Best Historic Restaurants in Winchester

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchIndian

Regions

Boston

Neighborhoods

Back BayBeacon HillBrooklineCambridgeCharlestownDowntown Crossing

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

67 restaurants available nearby

How are Featured results ranked

A photo of Margeaux Supper Parlor restaurant

1. Margeaux Supper Parlor

4.5

Awesome(155)

$$$$Price: Expensive

• Contemporary American • Cambridge

Booked 25 times today

Margeaux Supper Parlor presents a novel way to experience dinner by telling stories through cuisine. Guests are encouraged to order a themed trio of dishes, larger than tapas and smaller than big plates, to better experience the menu and recreate the familial bonhomie we associate with supper at grandma’s (when you were urged to try a bite of everything!). Recommended wine pairings are served in collections to mirror the entree trios. Margeaux Supper Parlor serves New American cuisine, blending dishes inspired by the two most historic port cities in the country: New Orleans and Boston. Dinner plates include: Tomato & Bacon Jam Deviled Eggs (topped with a fried Maine oyster), Lamb Lollipops with cherry reduction, Pumpkin Ravioli, Beef Wellington, Shrimp & Boursin Grits, and Maple Bourbon Steak Tips.Brunch is also served in themed collections and includes items such as: Quiche Lorraine, Fried Chicken & Sweet Corn Waffle, Eggs Benedict, and a Black Forrest Waffle.

A photo of Premiere on Broadway restaurant

2. Premiere on Broadway

4.0

Excellent(294)

$$$$Price: Moderate

• Italian • Somerville

Booked 14 times today

In search of dinner and a show? The Premiere on Broadway is an exciting new restaurant and music venue located in the historic Magoun Square, Somerville. Featuring delicious cuisine, libations, beautiful artwork and fantastic live entertainment. The Premiere serves an array of Italian and American fare. At our 65-seat bar we offer delicious craft beers and an extensive classic Italian cocktail program; featuring negronis, Americanos, and Bellinis. We accept dinner reservations through OpenTable and over the phone. Walk-ins are welcome, but reservations are strongly recommended for full dinner service only. Our bar is first come first serve. Fri and Sat there is a $50 minimum per person for parties of 10 or more. After 8 p.m. I.D.s are checked at the door.For large party inquiries (private events, buyouts, holiday parties etc.) contact owner Koryn Zammuto at koryn.zammuto8@gmail.com.

A photo of The Vintage Tea & Cake Company - Lexington restaurant

3. The Vintage Tea & Cake Company - Lexington

4.8

Exceptional(124)

$$$$Price: Moderate

• Afternoon Tea • Lexington

Booked 6 times today

Our new Lexington Tea Room is a beautifully appointed and welcoming space located just off Massachusetts Ave on the corner of Muzzey and Raymond St. Enjoy teatime with friends in our bright, sun filled tea sanctuary. The larger of our two tearooms, on the weekends the Lexington location is a fun, buzzing space welcoming larger groups and parties. For a more intimate experience we recommend visiting during the week or trying our smaller Belmont location. Our tearoom is also ideal for private events 25+ guests. For advanced bookings please email us at vintageteaandcake@gmail.com.

A photo of Nirvana: The Taste of India restaurant

4. Nirvana: The Taste of India

4.5

Awesome(189)

$$$$Price: Moderate

• Indian • Cambridge

Booked 8 times today

Nirvana, an epicurean Indian restaurant in Cambridge presents traditional Indian cuisine with a contemporary flair. outdoor seating during the warmer months and a full-service bar with craft cocktails that flatter our flavor rich dishes. Our head chef Paramjit Singh hails from Punjab, India where the tandoor method of cooking originated. He brings over 20 years of experience to our kitchen and combines traditional cooking methods with novel ingredients to create innovative meals for our guests. As an 80-seat restaurant on historic Massachusetts Avenue, Nirvana endeavors to promote a transcendent experience through food, drink and great company.

5. Prima

4.7

Exceptional(952)

$$$$Price: Expensive

• Italian • Charlestown

Booked 69 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

6. Union Oyster House

4.5

Awesome(8773)

$$$$Price: Moderate

• Seafood • Faneuil Hall

Booked 129 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.

7. Ciao Roma

4.8

Exceptional(1110)

$$$$Price: Expensive

• Italian • North End

Booked 81 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.

8. Estella

4.3

Awesome(737)

$$$$Price: Expensive

• American • Downtown Crossing

Booked 84 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 Trattoria Il Panino restaurant

9. Trattoria Il Panino

4.5

Awesome(6593)

$$$$Price: Moderate

• Italian • North End

Booked 173 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.

10. Contessa - Boston

4.8

Exceptional(137)

$$$$Price: Expensive

• Italian • Back Bay

Booked 46 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.

See what locals rave about

From verified diners like you

M
Maya
Singapore •2 reviews
5.0
Dined 6 days ago
Our waitress was lovely - she brought out free champagne for us for our anniversary, the food was amazing - I highly recommend the vodka pasta and the yellow cake for dessert, and I loved the vibe of the place.
More info
PrimaPrice: Expensive• Italian• Charlestown
•
4.7
S
SoumyaVIP
Greater Boston •10 reviews
5.0
Dined on May 2, 2025
Food and service was excellent. The only drawback was that portions are kind of small for main entree for the price.
More info
Margeaux Supper ParlorPrice: Expensive• Contemporary American• Cambridge
•
4.5
E
Esther
San Francisco Bay Area •1 review
5.0
Dined on Apr 23, 2025
The service was perfect and the ambiance was lovely. The teas were very nice and were well timed with the food. The servers were very attentive. I would have liked a little more food like one more small sandwich but all and all it was a lovely experience.
More info
The Vintage Tea & Cake Company - LexingtonPrice: Moderate• Afternoon Tea• Lexington
•
4.8
E
ElenaVIP
Greater Boston •9 reviews
5.0
Dined on Apr 18, 2025
Great venue, very clean, with excellent food! Service was great too
More info
Premiere on BroadwayPrice: Moderate• Italian• Somerville
•
4
OT
OpenTable Diner
Philadelphia County •1 review
5.0
Dined on Mar 18, 2025
Amazing people amazing food!! Phenomenal dishes!!
More info
Nirvana: The Taste of IndiaPrice: Moderate• Indian• Cambridge
•
4.5

Explore OpenTable

Neighborhood
Historic

Winchester

West Cambridge
Reading
Charlestown
Marshfield
Weymouth
Rehoboth
Cambridge
Chestnut Hill
Framingham
Natick
Fenway–Kenmore
Sudbury
Newton
Wayland
Somerville
Logan Airport
Faneuil Hall
Lynn
Mattapan
Leather District