Best places to shop in Boston

Charm, pedigree and a tinge of old-world European flair – in Boston, history fuses with unapologetic individuality to create a shoppers' paradise, stretching from the cobblestoned elegance of Beacon Hill to the lively stalls of Bow Market. Best of all, the city’s walkability makes it easy to plan a shopping expedition that spans every corner, even if you’re short on time. With our curated list of retail destinations in hand, slip into your comfiest shoes, breathe in the salt air and dive into Boston’s vibrant, irresistible shopping scene.

Bow Market 

This hive  of micro-sized indie shops in Somerville’s Union Square, selling everything from rare board games to offbeat vinyl, is a magnet for Boston’s hipster contingent. Immerse yourself in books and magic at the queer-friendly Side Quest Books & Games, peruse dapper menswear at Blue Bandana Relics and chat to the gregarious shopkeepers at card and stationery haven Tiny Turns Paperie. Afterwards, unwind at Bow Market’s open-air food courtyard, which offers delicacies from around the world – think bento boxes, Venezuelan bites, cocktails and macarons.

SoWa Vintage Market 

SoWa Vintage Market is a treasure trove of estate jewels, funky furnishings, and fashion finds, including tiaras, boas and sky-high heels. This rollicking bazaar is held every Sunday inside a 19th-century redbrick warehouse in Boston’s art-and-design-forward South End. It’s easy – and encouraged – to lose yourself among the stacks. Once outside, wander the adjacent South End Open Market, lined with food trucks, art galleries, and stalls from local artisans selling handmade wares from soaps to jewellery.  

Charles Street 

Boston’s Beacon Hill is a neighbourhood of cobblestone streets, grand brick rowhouses, and storefronts that seem to have been around for centuries (some, indeed, have). Forming the spine of this landmark district is the elegant Charles Street, home to a medley of upscale boutiques. Find of-the-moment reads at Beacon Hill Books, browse au courant fashion and chunky jewels at December Thieves, shop like a discerning local at Fabled Antiques and step back in time at Charles Street Supply, Boston’s oldest hardware store and a beloved neighbourhood fixture. 

Newbury Street 

This stylish, brownstone-lined thoroughfare is Boston’s answer to Fifth Avenue or Rodeo Drive – with a blend of homegrown charm. Alice + Olivia, Armani, Le Labo, Tiffany & Co., and Valentino share real estate with beloved local restaurants including Stephanie’s on Newbury (sit outside for prime people-watching) and JP Licks (Boston’s favourite ice cream parlour). End the day at The Newbury; this luxury hotel is home to the rooftop Italian destination Contessa, where stylish denizens wedge designer shopping bags into sumptuous booths and savour skyline views. 

Seaport 

Boston’s newest neighbourhood, Seaport  is a rapidly developing maze of gleaming luxury skyscrapers, manicured green spaces, high-end chains and imaginative local enterprises. Year-round, the waterfront district hosts pop-up markets with a topical theme – such as women-owned businesses or retro and nostalgia-inspired wares – complemented by food, entertainment and activities like al fresco yoga. Among the pop-ups, you can also find permanent, longtime favourites including Anthropologie and L.L. Bean.

Harvard Square 

On the doorstep of Harvard University, Harvard Square  is Boston’s intellectual centre, offering a mix of established shops and quirky finds. Notable picks include Lovestruck Books, a shop dedicated to romance novels with a wine and coffee bar; the near-century-old Harvard Book Store, which regularly hosts big-name and local author talks; Cardullo’s, a must for gourmet food and wines; and Leavitt & Peirce, a neighbourhood institution offering elegant tobacco pipes, ornate chess sets and other ephemera. After a long day of shopping, duck into Mr Bartley’s Burger Cottage for a traditional milkshake and towering sandwich, known to have cured many a Harvard scholar’s hangover.

The North End 

Boston’s Italian enclave, the North End is known for fabulous restaurants, but it also boasts an array of must-visit shops, from Loft & Vine, stocking clever gifts, to Heart & Sole, a fashion-forward men’s boutique. After strolling the neighbourhood, turn the corner to discover Boston Public Market . Here, you’ll find a labyrinth of stalls run by local artisans, chosen for their originality and sense of place. Browse spices from Curio; crystals and plants from Happy Cactus; rustic serving dishes from Peterman’s Boards and Bowls; and much more – including fresh fruits, vegetables and locally made beer and donuts.