian favorite, Chicken Parmigiano, we are known for our delicious Eggplant Rollatini and Seafood Fra Diavlo. We offer Gluten Free pasta to ensure every guest is included-when you walk in, you are part of the family.

A photo of Chart House Restaurant - Boston restaurant

10. Chart House Restaurant - Boston

4.4

Awesome(5556)

$$$$Price: Moderate

• Seafood • Financial District

Booked 74 times today

Chart House is a fine dining restaurant serving seafood & steak and famous for their spectacular views. For more than 50 years, Chart House has redefined the ideal dining experience. With 26 waterfront and showcase locations ranging from the historic to the unforgettable, Chart House restaurants specialize in dazzling views, unique cuisine and exceptional service. From fresh fish specialties and seasonal seafood to slow-roasted prime rib and craft cocktails, the renowned chefs of Chart House have tailored a menu that adds a unique touch to local flavors. And the Chart House happy hour is a guest favorite, where guest favor our signature cocktails and delicious bites you are sure to enjoy. Our original Hot Chocolate Lava Cake is the perfect end to a memorable dining experience at Chart House. Chart House offers the ideal setting for your next event. We would be happy to assist you with all the details of your special occasion.

See what locals rave about

From verified diners like you

R
Robert
Orlando / Central Florida East •1 review
5.0
Dined 2 days ago
Great food and drinks. One of the best spots in town.
More info
EstellaPrice: Expensive• American• Downtown Crossing
•
4.2
M
Matt
Vancouver / British Columbia •20 reviews
5.0
Dined 4 days ago
Excellent food and service! My mother-in-law (Nona) would approve!
More info
Ciao RomaPrice: Expensive• Italian• North End
•
4.7
J
JillVIP
Greater Boston •39 reviews
5.0
Dined 5 days ago
Great ambiance - decor, greeted warmly and in a welcoming manner, even though we were delayed in arrival due to an unforeseen issue - nice table by the window, lively place w/terrific service and Delicious entrees. We enjoyed Chicken Piccata and Chicken Milanese w/Pasta, both cooked to perfection. We especially enjoyed one of the appetizers - Bread Plate presented well w/tasty fresh ricotta, potato focaccia, and sesame semolina baguette. Crisp, chilled Pinot Grigio was lovely as was the selection of Pinot Noir. Fabulous Dinner - very enjoyable! Will look forward to future visits and trying the charming outdoor seating next time!
More info
PrimaPrice: Expensive• Italian• Charlestown
•
4.7
B
berenice
Las Vegas •1 review
5.0
Dined 6 days ago
Our waitress was from Romania and she was very good and delightful
More info
Union Oyster HousePrice: Moderate• Seafood• Faneuil Hall
•
4.4
V
VivienVIP
Washington, D.C. Area •7 reviews
5.0
Dined 7 days ago
great food, great place and great service. would recommend
More info
Contessa - BostonPrice: Expensive• Italian• Back Bay
•
4.8

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