“Bigger than Christmas,” says Larry the cab driver of the annual cricket match between the rival Bermudian parishes of Somerset and St George’s that has been contested on the islands since 1904. Few locals would disagree. The Cup Match is not only bigger than Christmas, it's also brighter, boozier and more bonkers, a two-day, rum-drenched fiesta that makes Saturday afternoon on the Hollis Stand look like a Mormon prayer meeting. And in the eye of the storm, grassy green iris, orange slit of a pupil, a nuggety lower order batsman is chiselling 28 off 46 balls.
Some history. On August 1, 1834 slavery was abolished across the British Empire, including the tiny North Atlantic islands of Bermuda. Emancipation Day became an annual celebration for Bermudian former slaves, and by the 1880s an informal cricket match had been incorporated into the festivities. (Cricket was introduced to the island by the British military in 1846.)
Playing for fun is great; playing for a big silver cup is even better – and so Somerset and St George’s raised 20 guineas to order such a trophy from England. The first official Cup Match was played in 1902 at Somerset’s Royal Naval Field; St George’s won by seven wickets. With the exception of 2020, the match has been played every year since.
I was lucky enough to be invited to the 2025 edition. What intrigued me – forget the beaches, the rum, the fried fish – what really intrigued me was the format. Both teams bat twice, no over limits, yet the whole thing is done in two days. How does that work? As everyone knows, a first class match typically stretches the same amount of cricket over four days – so either a draw was inevitable or the run rate must be astronomical.
A sensible forward defence amid all the silliness
A glance over past Cup Matches shows there are indeed a lot of draws. In recent years, there have also been a lot of Somerset victories – they won the 2024 match by the princely sum of 227 runs. Poor St George’s last managed a win in 2011. Since a draw means the holder retains the trophy, the drought is 13 years and counting. (Somerset went two decades without a cup win between 1959 to 1979 so sympathy will be minimal.)
Bermuda was quite intriguing, too. It’s technically an archipelago, made up of approximately 138 islands – the exact number varies depending on your definition of ‘tiny island’ versus ‘large rock’. The entire archipelago is 21 miles long and two miles at its widest point. Although a British overseas territory, the nearest landmass is Cape Hatteras, North Carolina some 640 miles to the west. A population of 64,000 is roughly equivalent to Torquay.
And the Bermuda Triangle, the region of North Atlantic Ocean that mysteriously swallows up ships and aircrafts? Urban legend. Sure, there was the odd disappearance back in the day but no more than you might expect – the ocean’s a big place.
Cup Match is as much about socialising as watching cricket. Or not watching cricket
Back to the cricket. The two parishes alternate hosting duties, the 2025 match being held at St George’s Wellington Oval. Since 1947, the match has coincided with a two-day national holiday. Emancipation is celebrated on Thursday; Friday used to be Somers Day, named after Sir George Somers, the English admiral who founded Bermuda in 1609. However in 2020, Somers Day became Mary Prince Day, commemorating the Bermudian-born enslaved woman whose 1831 autobiography helped pave the way for the Emancipation Act a few years later.
The match is underway when we arrive, queues stretching down the road. Fortunately there’s a fast-track option for VIPs and freeloading journalists. Once inside, the colours are almost overwhelming. Everything is ultra bright, popping, from the blue boundary walls to the green pitch to the bright red helmet worn by the Somerset opening bat. It's like someone's turned the saturation of the universe up to maximum setting. Beyond the ground, the ocean sparkles in the midday sun.
The Wellington Oval of St George's. We're not in Kennington anymore
Shades are a must; depending on your disposition, earplugs might also be welcome. The noise is quite something. Put simply, it's all noise. Music is blasted not only over the main sound system but also dozens of speakers around the ground. These speakers were brought by the spectators and while many of them are playing simultaneously it’s never the same track. Those without speakers compensate with a horn to be triumphantly blared at every boundary, wicket, over change and whenever the mood takes them. If the visual panorama is cartoonishly stimulating, the sonic landscape is a mixture of Caribbean nightclub and LA traffic jam.
