All Articles 4 Boston neighborhoods you don't want to miss

4 Boston neighborhoods you don't want to miss

A local’s guide to strolling and staying in the city.

Joanna Rakoff
By Joanna Rakoff8 Apr 2024 8 minutes read
Reflection of Boston skyline in the Boston waterfront.
Boston Skyline
Image: gettyimages/DenisTangneyJr

We all know plenty of people who come to Boston for the Colonial history. But there’s much more to New England’s capital than the Freedom Trail and Fanieul Hall (though those are pretty amazing).

These four neighborhoods drip with classic Boston charm—red brick, cobblestones, and ivy everywhere. They offer easy access to all the must-see sites for a first-time visitor, but also have magical spots loved by locals like me. Boston is a city of nooks and crannies, and many of its best cafes, venues, and shops can be found in hidden-away alleys or narrow side streets. So prepare yourself to veer off the main byways. I promise it will be worth it.

All four of these neighborhoods are perfect jumping-off points for exploring the city on foot, with great hotels and easy train and bus access.

Harvard Square

Aerial view of Harvard Square with bustling traffic.
Bustling Harvard Square near Cambridge
Image: Getty images/JohnColetti

Harvard Square, of course, takes its name from that famous American university with the grand buildings that sprawl in and around the square. Even if you and yours have no interest in applying, start the morning with a history-laden campus tour led by a current student to get a feel for the area. (Tip: Register early as tours book up months in advance.)

But first, coffee. Before you meet your guide, head to my favorite cafe, Faro, on tiny Arrow Street. Everything is tasty, but the ambiance is the real draw: Faro doesn’t allow electronic devices, so the tables are filled with people quietly reading and writing or talking to each other! (Make sure to pick up a few of their gluten-free almond cookies for later.) Post-tour, stop at Tatte—a popular local chain of French-Israeli bistros—for a salad niçoise or shakshuka. Grab a seat on the sunny second floor, where you’ll be surrounded by students intensely studying and sipping Tatte’s trademark sesame latte.

While visitors crowd Boston’s more famed museums—the MFA and the Gardner—head to the city’s best-kept secret: The Harvard Art Museums, recently renovated by Renzo Piano. These spectacular, sun-filled galleries have breathtaking Sargents and Whistlers, an enormous collection of ancient Asian art, and so much more, including a lovely café. (I’m a fan of their brownies.) You’ll also find the incredible Harvard Museum of Natural History a few blocks away.

But there’s another reason locals love Harvard Square: The adorable shops. One of my favorites is Harvard Bookstore, which has a vast selection of new and used tomes. The Attic a perfectly curated and refreshingly inexpensive vintage shop (don’t miss the $5 and $10 bins). Mint Julep is the kind of women’s clothing shop I wish every city had. It’s known for stocking indie designers and styles for every age, sensibility, and shape. L.A. Burdick, a beloved Viennese-style confectionary and patisserie, is known for its hot chocolate and candy mice.

For dinner, my family’s favorites are Felipe’s Taqueria, the closest you’ll get to LA-style tacos in New England, Madras Dosa Company, and kitschy tiki bar Wu Song Road. For a more leisurely meal, try Waypoint for oysters and seared fish, The Painted Burro for inventive Mexican fare, or the Brooklyn-ish bistro Alden & Harlow.

Where to stay: At the heart of the square, the cozy, library-like Charles Hotel offers gorgeous views of the Charles River. April through November, you’ll spy crew teams rowing by in skiffs. They also have a serene spa, and two fantastic restaurants, the beloved Henrietta’s Table and the newer trattoria Bar Enza. A less pricey but equally charming option is Hotel Veritas, a glamorously outfitted joint in a quirky Victorian building with warm, kind staff and peaceful, spacious rooms.

More to explore

Beacon Hill

Cobblestone pathway along the historic brownstone townhouses of Beacon Hill.
Historic brownstone townhouses of Beacon Hill
Image: Getty images/benedek

When you close your eyes and imagine Boston, you’re probably picturing Beacon Hill. With its cobblestone streets, brick sidewalks, stately row houses, and gas lamps, a walk along the main drag, Charles Street, can feel like time-traveling back a century. Charles Street has enough delightful shops to while away half the day.

