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Boston city guide: where to eat, drink, shop and stay in the east coast’s cosiest city

With elegant brownstone neighbourhoods, character-packed craft beer joints and lashings of history and culture, this handsome city is a down-to-earth delight, says Nicola Brady

Thursday 09 December 2021 20:04
<p>Boston’s South End neighbourhood in spring</p>

Boston’s South End neighbourhood in spring

While Boston packs a fair punch when it comes to historical sights, it’s no longer a city just for Harvard, tea parties and the Red Sox. Infinitely walkable, you can lose yourself for hours wandering between the up-and-coming neighbourhoods, ducking into dive bars and coffee shops along the way.

Plus, with a short flight time and an airport just 10 minutes from the centre, you couldn’t ask for an easier city for a long weekend spent stateside.

What to do

See the sights

Get acquainted with the city (and its history) with a stroll along the Freedom Trail – tours $16 (£12) – a series of landmarks linked with a narrow line of red brick that makes self-navigating a breeze. You’ll pass by 16 sites that tell the story of the revolutionary history of the city, from the pretty Boston Common (America’s oldest public park) to the Old South Meeting House, where the Boston Tea Party began.

Afterwards, take a wander through the Rose Kennedy Greenway (free), a mile and a half stretch of skinny parks filled with rotating contemporary art exhibitions. Just over the bridge, you’ll find the Seaport District, a cool neighbourhood that blends gleaming skyscrapers with pretty harbourside views and excellent shopping. It’s also home to the Institute of Contemporary Art ($15).

Paintings in the Museum of Fine Art

Go museum hopping

In Beacon Hill, the Museum of African American History ($10) is set in two landmark buildings – the oldest Black church building in the country, and the first public (state) school for African American students. Both are featured on the Black Heritage Trail, which you can follow on a self-guided tour on the free National Parks Service app.

Down towards the Fenway neighbourhood, the Museum of Fine Arts ($25) is home to a sprawling collection of art from all over the world, including some famous van Goghs and a sprinkling of Egyptian artefacts. Just around the corner is the Isabella Stewart Gardner Museum ($20), both an excellent art museum and the scene of the world’s single largest property theft. A total of 13 pieces of art were stolen in 1990, with some paintings cut right out of their frames, which remain empty on the walls of the Dutch Room.

Stroll the neighbourhoods

The pretty Boston district of South End is perfect for an afternoon stroll, where you can wander the side streets and fantasise about owning one of the dreamy townhouses. The brownstones and redbrick rowhouses that line these streets are the epitome of Bostonian charm, and the owners of the stoops seem to be in a perpetual state of competition when it comes to seasonal decorations. And if you can’t pass a dog without saying hello, you’ll be in heaven – it seems like every other passerby is walking a pup, and the neighbourhood is filled with dog-friendly bars and hound-themed boutiques.

A room at the Liberty Hotel Boston

Where to stay

Right in the heart of Beacon Hill, The Liberty Hotel was once the Charles Street Jail, and the inner courtyard is a masterpiece – octagonal in shape and flooded with natural light. While the rooms only have subtle nods to the building’s history, the Clink bar is set in the former cells. Doubles from £169, room only.

If you want to make your base in cool South End, The Revolution is a great choice. With an artsy lobby and loft rooms that feel like having your own chic East Coast apartment, this is the perfect spot for a homely, neighbourhood vibe. If you’re on a budget, there are also cosy bunk rooms with shared bathrooms. Doubles from £50, room only.

With a cool rock’n’roll motel aesthetic, The Verb in Fenway is one of the hippest stays in town. Rooms come with their own record player and speakers, and there’s a huge library of vinyl onsite, as well as a heated pool. Doubles from £104, room only.

The Boston skyline

Where to eat

Unsurprisingly, Boston is big on seafood. Once you’ve had your fill of lobster rolls and chowder, head to Select Oyster where you’ll find locals propping up the bar with a glass of cava and the ceviche of the day – think barracuda with tart green apple, or yellowtail crudo with crispy ginger and a zingy passion fruit.

Down in South End, B&G Oyster has plenty of east coast oysters served fried or on ice, but they’re better known for their lobster BLT, a towering sub that arrives packed with huge chunks of lobster and crispy bacon (and seasoned fries).

If you’re short on time, the Time Out Market in Fenway has all the best Bostonian eats under one roof. Go hungry – or with people willing to share – and you can tuck into any number of local delicacies, such as the sandwiches from Cusser’s piled high with slices of rare roast wagyu beef and spicy aioli, or fried chicken and dumplings from Ms. Clucks. There are bars, too, so don’t miss sampling some of the local beers – there’s even a local kombucha on tap.

Seafood at Select Oyster

Where to drink

Boston is a beer town through and through, with a glut of local dive bars and breweries. There’s a great selection over in the Cambridge neighbourhood, where you’ll find students from Harvard and MIT sharing pitchers or refilling their growlers. The taproom at Lamplighter Brewing Co is open every day, and they serve flights and draft pours of their own lagers, pale ales and sour beers, alongside killer bar snacks like soft pretzels and truffle popcorn.

Just down the road, the brew pub Lord Hobo always has a great selection of IPAs on tap but a few cocktails to keep things interesting – try the lavender whiskey sour for a nightcap with a bit of pizazz.

If you’re looking for a caffeine jolt, you’ll find a branch of Tatte Bakery and Café in almost every neighbourhood – the sight of their mosaic floors and Parisian-style awnings is always welcome when you’re gagging for a coffee and a sit down.

Where to shop

The pretty brownstones along Newbury Street are filled with independent boutiques and the smaller US stores we love to visit, like Madewell, Reformation and Gorjana. Things get a little less mainstream the further towards Massachusetts Avenue you head, and there are plenty of coffee shops and juice bars along the way. If you want a proper pitstop, head down to Trident Booksellers, part rambling bookshop and part café/wine bar, where you can browse the excellent curation of books before sitting down for a glass of red and a grilled cheese (open every day).

Speaking of bookstores, Brattle Book Shop is a dream for bibliophiles, with three floors of rambling shelves filled with secondhand books and rare first editions. In the empty lot next door, there are shelves stocked up with bargain titles, so you can browse al fresco and come away with a stack of books that only cost you a dollar apiece.

Architectural highlight

The main branch of the Boston Public Library in Copley Square is an architectural marvel, with intricate mosaic ceilings and limestone staircase embedded with fossils.

Acorn Street, Boston

Nuts and bolts

What currency do I need?


What language do they speak?


Should I tip?

Between 18 and 20 per cent.

What’s the time difference?

Boston is five hours behind the UK.

How should I get around?

If you’re staying fairly central, you’ll get to most places on foot. If you want to travel further afield (or don’t fancy so much walking) then the subway (known as the T) is quick and reliable – just buy a one-day “Charlie Ticket” from any station ($12.75), or pay per journey ($2.40).

What’s the best view?

Grab a cocktail or a bowl of olive oil gelato at the rooftop bar Contessa, for a gorgeous view of Boston Common and the city beyond.

Insider tip?

If you’re around on a Sunday, the SoWa Vintage Market is held all year round and is a treasure trove for antiques, jewellery and clothing.

Getting there

Trying to fly less?

The QM2 cruise ship runs between Southampton and New York (a 3.5-hour drive from Boston) 12 or 13 times a year; or take a cargo ship such as Atlantic Sail from Liverpool to New York, via Halifax.

Fine with flying?

All the major transatlantic airlines – eg BA, Delta – have flights between London and Boston.

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