The Most Fun Restaurants in Boston

Located in the heart of New England, Boston stands out as a historic American city, rich with culture and entertainment. A visit here offers all the benefits of a big metropolis without the intensity and fast pace of larger cities. Visitors can easily get around on the T or by bike to observe the many wide-open green spaces, trendy neighborhoods, and world-class museums. Plus, Boston has a culinary scene that foodies travel from near and far to enjoy. But where are the smartest, savviest diners eating out when looking for a good time? Welcome to the Tastemaker Lists. We’ve pulled data from thousands of restaurants to find the top spots among OpenTable's most expert, seasoned diners. If you’re looking for a dining spot where you can enjoy great food and an entertaining environment, check out our Tastemaker 20 List of the most fun restaurants in Boston.

The OpenTable Team

13 Restaurants

Updated August 16, 2021

Restaurants:	Brassica Kitchen, Season To Taste, Fat Hen Broadway East…
Price Range:	$$$ - $$$
Cuisines:	French / American, American, Italian…
Neighborhoods:	Jamaica Plain, Cambridge, Somerville…

Brassica Kitchen

$$$$

French / American

Jamaica Plain

4.9

1373 reviews

Brassica Kitchen and Cafe is the brainchild of the Whisk pop-up team. It's a bustling coffeehouse by day and intimate bistro by night. The kitchen churns out amazing dinners at night with a focus on fermentation-forward food and drink with locally sourced and seasonal ingredients. They offer a shared tasting menu of French American plates as well as a la carte selections. Come in with a group to enjoy their creative French-American cooking and indulge in a drink from the full cocktail, beer and wine menu.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Season To Taste

$$$$

American

Cambridge

4.8

1307 reviews

Season To Taste is a funky twenty-seat restaurant featuring an open kitchen and warm, intimate environment. Wedged into an unassuming block in a quiet corner of Cambridge, it features local, seasonally driven dishes prepared by Chef Robert Harris & team. The menu is a mix of light snacks and a la carte dishes paired with choice wines and craft beers. Chefs go out of the way to make sure diners have a good time here, often visiting each table personally throughout the course of the night.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Fat Hen Broadway East

$$$$

Italian

Somerville

4.6

354 reviews

The Fat Hen, located near Tufts University and Assembly Row in the Somerville neighborhood of Boston, is a casual elegant Italian restaurant. Diners love the sophisticated atmosphere and it’s perfect if you’re looking for a fine dining experience that also encourages you to have fun! The menu features traditional Italian dishes like bowls of fresh pasta, braised meats and locally grown or foraged produce as well as a killer list of Italian wines. Highlights include the spaghetti with Jonah crab, rigatoni wtih rabbit sausage and antipasti like stuffed morels, fluke crudo and tramezzini.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Forage

$$$$

Contemporary American

Cambridge

4.7

1272 reviews

If you’re looking for a super fun restaurant in Cambridge, head to Forage on Craigie Circle. It’s a farm-to-table neighborhood bistro right off Harvard Square that serves up casual, contemporary American food. They partner with local farmers, fishermen and foragers to invent sensational dishes and classically crafted cocktails. Forage is the concept of Owner Stan Hilbert, chef Eric Cooper and bar manager Joe Choiniere, the three of whom used to run Ten Tables in Jamaica Plain. Come in fora comfortable, down-to-earth environment and dishes like Chickpea Socca, Rosemary Pappardelle Pasta and Fried Bluefish.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Experiences available

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Dona Habana

$$$$

Cuban

South End

4.6

1219 reviews

Dona Habana is definitely one of the most fun restaurants in Boston - ask any local! The space feels like a tropical paradise and you’ll feel like you’re in Old Havana, Cuba the second you step inside. There are beautiful murals on the wall, low lighting and a cocktail list that includes 53 amazing mojitos and other tropical delights. Indulge in the fantastic Cuban cuisine and sample their unique fusion of native Taino, Spanish, African and Caribbean food. They have live music in the lounge on weekends, a great time to stop by for dinner and enjoy the festive atmosphere!