Filled with luxuriously upholstered sofas and ornate woodwork, the sun-drenched, multistory Beacon Hill Books and Cafe, in an Edwardian townhouse, feels like a Gilded Age private library. Covet, Boston’s best consignment shop, has incredible deals on everything from Chanel to Zara. Teens love Vico Style, an 80s-focused vintage shop, and Petunia, which looks like Cher’s closet in Clueless. Ouimillie and French + Italian offer cool-girl fashion for the slightly older set. The fun is really in the wandering, when it comes to Beacon Hill. I highly recommend winding your way along tiny Acorn Street or many of the other side streets, where you’ll be transported to colonial times, no tour guide necessary, particularly if you’re visiting at dusk, when the gas lamps flicker on. (Tip: October is a dream time to see Beacon Hill, as the residents go all-out on Halloween decorations, turning courtyards into haunted houses.)

When you’re tired of wandering, grab a pizza at Figs, a salad at Cobblestones, or a grilled cheese at the Paramount, all Charles Street institutions—though I’ll confess that I tend to eat at the nearby branch of my beloved Tatte. Then veer into the Hill’s North Slope, once home to immigrant communities, like the Eastern European Jews who built the Vilna Shul, known for its lovely stained glass windows. It’s now a small, but fascinating museum, which you can visit en route to the African Meeting House, the oldest black church in the United States and a crucial stop on the Underground Railroad. It is also now a museum.

Beacon Hill also has a number of historic homes preserved in all their Gilded Age glory—Nichols House, William Hickling Prescott House, and Gibson House, to name just a few.

For a very different slice of history, visit Cheers, the actual bar that inspired the iconic television show, its logo unchanged since the 1980s.

Where to stay: For a hotel that’s seriously an experience, try The Liberty, in the former Charles Street Jail. Gorgeous and elegant, but with a fun, freewheeling vibe and a number of popular restaurants, like Clink, and bars. For a more quiet stay, book a room at the lovely Whitney or the XV Beacon, which has a plethora of spacious suites suitable for families.

Explore Boston’s Vietnamese community

The Seaport

Docked boats in slips in the Seaport district of Boston.
Boston Seaport district
Image: Getty images/denistangneyjr

Once an abandoned industrial area, in recent years the Seaport has become the city’s most fun, vibrant neighborhood, with spectacular new outposts of beloved local shops and restaurants lining the ancient cobblestone pathways along the water.

The airy new branch of Porter Square Books houses a great coffee shop and a proper stage for their marquee-name author events. In the summer, the lawns along the Fan Pier are filled with sun-starved Bostonians enjoying the warm weather and maybe taking in a free outdoor concert. In winter, crowds browse the large outdoor holiday market, try their hand at curling, or have drinks in a plexiglass igloo.

For me, a dream day at the Seaport would start with a cappuccino at Cocorico, the French-inspired café in the Omni Boston Hotel, or Flour, celebrity chef Joanne Chang’s wildly popular local chain of bakery/cafes, and a visit to the Institute of Contemporary Art, which has a vibrant permanent collection, as well as rotating exhibits from the world’s most exciting contemporary artists. For kids, the ICA’s wonder lies in the building itself. Its walls of windows make you feel as if you’re floating above the water. In summer, the museum runs boats across the harbor to their new Watershed gallery, housed in an abandoned copper pipe factory. (Reserve your spot in advance; they fill up quickly.) Lunch at the ICA’s courtyard bistro transcends the usual museum cafe fare and has options for all ages.

If my children were with me, they’d be clamoring to head to the New England Aquarium (my kids’ favorite: the electric blue lobster!), the vast and almost unbelievably fun Boston Children’s Museum, with its three-story climbing structure, or the Boston Tea Party Ships and Museum, housed in a colonial era ship and featuring actors in period costume who explain the American revolution in full-on dialect. All three are within easy reach of the Seaport and truly delightful, not just for kids.

