Boston’s 6 most historic and best-loved attractions

Boston Skyline at Sunset

One of America’s oldest cities is now Thomas Cook Airlines’ newest destination. We went to meet the people behind Boston’s most historic and best-loved institutions

By Imogen Rowland

When a group of pilgrims set sail from Plymouth in search of a brave new world back in 1620, they probably couldn’t have imagined the place they rather predictably named “New England” as it is today. Nor would they have believed that, almost 400 years later, its capital city of Boston would still pay tribute to many of the events they lived through after they disembarked from the Mayflower. But then, as we discovered when we visited some of its most iconic attractions, Boston’s past is also its present, and its future.

1. The Boston Light

Lighthouse Boston Harbour

Lighthouse Boston Harbour

“When I was 10 years old I came to see the Boston Light for the first time, and told my parents that someday I’d be married here. Thirty-three years later I was, and now, after another 21, I live here, too,” laughs Sally Snowman, keeper of the oldest continuously working lighthouse station in America. “Growing up I used to say that Boston Harbour was my backyard – now it really is!”

Sixty-four-year-old Sally is the official caretaker of Little Brewster, one of the 34 islands scattered in Boston Harbour that form the national park, and home to the first lighthouse established in colonial America: the Boston Light, which first shone in 1716. “I started volunteering in the coast guard auxiliary 39 years ago,” she says. “My husband Jay was also a volunteer, and that’s how we met.”

The Boston Light was an active coast guard station until 2003, but as more staff were deployed to Boston port security, it was decided that the post should go to a civilian. To do that, the coast guard had to apply to change a congressional law which stated the light should always have an official presence and, once that was granted, write a 21st-century civilian lighthouse keeper’s job description. As the only civilian keeper in the whole of the United States it was a highly desirable role and Sally had to beat off stiff competition to win the post in 2003. But then, not many candidates can have shown greater passion.

“I’m here about 80 per cent of my life, even though I’m technically only paid for a 40-hour week,” says Sally. “But there’s so much to do, from maintaining the light station and the island to training and managing 70 volunteers, liaising with the park service, welcoming visitors…” Still, she rarely finds it stressful. “When I’m here, I go on to island time – it’s so peaceful, waking up with a lighthouse in the side yard, singing with the seagulls and dangling my feet off the dock of the tower to watch the sunset.”

Sally is the 70th keeper here, and the first ever woman, “after 299 years!” she exclaims, smiling. With 2016 marking the light’s 300th birthday, it’s something she is justly proud of – and she has no plans to give it up any time soon. “Retire? No! We had an old rescue dog, Sammy, who lived out here with us, until one afternoon a couple of years back he fell asleep on the lawn by the tower and never woke up. Boy, that’d be a nice way to go…”

Info: Tours to the Boston Light take place twice daily from Friday to Sunday, July to October, and cost around £26. bostonharborislands.org

2. The Freedom Trail

The Freedom Trail Sign, Boston

The Freedom Trail Sign, Boston

“Boston is a great city – it has so much history, but it’s kind of a grumpy history,” says Rob Crean. “We’re best known for having riots and protests, but then that’s why we played such an important role in the founding of America.” Rob is a tour guide on the Freedom Trail, a 4km route that takes in 16 sites pivotal to the Boston Tea Party, and the subsequent American Revolution.

Dressed in a traditional 18th-century colonial outfit, complete with white tights, tricorne hat and button-down jacket, the 37-year-old is a comedian by trade who began leading Freedom Trail tours five years ago. “I grew up here, but the history still excites me,” he says.

“I initially thought this would be a fun day job, something that would make me a better performer – but over the years I’ve realised that it doesn’t just support my art, it’s become part of it, and it connects me with people in a more meaningful way, entertaining and educating them at the same time.”

Starting on Boston Common – the oldest public park in America – the tour follows a marked route via the Massachusetts State House, the Granary Burying Ground (the graves of Paul Revere, Sam Adams, John Hancock, who were instrumental in the Tea Party rebellion, are found here), the Old South Meeting House, where the patriots decided to stage the tea rebellion in protest against the taxes being imposed by the British government, and ending at Faneuil Hall.

Throughout the tour, Rob is in character as Isaiah Thomas, who was the publisher of The Massachusetts Spy, a local newspaper with offices on the second floor of what is now the Union Oyster House. But his favourite character from the period, he says, is Paul Revere – the famous “midnight rider” who rode on horseback to warn fellow patriots of the approaching army forces at the start of the revolution. “And I guess I’m trying to follow in his footsteps,” says Rob, “spreading the word of our city’s history.”

