Pack Your Shoes for Boston’s Best Walking Tours

It has been the setting of some of the United States’s historic moments and has a tough reputation from its starring turns in gritty films. But to get to know the real Boston, you have to walk the talk. Lance Richardson takes three tours into its beating haaht.

The North End tour 

The North End in Boston, Massachusetts, is a world unto itself: small and densely packed with so much European charm that it could be in Southern Italy, where many of the residents historically come from. “We want to look back at what they were eating then,” says Beth Applebaum, standing on a street corner at the neighbourhood’s outer edge. I’ve joined a North End Market Tour guided by Applebaum, a retired high-school teacher, who’s here to make sure nobody leaves hungry.

The North End is all of one square kilometre yet, without an expert guide, it can be a little overwhelming. Who has the freshest panettone? The best Sicilian cannoli? Often, as Applebaum shows us, it’s not where you think. 

At the end of a nondescript alley with hardly any signage, a staircase leads down to a panetteria. “Originally, the baker’s idea was to make bread for his restaurants,” says Applebaum, “but the smell started wafting out.” The bakery, behind Bricco Ristorante, has nothing but a small bench and a list of ingredients scrawled on the wall: sale marino, acqua, olio d’oliva. But that’s Italian cuisine in a nutshell: simple ingredients treated reverentially.

Applebaum is an engaging, eagle-eyed host who’s full of bizarre and intriguing trivia. In a salumeria, she passes around spoons so we can all sample balsamic, explaining that sometimes in Italy, vinegar is made when a baby is born then included as part of a woman’s dowry. At Maria’s Pastry Shop, she points out crunchy ossa dei morti (“bones of the dead”) cookies and tells us that tiramisù means “pick-me-up” for its combination of sugar and coffee. A local greengrocer is introduced personally (“People go in and sit down to kibitz with him”) and a pizza chef walks up and hands Applebaum several slices, smiling warmly with recognition. It’s like being shown around town by a cousin who knows everybody.

“If you only see the tourist street [Hanover], you don’t see anything,” says Applebaum, leading us into a liquor store for shots of the herb-based liqueur Vecchio Amaro del Capo. You also won’t see how the United States retains strong links with the Old World; that there are entire neighbourhoods holding on to traditions.

“The world is full of fancy things now,” Applebaum says, raising her glass. “Nothing is real! But this is real.”

Boston Food Tours: North End Market Tour
Price: $US60 (about $79)
Duration: Three hours
Frequency: Various times on Wednesday,
Friday and Saturday; advance ticket required
bostonfoodtours.com

SEE ALSO: One Perfect Day in Las Vegas

The Harvard tour

Across the Charles River in Cambridge, the US’s most famous university sprawls like a labyrinth of red brick. Few institutions have the financial endowment of Harvard – and it shows. The campus is beautiful and meticulously maintained, with stately buildings and tree-lined squares. It’s easy to wander at your own pace – the university offers self-guided itineraries online – but to get a true understanding of what makes this place so hallowed, it’s best to join a student-led walking tour.

My guide is Danielle, a fast-talking doctor-in-training who power-strolls with a cup of coffee as though she’s late for her next biology class. To simply keep up with her is to get a good insight into what it means to study here.

Heading through Harvard Square, Danielle details the history of the university, its ethos – students learn a little about everything and one thing really well – and even some of the controversies. Women at Harvard were originally members of Radcliffe College. When they graduated, they got Radcliffe diplomas, not Harvard ones. This separate-but-equal state of affairs continued until 1999. “If you ask me, that is strikingly late,” says Danielle, her lips pursed.

As you walk past windows, it’s hard not to feel a little envious when Danielle says, “Matt Damon lived there; Natalie Portman was there.” Harvard has more than 70 libraries with 80 kilometres of books. There are 42 varsity sports teams. Every year, Harvard College offers 3500 undergraduate courses. There is a massive telescope that students can use and one lecture hall is modelled after Shakespeare’s Globe Theatre.

There’s also a romance about Harvard. It kicks into high gear in the late-afternoon light of autumn, when mountains of yellow leaves blow between the dormitory blocks. I find myself contemplating a master’s degree just so I can sit under a tree in a crimson sweater bearing the university’s logo.