The ground is ringed with temporary stands, many three storeys high and constructed primarily from scaffolding, girders and flags (including a West Ham United one – me neither). These stands are divided into various sections known as camps, most with their own bar and speakers, and everyone moves freely between them. Since the camps are divided by gauze netting or a flag, movement isn't very difficult – nor is it meant to be.
A scaffolding stand split into various camps – most with their own bar and speakers
On the field, the favourites Somerset start ominously, reaching 70 before losing their first wicket. It's a small outfield and the ball needs little encouragement to reach the boundary wall. The Somerset batsmen are in an encouraging mood nonetheless. St George field well but their bowlers, while competent enough, lack the necessary firepower, their medium pace doing all the damage of muskets unloading on warships. Often the result is cannon fodder from both ends.
Cricket is a bit like quantum mechanics: you either get it or you don't, and those who don't tend to be happy with their lot. The ground is divided into both camps, aka locals and tourists, most of the latter being American and therefore find a cover drive as mysterious as the wave function of an electron. But the match is very much secondary to the mixing (social and alcoholic). Most English cricket grounds have a designated party stand; the Cup Match is a party that happens to have a game of cricket occurring in the middle of it.
Zeko Burgess bowls to Somerset's red-helmeted opener Kamau Leverock. Even the headgear is colourful
All around the outer perimeter, dozens of food and drink tents do brisk business. The scent of fried fish is so potent you can almost taste the breadcrumbs. The pop-up Bacardi bar is notable for the lifesized inflatable elephant standing beside it. I say standing…something is amiss with its right foreleg so the poor elephant lists sideways in the manner of a mammal who's overindulged on the rum. I suspect it won't be alone come sundown.
My inspection of the intoxicated elephant is interrupted by a great commotion from the stands. (Granted the stands exist in a perpetual state of commotion but the horns are going even crazier than normal.) Streams of people are rushing onto the pitch. I ask somebody what happened. He's American and doesn't have a clue. “One guy made a certain amount of runs. I think.” The scoreboard confirms that the Somerset opener has reached his 50, a milestone that rarely produces a pitch invasion but they do things a little differently here.
By far the most popular spot is the giant white gazebo hosting multiple games of Crown and Anchor. Cup Match is the only opportunity for legalised gambling in Bermuda and people are understandably making the most of it. An old Navy game, Crown and Anchor is basically a simplified roulette. Lots of very excited people throw money onto various sections of a table and wait for the croupier to roll three dice. If your section is rolled, you win. Wellington Oval has no cash machines, which is probably for the best.
St George’s bring on a bowler whose muscular build would make Batman think twice. His name is Zeko Burgess and he’s fast, fast enough to cause an involuntary flinch of sympathy for the batsmen as the ball whizzes past their nose. One victim top edges, his successor is LBW next ball. Burgess ends with five wickets as Somerset are dismissed for 295. Some lusty hitting takes St George’s to 176-5 at close of play. Victory is possible for both teams – at least until a rainstorm wipes out the morning session. Such is life. Such is cricket.
Punters get stuck into a game of Crown and Anchor. Unsuccessfully, judging by the reaction
Unsurprisingly, the second day’s atmosphere feels a little flat when play finally resumes in the afternoon. With a draw all-but guaranteed, the main intrigue lies in whether St George’s No 4 Delray Rawlins, 76 not out overnight, can reach his maiden Cup Match century. He moves into the 90s with an extraordinary shot, flicking the ball off his pads to soar off over the stands. Apprehension is building. If a fifty causes pitch invasions, what does a century bring? I can't wait to find out.
Then tragedy strikes. On 98, Rawlins attempts a legside glance, only for the ball to bounce down onto the crease and back into the stumps. The Somerset fielders go berserk, the ground is a mixture of glee and disbelief. Rawlins stands there for 20, 30 seconds, motionless, trapped in a moment that will haunt his nightmares for the next few decades. A handful of spectators flock to him as he trudges off the field.