Info: Tours with the Freedom Trail Foundation take 90 minutes and cost around £8. thefreedomtrail.org

3. Union Oyster House

Boston's historic Union Oyster House at Union Street

Boston’s historic Union Oyster House at Union Street

“Not many restaurants can boast that they’re a designated national historic landmark. In fact, only one in the whole of the United States can: ours,” says Joe Milano, smiling. “We’ll turn 190 years young in 2016.” The Union Oyster House on Union Street, in the heart of Boston’s historic centre, opened its doors in 1826 and has been serving New England oysters and lobsters (“still our best-sellers”) ever since.

Joe, 71, co-owns the restaurant with his sister, Mary Ann, 72, and together they are only the third family to run the establishment. “I’m a Vietnam veteran, and when I left the army I wanted to get into the food industry,” says Joe. “We came in as partners with the previous owners in 1970, and then took full control in 1974. Since then we’ve expanded the restaurant into the neighbouring building and added a liquor bar, but the original features like the curved oyster bar are still there. Even our dumb waiter [food lift] is 110 years old!”

The restaurant’s reputation has brought in hundreds of recognisable faces, perhaps most famously the Kennedy clan. “JFK came here regularly, always requesting a particular booth, number 18, on the first floor. After he died his family came for dinner and we dedicated it to him. To this day, the Kennedy Booth is considered the best seat in the house: people still file past it to take a picture of the plaque. Last week one of them was Barack Obama, who dropped by for a cup of clam chowder while he was in town for a Labour Day conference. You should have seen the faces of the people in the Kennedy Booth when he appeared,” says Joe, laughing.

Maintaining an institution like the Oyster House is a challenge, Joe explains, not least because on its busiest days the restaurant has been known to feed 3,000 customers. “We deal directly with oyster farms because we get through so many of them – and our lobsters come from wholesalers. The food industry is all about provenance now, but that’s no issue for us: we serve true New England fare.”

As for the future, Joe hopes that one of his four daughters may some day take over the business, “But they’re all very independent. If they don’t, I will have to care very strongly about the new owners to sell the business to them,” he says. “Boston is very unusual, so historic, and we’re parochial – it’s really hard to break into a New England market – so there has to be trust, and there has to be a relationship. That’s why we’ve been going so long.”

Info: unionoysterhouse.com

4. The Boston Tea Party Ships and Museum

Tea Party Ships & Museum in Boston

Boston Harbor and Financial District at sunset and Tea Party Ships & Museum in Boston, Massachusetts

Brits take their tea seriously, but you could argue that Bostonians are even more obsessed. Because it was tea – or the taxes levied on its import (and other goods entering the country) – which was the catalyst that sparked the American Revolution and the subsequent Declaration of Independence, when the USA officially cut its ties with the British Empire in 1776.

“To protest against unfair taxes, the Sons of Liberty, along with hundreds of other colonised pilgrims, stormed three ships docked in Boston Harbour on 16 December 1773, pouring their contents – 92,000 pounds of tea leaves – into the sea,” says Evan O’Brien, the creative director of the Boston Tea Party Ships and Museum.

“It was dubbed the destruction of the tea, and it was the event that marked a change in relations between the Empire and the colonial settlers, putting figures like Paul Revere on their quest for independence in earnest. That tea was worth $1,700,000 [£1.16 million] in today’s money – the Brits were not pleased!” he laughs.

Evan’s role is to tell the story of these events in an entertaining way. He’s instrumental in making sure that the museum is anything but boring, creating an immersive theatrical experience by casting visitors into the roles of the real-life patriots who took part in the protest, and walking them through the story: first joining a disgruntled town meeting, then boarding one of the ships and throwing the tea overboard, before uncovering the events that followed through projected holograms, film and portraits that come to life. “It’s first-person, interactive storytelling, so our staff all portray people who were part of the protest,” says Evan. “They’ve even researched the life stories of these people, and the language and dress of the time. Ultimately, we can’t change the story – the facts are the facts, the characters are the characters – so instead we use technology and modern techniques to bring the story to life for a modern audience.”

An arts college graduate, 34-year-old Evan was born in the city and says he has always been passionate about its role in US history. “This is quintessential Boston, but it’s also iconic America,” he says. “If these Bostonians hadn’t done what they did the revolution may not have even taken place. So all of the civil liberties we enjoy today – all of the things we take for granted – are thanks to those people who stormed the ship, who stood up and gave the people a voice.”

