There is something quietly remarkable about a group of friends who refuse to let time and distance pull them apart. For six British men in their fifties, that stubborn loyalty takes the form of a pub crawl. They call themselves the Jolly Boys, and every year they travel from different corners of the UK to London for the same weekend in September. It began after they read a book about the capital’s most historic pubs and decided to visit them all. Once they had, they kept going. The pandemic forced a short pause, but they returned with even more enthusiasm, recently completing their ninth trip. Over the course of that long weekend, they drank in 35 pubs, taking their grand total to 205. The group is a wonderful cross-section of ordinary life: engineers Richard Moore, Karl Young and Dave Russell, hairdresser Jon Main, business owner Vaughan Williams and commercial manager Trevor Power. They are not celebrities or professional influencers. They are simply mates who made a pact. The date has become sacred. Every third weekend in September is set aside, and no exceptions are allowed. The men plan their lives around it, and their families know better than to interfere. For one weekend a year, they are not fathers, husbands or workers. They are the Jolly Boys, walking the streets of London with a map, a list, and a shared sense of adventure. It is an extraordinary achievement, but what makes it more extraordinary is the fact that they have turned it into a never-ending story. There is always another pub, another borough, another reason to gather again next year.
The latest trip contained a moment of pure magic. The group was invited into The Keys, a pub inside the 900-year-old Tower of London. It is run by the 35 serving Yeomen Warders, and only their personal guests are ever allowed to enter. Business Insider once suggested that it might just be the most exclusive pub in the world. For the Jolly Boys, it was a place they had heard about but never expected to see. Karl Young, 55, the engineer from Bakewell, Derbyshire, who painstakingly plans the entire weekend, says it took three years of letters before they were granted access. He still will not reveal who finally opened the door. “It is amazing. It is definitely regarded as one of the most exclusive pubs in this country. If you are into London pubs it is almost that mythical place that you might never get an invite to.” The occasion demanded respect. The dress code was strict: shoes, trousers, a jacket, a tie and a shirt. The interior was full of military history, with centuries of tradition hanging on the walls. The beer, surprisingly, cost half the price of any ordinary London pub. The group stayed for more than three hours and watched the Ceremony of the Keys, the ancient ritual in which the Tower is locked up for the night. It is hard to imagine a better setting for men who love London’s pubs. This was not just another pint. It was a private audience with history, a glimpse of a world that almost no one gets to see. They had written letters for three years, never knowing if it would work, and then suddenly there they were, standing at the bar inside one of the most famous and forbidding buildings in the UK. It was a reminder that persistence is often rewarded, and that some of the best things in life are still hidden behind old doors.
Every crawl has its rituals. The Jolly Boys always arrive on Friday and meet at the Betjeman Arms in St Pancras station, which has become the official starting point of their adventure. Karl has already done the hard work. He produces a full document route every year, mapping out every pub and working out how to move through the city without crisscrossing their own path. It is a serious logistical challenge, especially now that they have exhausted the obvious historic places. “We have probably run out of notably historic London pubs and now it is more a question of hitting a borough and working out how to get through it without crossing our paths,” he says. The group always orders a pint of Guinness. They have created a rule about it, because the stout is always good and its lack of carbonation makes it easier to drink steadily across a long day. There is something deeply reassuring in this repetition. It removes the need for decisions and gives the weekend a steady, familiar rhythm. The best pint they have found so far is at the Guinea Grill in Mayfair, but even a less perfect Guinness is acceptable when you are with old friends. The walk between pubs is as important as the pubs themselves. They talk about their jobs, their children, their health, the things that have happened since the last time they met. They tell the same stories and laugh at the same jokes. They complain about their knees and their hangovers, but they never suggest stopping. The planning, the walking, the cold pints, the moments of quiet and the bursts of laughter all combine into a weekend of pure friendship. It is a lads’ weekend away, but it is also something deeper: a shared project that gives their lives structure and meaning.
