Of all the reasons to visit Boston, Massachusetts, experiencing the food that characterizes America’s walking city is one of the most intimate and enjoyable experiences. Dining throughout Boston’s neighbourhoods tells stories of history, diversity, and hospitality that are integral to Boston’s ever-evolving story.
This whistle-stop foodie guide to Boston will take you from a quintessential meal at America’s oldest-running restaurant to a bustling pastry staple in Chinatown. No matter what you’re looking for, you can count on finding a delightfully unassuming iteration in Boston. Keep on reading to find out where to eat for each meal of the day. Here’s our guide to the best Boston foodie spots to hit in 48 hours…
A Foodie Guide to Boston – Where to eat in Boston
Day 1
Kick off your Boston food experience with a morning at The Courtyard Tea Room tucked inside the Boston Public Library. This dining room is illuminated with large windows that provide views of the beautiful library courtyards. The arched ceilings are timeless and charming while the menu and tea selection is the perfect accompaniment. When enjoying tea you will indulge in a rotation of amuse bouches, an extensive selection of teas from around the world and a diverse selection of sandwiches, desserts and biscuits.
Following tea, explore the architecture at the library. For this, head from the courtyard to the grand staircase where you can be amazed at the stunning decor. This first stop is characteristic of Boston – a blend of cuisine, community, and history.
After experiencing original sandwiches paired with classic architecture at the public library, head to Boston’s historic Chinatown for an afternoon discovering Chinese culinary staples.
The blocks of Chinatown are narrow, but no space is wasted. Each street is filled with eateries, parks, salons, grocers, and herbalists and decorated with impactful street art – telling stories of Chinatown’s history and celebrating local icons. Boston’s Chinatown is the second largest Chinatown on the East Coast, second only to New York City’s. From the families relaxing at the park to teenagers grabbing boba tea after school, you will be sure to take in a vibrant subculture of Boston that also hosts distinct dining experiences.
Step into Jia Ho Supermarket (meaning “Family Harmony”) to roam the comprehensive mix of fresh produce, Chinese dishware, packaged snacks, and live seafood. Jia Ho shares an array of Chinese cooking staples to bring home.
Another must-stop in your Chinatown excursion is Ho Yuen Bakery. This bakery is prized for its traditional pastries such as almond cookies and mooncakes. Locals frequent Ho Yuen regularly, picking up their favourite pastries between meals. Chinatown has many storefronts where you can peel off for tea, Chinese barbecue, or even visit an expert herbalist at Nam Bac Hong. Take some time to wander around and take it all in.
Complete your tour at Hei La Moon for an exciting Dim Sum service. The many carts rolling the floor at Hei La Moon are filled with steaming bamboo baskets and piping teapots. Ask your server for some of their favorite dishes and prepare for a grand feast of the senses.
After taking the afternoon to enjoy the fascinating history of Chinatown, experience the food hall at High Street Place. Here, you can grab a beer, go for a round of cornhole, catch up on a sports game, and be immersed in a new Boston hub. High Street Place features a wide array of restaurants, cocktail bars, and live music. Here, Bostonians gather for happy hour after work, couples play cards for date night, and families enjoy the entertainment and vendors. This lively and eclectic spot will meet you with the best of whatever you’re looking for, even featuring a champagne vending machine – our personal favourite!
Complete your first-day dining in Boston at Stillwater. This spot shares their exciting take on American comfort food. Stillwater is located back at the edge of Chinatown. The menu is animated with unconventional cocktails and plates – central to the style of Stillwater’s founder, renowned Chef Sarah Wade.
The Caesar Brussels are a curious exploration of Brussel sprouts while the Cranberry Negroni is a smashing twist on the well-loved classic thanks to the cocktails’ irresistible addition of Cranberry infused Campari. Another cocktail favourite at this new-age American joint is the Stilly Espresso Martini, which is splashed with Nantucket Vanilla Vodka and Irish cream, resulting in an elevated familiar favourite. At Stillwater, southern comfort dishes and the Boston innovative spirit meet for a distinctly Boston experience.
Day Two
On day two, venture to an essential Boston institution, the Union Oyster House. You simply cannot leave Boston without enjoying a meal at the Union Oyster House – this experience certainly tops our list. Exciting, rich with stories, and perfectly hospitable, the Union Oyster House is a home base for Boston dining. The menu offers the quintessential Boston dining experience. Feast on the likes of Oysters, lobster, clam chowder, and cornbread, washed down with a classic, ice cold Sam Adams.
The Union Oyster House first began serving food in 1826, making this oyster house America’s longest-running restaurant. Plenty of political and celebrity regulars are welcomed into the doors and it’s a real must-see. The team here is proud to share the captivating history and one of our favourite stories is the surprising tale of Louis Philippe; Phillipe lived in exile on the second floor of the restaurant before his 18-year reign as king of the French. Akin to a museum gallery itself, take a tour of the intricate floors of the oyster house for charming mini-bars, decorated dining rooms, and for a seat at JFK’s favourite booth.
Later, make your way to the Fenway neighborhood for the Time Out Market. This food hall and patio features hand-picked selections of some of Boston’s best restaurants, chefs, and bars. If you’re feeling inspired to get cooking, be sure to check out the market’s demo kitchen for a rotating selection of cooking and cocktail crafting workshops.
Walk around the corner from the Time Out Market to reach DW French. Here you will enjoy a sophisticated French dinner with an extensive wine list, offering a wine selection spanning from Burgundy to the Willamette Valley. At DW French, the ambience will transport you to a proper French cafe. The black and white tile floors, red leather booths, and a bold statement bar (for those stopping by for the house’s adored take on the French Martini), make DW French a timeless and reliable Boston experience. You will be sure to find all of your favourite French dishes with expert wine pairings.
Complete your foodie weekend at the elegant, yet perfectly understated Oak Long Bar and Kitchen. This restaurant and bar at the Fairmont Copley Plaza offers refined, locally supplied dishes that are ideal for late-night eats and drinks. This Boston favourite is also commonly frequented as an elegant stop for locals before hitting the town. The Oak Long Bar and Kitchen is within earshot of our first destination, the Boston Public Library. Here you can enjoy dishes such as the stunning Seared Duck Breast, or the unsuspecting take on an East Coast classic, Cajun Shrimp and Grits. If you’re swinging by for a cocktail, enjoy one of the most divine dirty martinis in town or a delightful White Cosmo.
This whistle-stop food guide tells the authentic story of Boston – a city that celebrates its history while embracing innovation; a theme reflected throughout Boston’s menus, venues, and perfect hospitality. There is something very poignant about dining in between culinary influences of both the past and future. Traversing Boston’s neighbourhoods is a foodie haven offering distinct dining experiences, no matter what you’re looking for. What are your favourite places to eat in Boston? Let us know, we’d love to hear from you!