Info: Tickets for the Boston Tea Party Ships and Museum cost around £16. bostonteapartyship.com

5. Harvard University

Harvard University

Harvard University’s campus in Cambridge, MA

“What do Harvard and Yale students have in common?” asks Cormac Conners as he stands in front of Mass Hall in Harvard Yard. “They all applied to Harvard!” he laughs. The 19-year-old from Milton, just south of Boston, is an economics sophomore [second year] and in his spare time works as a guide leading groups of tourists on the so-called Hahvahd Tour.

“Bostonians don’t pronounce their ‘R’s, so we end up sounding a bit Australian,” he explains. While the rivalry between Yale and Harvard is as deeply ingrained as it is between Oxford and Cambridge, there’s no question which of these American institutions came first: Harvard is the US’s oldest university, founded in Cambridge (no, not that one) in 1636, just 16 years after the Mayflower arrived. Some 380 years on, Harvard is still the most famous university in America, and has schooled everyone from presidents such as John Adams, Theodore and Franklin Roosevelt, and JFK, to celebrities like Natalie Portman and Conan O’Brien. But graduating isn’t essential. “Some drop-outs are equally renowned,” says Cormac. “Bill Gates, Matt Damon and Mark Zuckerberg once walked these halls, and last time I checked they weren’t doing badly.”

Wearing the university’s trademark crimson T-shirt and a straw hat, Cormac leads around seven of the company’s 90-odd tours a week, departing from Harvard Square and leading visitors through the campus gates into the leafy yard, past the John Harvard statue, via the Memorial Church where graduation ceremonies are held, and on to Annenberg Hall, an old cathedral where freshmen [first years] dine. Cormac’s enthusiasm for the place, and its legends, is infectious. “I probably came here for the wrong reasons; because of Harvard’s name and status,” he says. “But what makes it so awesome is the people. My classmates amaze me on a daily basis. And the history is so incredible – it’s kind of crazy to be walking down a hallway and think, ‘Oh, that’s where Teddy Roosevelt used to live.’ I love sharing those stories with visitors, and they seem to like it, too. Plus, they can leave saying they’ve been to Harvard. You don’t get that on a Yale tour…”

Info: Hahvahd Tours run several times daily and cost around £7. trademarktours.com/harvard-tour

6. Fenway Park

Fenway Park

Night baseball game at historic Fenway Park, Boston Red Sox, Boston, Ma

It takes a serious fan to describe a sports ground as being “a Mecca of sorts”, but that’s what Rob Blomberg says of Fenway Park, home of the Boston Red Sox baseball team.

“People in Massachusetts don’t even know how to spell ‘socks’ the right way, we’re that devout!” he says as he leads a tour group around the ballpark, through the bleachers, via the press box and up to the famous “Green Monster” scoreboard. Semi-retired Rob, 60, started working at the ground a year ago, after a 38-year career in insurance, but his time as a Red Sox fan eclipses even that. “I first came here with my grandparents when I was five,” he says. “I’ve had season tickets since 1978 and I’ve watched hundreds of games here. The best had to be game six in the 2013 World Series – we won our first championship at home since 1918, and the atmosphere was totally electric.”

Whether you’re a baseball fan or not, touring Fenway Park, just west of the city’s Back Bay area, is considered by most to be a must-do when visiting Boston. The oldest ballpark in the Major League, it’s 103 years old, having first opened in 1912, “But it’s never looked better,” says Rob, whose 23- and 21-year-old sons join him here on match days. “The grounds crew do an immaculate job of maintaining the field,” he says, pointing out a group of people staring fixedly down at the small but integral pitcher’s mound in the centre of the diamond-shaped pitch, “and everyone is just thrilled, honoured, to work here.”

When it’s at capacity, Fenway Park can hold just short of 40,000 spectators per game, but it feels more intimate than that, something Rob attributes to the soul of the place. “You really have to come and watch a game to understand it properly. The Red Sox are the heart of Boston. When we won the championship in 2004 church bells tolled throughout New England… we have a long and proud history, but we’re also part of the city’s future – and, based on our up-and-coming players, that future’s bright. I predict a World Series championship within the next few years,” he says proudly. “So you’d better keep your eye on the ball.”

Info: Tours of Fenway Park run daily and cost around £12. boston.redsox.mlb.com

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