The Back Bay is home to Boston’s tallest skyscrapers and its glitziest shopping, restaurants and hotels. But if you only stick to the famous commercial strips of Newbury Street and Boylston Street, you’d miss so much of the neighborhood.
“Back Bay is a great place to just roam,” says Courtney Flynn, manager of Trident Booksellers and Cafe. Flynn encourages people to zigzag their way through the neighborhoods’ parallel avenues to get a true sense of the place. Flynn’s parents opened Trident here on Newbury Street in 1984, so she and her family have witnessed both the things that have changed and the things that have stayed the same.
Unlike the retail on Newbury, Marlborough Street and its parallel neighbors Commonwealth Avenue and Beacon Street haven’t changed a bit. “My favorite place to walk down is Marlborough Street; I like to pretend that I live in one of the single-family brownstones,” says Flynn. She encourages visitors to meander down Commonwealth Avenue Mall, rubbing shoulders with the residents walking their dogs.
If you head in any direction, you’re likely to hit one of the Back Bay’s beautiful parks, from Copley Square (a grassy plaza shrouded by skyscrapers) to the Charles River Esplanade (Boston’s waterfront haven for runners, cyclists, sailors and other outdoorsy types). The access to outdoor spaces together with the beautiful historic buildings make Back Bay one of the most desirable places to live in the city – though it wasn’t always that way.
Up until the 1860s, the Back Bay was quite literally that – a bay of the Charles River, and not the gorgeous oceanfront kind. As it was a time before modern plumbing, the marshy bay was strewn with trash and sewage that would be carried down the river at high tide. In order to clean up the smelly area, expand the taxable land in the city and connect Beacon Hill with the Fens, work began to fill in the marshes with earth from surrounding neighborhoods and towns. This project resulted in the beautiful, flat waterfront region that today might be the most quintessential neighborhood in Boston. Wealthy citizens and developers purchased plots and built rows of Victorian and Edwardian brownstones, inviting the city’s most affluent residents to move in.
Flynn partially attributes Trident’s longevity to these local Back Bay residents, but they rely on the entire diverse range of people who filter through the neighborhood every day. “We kind of meet in the middle of the neighborhood. We’ve got regulars who live in the brownstones who come in every day, but we also have students [from Northeastern University, Boston University and Berklee College of Music], as well as tourists discovering the Trident while they’re here.”
Shopping is a big draw in this neighborhood, but so is the food. The Back Bay has a huge range of restaurants and bars covering cuisines from New England to Nordic. Saltie Girl serves creative New England seafood with a full range of preparations. Meanwhile, Parish Cafe offers a delicious and high-concept sandwich line-up, with each sandwich created by a different Boston chef, resulting in a menu that reads like a who’s who of the Boston culinary scene. Lolita is a high-end Mexican restaurant with a Gothic-esque, Day of the Dead interior and quirky touches like cotton candy accompanying your check. At the other end of the neighborhood, Chef Chang’s is a cheap and friendly hole in the wall serving authentic and spicy regional Chinese food. If you don’t mind the line (that inevitably runs out the door), Santouka Back Bay always does the trick, especially on a cold night.
Just a block over from Santouka, Trident is one of the last remaining independent shops on the western end of Newbury Street, which Flynn describes as the “hipper, cooler end, whereas the other side [closer to the park] is more high end.” For visitors, she recommends starting the day on the side closer to the Fens and making their way towards Boston Common on the opposite end of the neighborhood. Along the way, check out some of the other boutiques on the shopping strip. Local chain Newbury Comics sells many facets of pop culture, from vinyl records and streetwear apparel to movie memorabilia. Hip Japanese boutique Topdrawer sells design-forward accessories aimed at young travelers.
The route is dotted with charming bars and pubs. The quaint Irish pub The Bebop gained some serious cred when Bruce Springsteen dropped in to have a pint and watch some Berklee students perform one night in 2019. The tiny back patio at Casa Romero serves up killer margaritas, cold Pacificos, and home-made chips and salsa. If you’re feeling high brow, head to the OAK Long Bar + Kitchen inside the Fairmont Copley Plaza for a martini or two. Eataly, the sprawling Italian food superstore, is an experience in and of itself, and it’s hard to beat the patio seating on a sunny day when it rolls out a gelato cart and Aperol spritz bar.
Boylston Street is Newbury’s busy commercial neighbor, and generally speaking, Newbury is more pedestrian-friendly. But it would be a shame to miss the Boston Public Library, especially the courtyard that looks straight out of a European palace. It’s also worth checking out the Boston Marathon finish line and the famous running shop Marathon Sports, where outside you’ll see a memorial to those killed in the 2013 bombings.
You can also spend the afternoon at the Copley Square Farmers Market, where vendors sell fresh produce, candles, soaps and other take-home trinkets. This street also provides access to the Prudential Tower, with an observatory at the top that has sweeping views of the Back Bay and Boston beyond. Among the lines of brownstones, you might be able to spy college students between classes, tourists weaving through shops and Bostonians on their way to brunch.
“Back Bay is so many things, but really it’s so Boston,” reflects Flynn.