A tour of the city that JFK called home

John and Jackie Kennedy with their children John and Caroline at their family home in Hyannis Port in 1962 - Credit: Ken Hawkins / Alamy Stock Photo
John and Jackie Kennedy with their children John and Caroline at their family home in Hyannis Port in 1962 - Credit: Ken Hawkins / Alamy Stock Photo

John F Kennedy always thought of Boston as his hometown. When the Secret Service recovered the monogrammed wallet from his bloodstained jacket on November 22 1963, the address on the driver’s licence spoke volumes: 122 Bowdoin Street, Boston.

Kennedy planned to move his family back to Boston, the city which first propelled him to greatness, once his four or eight years in the White House were over. Sadly, fate – and an assassin on the sixth floor of a Texas book depository – had other ideas. 

Monday marks the centenary of the birth of one of the most popular presidents in US history, and his hometown (JFK was born in Boston’s Brookline district at 3pm on May 29 1917) is celebrating with a flurry of special events and new exhibitions. 

The John F. Kennedy Statue by Isabel McIlvain, Massachusetts State House, Boston - Credit: Alamy
The John F. Kennedy Statue by Isabel McIlvain, Massachusetts State House, Boston Credit: Alamy

The excellent Kennedy Walking Tour weaves together nine key sites from the president’s life in the course of 90 minutes. It’s an excellent way to familiarise yourself with downtown “Beantown”, as Boston is known, so I sign up and meet my guide – local historian David – in front of the JFK statue on the State House lawn.

“They called Kennedy the first Irish Brahmin, because he was the first guy from a Catholic, immigrant background who really succeeded in challenging the political elites here,” says David. “He was an exceptional individual who just kept proving himself time and time again; repeatedly overturning odds.” 

From the State House we stroll in bright New England sunshine on to nearby Bowdoin Street, where JFK maintained his Boston apartment, even after marrying Jacqueline Bouvier in 1953, and moving to the White House in 1961. Next door, the “gentlemen’s hotel bar” he frequented as a bachelor has evolved into an appealing gastro-pub – The 21st Amendment. “JFK wasn’t a particularly big drinker, but he would come here regularly – usually to one of the window booths, with family, friends and advisers to dream about and plan his political rise,” says David.

The Omni Parker House in Boston - Credit: Alamy
The Omni Parker House in Boston Credit: Alamy

Central Boston is peppered with JFK hotspots like this, from Old City Hall – where his idolised grandfather John “Honey Fitz” Fitzgerald worked as city mayor – to the campaign headquarters for his own successful applecart-turning Senate run in 1952. 

A few minutes’ saunter later, we find ourselves entering another building steeped in Kennedy lore: the Omni Parker House Hotel at the foot of Beacon Hill. It was here that a six-year-old JFK made his first public speech while standing on a table at his grandfather’s birthday party, then – 23 years later – announced his own 1946 run for Congress. It was also here, at table 40 in the hotel’s restaurant, that he proposed to Jackie in June 1953, then held his infamous stag party. 

Our walking tour finishes at JFK’s favourite restaurant: Union Oyster House, where the up-and-coming orator could be found most Sunday afternoons, sitting in the same booth, dissecting piles of newspapers over steaming bowls of lobster stew. 

The Oyster House is putting some of Kennedy’s favourites back on the menu to celebrate his centenary and you can enjoy them in the Kennedy Booth (no 8) if you book in advance. Here, at the oldest continuously operated restaurant in the US, you can gorge on some of the finest seafood in New England, pondering not what Americans could do for their country but what another plate of delicious Bluepoint oysters could do for you.  

Boston’s two flagship Kennedy museums are celebrating the president’s 100th birthday with new exhibitions – and both are a short subway ride from the city’s walkable core. The John Fitzgerald Kennedy National Historic Site is the official title of the painstakingly restored Kennedy family home at 83 Beals Street in leafy Brookline, now run by the National Parks Service. JFK was born in the master bedroom on the first floor, and the house is full of original touches, from the children’s personalised breakfast bowls to Jack’s favourite storybook sitting on a wooden chair next to his bed: King Arthur and the Knights of the Round Table. (Proof, if any was needed, that the Camelot myth followed him throughout life). 

For the centennial celebrations, the museum has produced a special video exhibit: “John Fitzgerald Kennedy The First 100 Years”, including rare family footage, which opened last week and will run until the autumn. 

The Old City Hall in Boston - Credit: AP
The Old City Hall in Boston Credit: AP

At the other end of town, the grand John F Kennedy Presidential Library and Museum at Columbia Point overlooks Boston Harbour, into which all eight of Jack’s great-grandparents sailed in the 1840s, escaping Ireland’s potato famine. The starkly geometrical repository was designed by IM Pei, the brains behind the Louvre. Next week it opens its own exhibition – JFK at 100: Milestones and Mementoes. 

The collection includes 100 personal artefacts from the president’s life, many of which have never been displayed before. Numbered 1-100, they include JFK’s handwritten notes for his landmark civil rights address, ahis iconic sunglasses, and pictures drawn for him by his children.

“JFK is such a looming historical figure that it’s often difficult for people to get an impression of him as a normal person,” says Stacey Bredhoff, the museum’s curator. “That’s what we’re trying to do here: present Jack the man as well as JFK the president.” 

Boston harbour - Credit: LindsayBuckley
Boston harbour Credit: LindsayBuckley

For a man who was president for a little over 1,000 days, JFK’s farseeing, compassionate leadership – personified by his sweeping Civil Rights Bill and championing of the arts – left an enduring legacy, which Boston intends to celebrate in style. 

The words from Kennedy’s own inauguration speech, chiselled into the marble walls of the JFK Library, sum it up best: “All this will not be finished in the first one hundred days,” the young president told his nation. “Nor will it be finished in the first one thousand days, not in the life of this administration, nor even perhaps in our lifetime on this planet. But let us begin.”

Essentials

America As You Like It (020 8742 8299; americaasyoulikeit.com) offers a four-night holiday to Boston from £799 per person, including return flights with Norwegian from London Gatwick to Boston and four nights room only at the Omni Parker House Hotel.

To plan your visit to Boston, see boston usa.com

Further information about centennial activities across the US is available online at jfkcentennial.org/events/ or via social media using the hashtag #JFK100