For dinner, I’d land at my absolute favorite restaurant in Boston, Woods Hill Pier 4, which sits on a gorgeous corner overlooking the water; we celebrate birthdays and graduations here, over plates of crispy lamb ribs and charred broccoli, but it would be a perfect site for a swoony romantic dinner or a solo meal with a book. (They’re especially great for anyone with food allergies or restrictions.) For the ultimate Old Boston experience, you should head to The Barking Crab, with its outdoor, waterside seating and vast heaps of ultra-fresh oysters, fried clams, steamed lobster, and other classic New England bites.

Where to stay: The Seaport has the highest concentration of hotels in the area and you can’t go wrong here. Hyatt, Westin, Intercontinental, Omni, Hampton Inn: All are brand new, with sleek, minimalist interiors, views of the dark, glistening water, and great amenities, including pools. The Marriott Residence Inn, with its stunning, sunlit atrium and huge, comfortable lobby is a particularly great option, suitable for families, couples, and solo travelers alike (they also take dogs).

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Back Bay

Redish Brown buildings reflected in the water along  Charles River Basin.
Back Bay neighborhood of Boston
Image: Getty images/denistangneyjr

Developed in the 1850s as a luxury enclave, the Parisian-style boulevards of Back Bay are lined with stately brownstones and huge, flowering trees. In other words: This neighborhood is gorgeous. Walking around, looking at the lovely buildings, is an activity unto itself.

But any visit to Back Bay should start at the beginning: Boston Common and the Boston Public Garden, two gorgeous adjoining parks that form the area’s eastern border, lined with stately walkways and statues. Parents: You might want to allot a whole day to these parks, as kids have to be pried out of the Common’s Frog Pond area, with its idyllic Tadpole Playground, carousel, and the pond itself, open for swimming in the summer and skating in the winter. In the Public Garden, visit the Make Way for Ducklings sculptures, then take a ride (or two) on the Swan Boats, as my family does every summer.

Locals definitely do all of the above, but nine times out of ten, if we’re heading to Back Bay it’s for one reason: Shopping. Definitely take the time to walk along Newbury Street, Boston’s main commercial thoroughfare. Near the Public Garden, you’ll find higher-end shops—Valentino, Chanel, but as you walk west, things grow more affordable and younger. Some places to stop: Alan Bilzerian, a local boutique with a rock star vibe; Jonquils, a tea shop with ornate Japanese pastries; Revolve, a fantastic consignment shop; kids love The Fairy Shop; teens love Opal & Oak, No Rest for Bridget, and the adorable Mure and Grand.

For a dose of caffeine, pop into Pavement, a local roastery, or The Thinking Cup. For a quick lunch, my family loves: Red White, a sublime ramen shop, GreCo (tip: order ahead online, pick up your food and eat outside; also, try the sausage), La Neta, for tacos, and Little Miss Cupcake, for dessert (they have gluten-free and vegan options).

Some non-shopping favorites of mine: The Boston Public Library, a marble, castle-like structure with glorious murals from Sargent, Purvis, and Abbey. (Tip: If it’s warm, bring your lunch and a book to the gorgeous courtyard, modeled on Rome’s Palazzo della Cancelleria.) And the Mapparium, a glowing, three-story high stained-glass globe, which you traverse on a glass walkway.

Where to stay: Back Bay is full of classic hotels, all lovely and refined, and, as with the seaport, you really can’t go wrong. I’m partial to the Lenox and the Eliot, for their very central locations, and very Boston feels. A more luxe option: The Newbury. And a wonderful less expensive option: The cozy Sheraton.

Joanna Rakoff
Joanna Rakoff is the author of the novel "A Fortunate Age", winner of the Goldberg Prize and the Elle Readers Prize, and the bestselling memoir "My Salinger Year". She's written for Vogue, The Atlantic, the New York Times, and many other publications. The film adaptation of "My Salinger Year", starring Sigourney Weaver and Margaret Qualley, is currently streaming. Rakoff's new memoir, "The Fifth Passenger", will be out in 2025. You can find her on Instagram @joannarakoff.