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Experiences available

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Takeout available

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Gustazo Cuban Kitchen & Bar - Cambridge

$$$$

Cuban

Cambridge

4.7

761 reviews

Gustazo is another lively and fun restaurant in Cambridge right on Massachusetts Ave. The word Gustavo means great pleasure and that is what you’re bound to find here. They aim to bring authentic Cuban flavors to the culinary scene in Boston. Step inside and find festive and colorful decor in the spirit of Havana - the interior has Spanish colonial architecture and vibrant Cuban art on the walls. The menu features a huge range of tapas dishes, like Chicharrones, Ropa Vieja Tacos, and Empanadas, as well as salads, sides and large plates. House favorites include large plates like the Puerco Asado, Salmon al Mango and Bistec Encebollado.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

La Fabrica Central

$$$$

Latin / Spanish

Cambridge

4.7

816 reviews

Located right in the heart of Cambridge, La Fabrica Central is a fabulously fun Caribbean restaurant from celebrity chef Giovanna Huyke. She is a cookbook author and popular TV personality in Puerto Rico and her menu of small plates, salads, soupy rice and more is a hit with locals and tourists alike. The Central Square hybrid offers Caribbean food in the front dining room, including Cuban, Jamaican and Puerto Rican, and a stage for live music and other events in the back. Try some of the house favorites, like the Chicharron de Pollo, Bolitas de Yuca con Queso and Asopao de Mariscos.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Menton

$$$$

French

Fort Point Channel

4.5

2566 reviews

Menton, located in Fort Point Channel, is the perfect stop for those looking for a fun night out in the neighborhood. The restaurant is Chef Barbara Lynch’s modern interpretation of fine dining and she focuses on beautifully executed cuisine, a stellar wine list and great service, all in a gorgeous upscale setting. The interior features a six-seat bar and tables along a banquette and diners get personal attention throughout the meal. Order a la carte or splurge on the Chef’s Whim menu, which features options like Fettuccine with braised lamb, Beef Cheeks and Turbot.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Dali

$$$$

Spanish

Cambridge

4.8

1264 reviews

For traditional Spanish cuisine in a fun setting that will spice up your night, head to Dali on Washington Street in Cambridge. The interior is bright and colorful with artwork on the walls, a tin ceiling and warm vibes. Owners Mario Leon and Tamara Bourso dish out fanciful plates with all the flavors of Spain. Guests can order a variety of small plates in order to sample all sorts of proteins, vegetables and interesting concoctions. House specialties include beef short ribs in a wine sauce, grilled lamb chops, shrimp scallop ravioli and more. If you’re feeling adventurous, try one of the plates of whole baked fish!

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Moonshine 152

$$$$

American

South Boston

4.9

1407 reviews

Moonshine, located on Dorchester Ave in Boston, is a modern neighborhood restaurant that serves up creative American cuisine. It’s a popular late night spot in South Boston with a weekend brunch that also attracts a big crowd. Come in for the rotating Jell-O shots! They have plenty of awesome drink specials all night that keep the crowd full and lively until the wee hours. Order some of the small plates to share with a group of friends - house favorites include the Street Corn Salad, Jalapeno Crab Rangoons, and Throwback Korean BBQ Tacos.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Shaking Crab - Boston Common

$$$$

Cajun

Downtown Crossing

3.9

124 reviews

Shaking Crab, located in Downtown Crossing, is one of the most fun restaurants in Boston for those who love to get messy! Their vision for messy eating started with the core belief that food can provide sustenance as well as an experience to share with your friends! That’s why they serve their Cajun-style crab here with a plastic baggy in which you can shake it up with your choice of sauces and spiciness. Then choose from apps, sides and other options like mac and cheese or fried pickles. Don’t worry, meals come with a bib and gloves so only your face will really get messy!

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Estragon

$$$$

Spanish

South End

4.6

1262 reviews

Estragon Tapas Bar, established in 2008, offers a slice of Spain in the South End. Owned and operated by Julio de Haro and Laura Egger, the cuisine reflects their love of simplicity and tradition. The menu features many family recipes including extensive tapas options and a unique cocktail list, over 20 local and craft beers and a lengthy list of Spanish wines. An evening here is all about having a good time and the decor is modern, festive and fun. Some of the most popular tapas options include Queso de Cabra, Croquetas de Bacalo, and a variety of Enlatados.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

FiRE+iCE Boston

$$$$

American

Back Bay

4.1

2945 reviews

Fire and Ice, located on Berkeley Street in the Back Bay, is a casual American place that is all about celebrating! They feature an interactive, all-you-can-eat experience in which every guest can create their own masterpiece on the plate. You get to choose from ingredients, sauces, toppings and more and cook it up over the open flame grill. It’s the perfect spot for a family outing, group get-together or a fun date night!

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Experiences available

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Takeout available

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