One revelation comes as a shock: no film has been shot at Harvard for more than 40 years, not even Legally Blonde or The Social Network. In fact, the last one was Love Story (1970), which portrayed the students as decadent hippies – a smear that, adds Danielle, many here have still not forgiven.

Towards the end of the tour, somebody having the same higher-education daydream as I asks Danielle how much it costs to study here. The answer is many, many thousands of dollars, though our diplomatic guide is quick to point out that “20 per cent of the college students pay for nothing, through financial aid”. What about the other 80 per cent? I’m too nervous to ask so I just keep walking.

Harvard University: Guided Historical Tours
Price: Free
Duration: One hour
Frequency: Most days (check online calendar); advance booking recommended
harvard.edu

The Freedom Trail

You step out of the visitors’ centre on Boston Common into a forward-looking metropolis that slows down for no-one. But history is never far away. At your feet is a bright-red line snaking off through trees and high-rises. It’s The Freedom Trail: a four-kilometre self-guided walking tour that grafts the past onto the vibrant present by showing you what is and what was simultaneously.

Here, for example, is the Massachusetts State House – “the hub of the solar system”, as physician and poet Oliver Wendell Holmes Sr once called it – with its gilded copper dome that shines like a jewel (it starred in the final scene of Martin Scorsese’s The Departed). And there, nearby, is a knot of street performers heckling one another beneath a building with a dentist on the first floor and a psychic on the second. Such is the US, land of contrasts.

Indeed, The Freedom Trail, which can take a whole morning to explore, shows the full breadth of the world’s most powerful democracy. I visit a 19th-century Baptist church with an ivy-covered belltower, a graveyard surrounded by office blocks – resting place of the Patriots who rebelled against the British – and a fruit vendor who’s “been selling mangoes here forever”, a woman tells her friend. 

As well as the route’s 16 historic sites, there’s the living, breathing madness of America to contend with. Sometimes the combination makes for surreal tableaux. I watch an actor in 18th-century costume describe the Boston Massacre of 1770 to a crowd as a businessman stomps by, screaming into his smartphone.

The Freedom Trail will also lead you through Faneuil Hall, “the cradle of liberty”, with a giant grasshopper on its weathervane; and Quincy Market, where a hundred stalls will try to sell you clam chowder. But the best part of the tour is a restaurant: Union Oyster House (unionoysterhouse.com), established in 1826. The oyster bar is a real spectacle, with bartenders violently shucking Cotuit oysters and arranging cherrystone clams on beds of ice. I order a dozen, with Prosecco and crumbly cornbread.

“Salty? Good salinity?” the bartender asks a diner.

The customer nods then barks, with that unmistakable Bostonian accent, “Pass the horseradish!” 

SEE ALSO: One Perfect Day in San Francisco

Where to stay

Across the road from Boston Common is Boston Public Garden, which has a small lake and a statue of George Washington on a prancing horse. Just over another road, offering gorgeous views back through the greenery towards the gilded dome of the Massachusetts State House, is the Taj Boston. This hotel with 229 rooms and 44 suites is one of the city’s most convenient, as it’s close to pretty much everything of interest, from the theatre district to the Museum of Fine Arts. It’s also one of the city’s more elegant hotels, with a design aesthetic that recalls the White House – rooms with fabric wall coverings and wooden armoires. Taking high tea in the French Room is highly recommended and, during the warmer months, brunch is served on a rooftop terrace overlooking the city. Brunch includes, of course, a raw bar of Bostonian seafood.

A little closer to the sea itself is the Boston Harbor Hotel at Rowes Wharf. In fact, the hotel is so close to the water that it has access to a 34-slip marina, in case you want to arrive by yacht. All 230 luxury guestrooms have recently been renovated and many overlook the harbour – which is famous for the Boston Tea Party of 1773, when demonstrators dumped an entire shipment of tea into the ocean in protest at a new tax. To take advantage of the water’s proximity, have the hotel staff arrange a day cruise on the Charles River.

SEE ALSO: Two-Wheeled Tours of Hidden New York