Over the years, certain pubs have become favourites. The Prospect of Whitby in Wapping is one of London’s oldest riverside pubs, with a history stretching back hundreds of years and a terrace overlooking the Thames. The Mayflower in Rotherhithe is another, named after the famous ship that carried the Pilgrims to America, and it still has the feel of a place where history is part of the furniture. Ye Olde Mitre in Holborn is tucked away down a hidden alley, originally built to serve the servants of Ely Palace, and it feels like a secret even in the centre of the city. These are not flashy modern bars. They are dark, atmospheric places with low ceilings, old beams, uneven floors and stories in every corner. This year, the Jolly Boys started their crawl in West Brompton and walked towards Central London, a route that allowed them to see the capital from a different angle. The standouts were The Antelope and The Hoop and Toy, along with The Keys. The Antelope is a classic London pub, the kind of place where locals gather and strangers are made welcome. The Hoop and Toy, hidden in a quiet residential street, feels like a discovery. The group are not merely collecting names; they are getting to know London in a way that few people ever do. They see the city on foot, at pub pace, noticing buildings and streets that would be invisible from a car or a Tube train. They are also documenting how pub culture changes and survives. Some places are crowded, others almost empty; some are ancient, some relatively new. The Jolly Boys take them all as they come. As Karl says, London pubs are absolutely the best in the world, and there are so many to go at that the mission is genuinely never-ending.
It is impossible not to be moved by Karl’s own description of the project. “I can’t believe we managed to do all of these. It is ridiculous really. It is something that takes a lot of planning but something that we all really love. It is not just for the drinking, it is more like a lads weekend away.” Richard Moore, 59, explained why the fixed date matters so much. “It’s the only way we can guarantee we are all going to be available. The third weekend in September is always booked out in our calendars. Wives can’t plan anything for that weekend – it’s our weekend.” There is a quiet defiance in those words. Adult friendships are fragile. They are eroded by busy diaries, by tiredness, by the endless obligations of work and family. The Jolly Boys have solved that problem by making their weekend non-negotiable. It is as fixed as Christmas or a birthday. Nothing else is allowed to take its place. It requires planning, compromise and a little stubbornness. But the reward is a friendship that has lasted for decades and shows no signs of fading. The group are already looking forward. Next year, they hope to visit the pubs in the Houses of Parliament, which is not easy to arrange. And the Saturday of next year has already been planned: 30 pubs in one night, with just half a pint in each. It sounds absurd, but for this gang, it is simply the next challenge. They have already achieved 205 pubs; 30 in a single night is just another page in a long and glorious story. The ambition has not dimmed. If anything, they are becoming more confident, more determined, more willing to knock on doors and write letters and see what happens.
At its heart, the Jolly Boys’ pub crawl is not really about beer. It is about friendship, memory and the determination to keep something beautiful alive. There is a deep comfort in knowing that, no matter what else changes, the third weekend in September belongs to them. They will meet at the Betjeman Arms, order their first Guinness, and set off once more through the streets of London. The city will have changed, as it always does. Some pubs will have shut, new ones will have opened, and the Jolly Boys will be a little older. But the ritual will remain. They have turned something ordinary—a pub crawl—into an extraordinary act of loyalty. They have given one another a reason to get on the train, to book the hotel, to look forward to something in a world that sometimes feels short on excitement. The total of 205 pubs is impressive, but it is not the measure of their achievement. The real achievement is that they have built a tradition that holds six busy lives together. When they are old, they will be able to look back not just on a list of pubs, but on a lifetime of shared jokes, arguments, memories and friendship. The never-ending pub crawl may never end, and that is exactly the point. The destination is not the last pub. The destination is the friendship itself. And as long as one of them is willing to plan the route and the others are willing to turn up, the Jolly Boys will keep walking, keep ordering Guinness, and keep proving that some things are worth protecting. Next year, they will do it all again, and then the year after that. There is no finish line, and they wouldn’t want one.
