On the Trail of Winston Churchill

England’s Churchill Trail Illuminates the Life of The World Leader who Inspired Darkest Hour

“History will be kind to me, for I intend to write it,” Winston Churchill predicted.

As one of World War II’s most revered victors, Sir Winston’s droll prophesy proved only partially true, for his story is still being written. In recent years, the cherub-cheeked Churchill has enjoyed a bit of a revival as screenwriters have added their two cents, scoring millions at the box office with two biopics: Churchill, starring Brian Cox, and Darkest Hour, for which Gary Oldman won a Best Actor Oscar statuette at the 2018 Academy Awards.

Winston Churchill, courtesy Blenheim Palace

Winston Churchill, courtesy Blenheim Palace

If these silver screen insights have sparked a desire to do a deep dive on the iconic UK statesman, there’s no better place to begin than England. Key sites around the country form what might be dubbed “the Churchill trail.” From his labyrinthine War Rooms to the baroque palace where he was born, visitors can take a closer look at his legacy—and perhaps still catch an ethereal whiff of Sir Winston’s cigar.

Read on for the scoop on must-see Winston Churchill attractions around the UK. 

The Churchill War Rooms and Museum

Down a discreet set of stairs leading under the government buildings of London’s Whitehall, past a sombre-looking bust of Churchill himself, you’ll find the subterranean headquarters where he helped lead the Allied powers to victory in World War II.

The entrance to the Churchill War Rooms, which lie beneath Whitehall in London.

The entrance to the Churchill War Rooms, which lie beneath Whitehall in London.

Set designers for Darkest Hour spent months studying this crowded warren of rooms in order to faithfully recreate their intense, claustrophobic atmosphere at Ealing Studios. Tiny bedrooms equipped with bunk beds and insufficient chests of drawers, an office chock-a-block with piles of papers and perhaps a dozen phones, a map room with graffiti depicting Hitler, arm raised in his typical salute—all remain as an eerie time capsule, preserved as they were when the war ended in 1945.

Churchill War Rooms office in London, England

An untidy office in the War Rooms.

At the end of one corridor lies what appears to be a toilet, with the lock reading “Engaged.” Rumour had it this was the only flushing toilet in the bunker and was reserved exclusively for the prime minister. In fact, it was a transatlantic telephone booth with a confidential hotline, established in 1943 in an erstwhile broom closet.

Recordings offer fascinating—and sometimes amusing—reminisces by those who worked here, including one of Churchill’s secretaries. Every morning, she recalled, “Having slept heavily for six hours to the roar of the air-conditioning on a narrow cot covered with army blankets…as one hurried up the stairs heavy-eyed in one’s dressing gown, one always seemed to meet the sprucest, most haughtiest, most glamorous officers coming the other way.”

Winston Churchill's onesie, on display at the Churchill War Rooms and Museum in London

Little known fact. Long before supermodels starting sporting them in Ibiza, Churchill was a fan of the onesie.

Next door to the War Rooms, in the Churchill Museum, you’ll find intimate personal artefacts, including one of Churchill’s signature bowler hats, a cigar, and a nightshirt. Wartime footage plays on one screen, while film of his funeral procession troops across another, depicting the devoted crowds who came to pay tribute to one of the most respected politicians in Britain’s history.

Blenheim Palace

Contrary to popular belief, Churchill wasn’t born with a cigar in his mouth, but with a silver spoon. As the grandson of the 7th Duke of Marlborough, he spent much of his youth at the sprawling, 18th century Blenheim Palace, which presides over a 2,000-acre estate in Oxfordshire.

Winston Churchill's ancestral home. Courtesy Blenheim Palace

Winston Churchill’s ancestral home. Courtesy Blenheim Palace

Blenheim’s permanent “Churchill Exhibition” features the room where he first entered the world on November 30, 1874, as well as the prime minister’s personal letters, photographs, some of his paintings, and excerpts from his most famous speeches.

The room where Winston Churchill was born. Courtesy Blenheim Palace

The room where Winston Churchill was born. Courtesy Blenheim Palace

A “Walk in Churchill’s Footsteps Trail” further outlines significant sites around the palace and grounds, including the chapel where he was baptised, the Temple of Diana where he proposed to his future wife, Clementine, and a memorial garden dedicated to Churchill in 2015 on the 50th anniversary of his death.

Temple of Diana, where Winston Churchill proposed to his wife. Courtesy Blenheim Palace

Temple of Diana. Courtesy Blenheim Palace

In the West Courtyard, a separate retrospective examines the parallels between Sir Winston and his ancestor, the 1st Duke of Marlborough, for whom Blenheim was originally built as a reward for his own military triumphs.


“A day away from Chartwell is a day wasted,” Churchill once remarked, expressing his great love of the peaceful Kent estate where he spent much of his time between 1924 until his death in 1965. Like the War Rooms, Chartwell has been left largely as it was during Churchill’s lifetime, complete with original furnishings, treasured photos and well-thumbed books, as if awaiting his imminent return.

Interior of Chartwell, home of Winston Churchill. © Jonathan Primmer

Chartwell interior, © Jonathan Primmer

A particular highlight of Chartwell is the Studio, which is filled from floor to ceiling with paintings by Churchill, a passionate amateur artist. These include portraits and a multitude of landscapes portraying Chartwell’s gardens and parklands as well as scenes from Churchill’s travels around the world. Pausing as you pass the chair where he once sat, paintbrush in hand, with a still-unfinished canvas on his easel, the great man’s presence is almost palpable.

Winston Churchill's paintings at Chartwell, © Chartwell/National Trust

Winston Churchill’s paintings at Chartwell, © Chartwell/National Trust

“When I get to heaven,” Churchill said, “I mean to spend a considerable portion of my first million years in painting.”

St. Martin’s Church

When Churchill died in January 1965 at the age of 90, the nation mourned. He was honoured with an elaborate funeral at St. Paul’s Cathedral, but he was actually laid to rest at a private service at St. Martin’s Church in Bladon, just 2.5 kilometres from Blenheim Palace. Visitors are welcome to pay their respects beside the grave which Churchill shares with his wife Clementine, who joined him there in 1977.

While the world grieved his passing, Churchill, at least, had no fear of death. “I am ready to meet my Maker,” he had insisted, years before his passing. “Whether my Maker is prepared for the great ordeal of meeting me is another matter.”


Where to stay: “My tastes are simple,” the eminently quotable Churchill once quipped. “I’m easily satisfied with the best.” It’s no surprise, then, that The Stafford London, a five-star boutique hotel steps from Green Park, is said to have been one of his favourite haunts.

Its refurbished American Bar was popular with U.S. servicemen during the war, too, and it was here that Nancy Wake, a British agent dubbed “The White Mouse,” exchanged intelligence with an American counterpart. She remained a frequent patron until her death in 2011, no doubt feeling at home among the bar’s extensive collection of American memorabilia. Drink a toast to the brave lady when you order “The White Mouse” cocktail—a blend of saffron gin, champagne, lemon juice, rosemary syrup and egg white–named in her honour.

The American Bar, courtesy The Stafford Hotel

The American Bar, courtesy The Stafford Hotel

There’s more history in the wine cellar below. While the caverns are now filled with rare and pricey vintages, during World War II, they overflowed with Londoners desperate to shelter from German bombs, and a few artefacts from the war still remain.

The Stafford's Wine Cellars, courtesy The Stafford Hotel

The Stafford’s Wine Cellars, courtesy The Stafford Hotel

Tourism information: www.visitengland.com; www.visitbritain.com


  1. nomipalony says:

    thank you Amy Laughinghouse!xx grace

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