Oh Delray. Some motorboats look on, their sadness doubtless assuaged by the free seats
St George’s declare on 243, 48 runs behind Somerset, each team needing to bowl the other out for double digits to harbour any hope of victory. Condensing a first class match into two days cripples the chance of a positive result, requiring utter domination from one team or two equally hopeless batting lineups. Every Bermudian has a solution: start play earlier, extend the match to three days, limit the innings to 50 overs apiece. I spoke to multiple locals and found only one who claimed satisfaction with the status quo. (“It’s tradition!”) Naturally, there's no consensus on the best alternative.
The draw means Somerset retain the trophy for another year, thirteen and counting.. Unsatisfactory conclusion aside, I adored Cup Match. Noise, chaotic, joyful; a different type of cricketing experience than a Test at Lord’s but cricket all the same. Despite the abundance of rum, some memories still linger. A gigantic man on a camping chair playing Camptown Races on a black trombone. A lady in a designer dress and sunhat jogging along the side of the pitch to reach her friends. The motorboats parked on a dry stack berth beside the ground, their pointed bows peeking over the blue wall like interested spectators. Poor Rawlins staring at his ruined stumps.
The next generation warming up
A brief section on Bermuda
Cricket aside, Bermuda offers plenty to keep you occupied. The capital Hamilton is a very cool little city, and I really do mean little: you can walk the entire thing in less than an hour and its resident population of approximately 850 people makes it among the world’s smallest capitals, and indeed cities period. (The population is roughly the same as Vatican City; Ngerulmud, capital of the Pacific island Palau, only has a population of 400.)
Yet Hamilton crams an awful lot into what feels like six streets. On our visit, the Bermuda National Gallery was hosting exhibitions from renowned surf photographer Seth de Roulet and Andy Warhol (yes, that one). Down the road stands the Cathedral of the Most Holy Trinity, aka Bermuda Cathedral – built in the Gothic-style, the interiors are stunning and the tower can be climbed for $5. Directly across from the cathedral you’ll find The MarketPlace, equally spectacular in its own way: this grocery store contains every produce imaginable, including multiple food stations serving everything from sushi to jerk chicken to fried fish.
A few of the many islands that make up Bermuda. There are worse places to visit
All this exploring will bring a thirst; Bermuda has a surprising number of British-style pubs that manage a far better imitation of the real thing than you might expect. We sampled a couple of local beers at The Hog Penny, the oldest pub in Hamilton (opened 1957) whose dingy interiors are very old-school London boozer. (The sunny exteriors, less so.) Pints aren’t cheap – nothing in Bermuda is cheap – but just about sneak under £10. Imagine you’re in Shoreditch with better weather.
We stayed at the Azura, a stylish hotel with a private beach barely a minute from the rooms. Every day started with an ocean swim and a stroll along pristine sands. There must be half a dozen various pools should for some reason you not fancy the real thing. The seafood pasta at the hotel's restaurant Surf can also be recommended.
Azura Hotel
While on the island, a fish sandwich is a must. In Bermuda it's made with raisin bread, a sweet touch that works brilliantly – Mamma Mia cafe and Lido cafe served the two best I tried. For more upmarket dining, Island Brasserie at the Rosewood and at Blu at Belmont Hills both hit the spot; the former is an elegant steakhouse, the latter an extravagant bar and grill serving dishes across multiple cuisines.
Oh god and I haven't even mentioned the Bacchanal Run, the Soca music street party that follows every Cup match. Hundreds of people dance around the streets of Hamilton throwing powdered paint on each other. There's music lorries, booze lorries, glow sticks, live flame and very little clothing. It's bonkers, it's brilliant. It's Bermuda.
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Rooms start from $695 a night at Azura; daily flights from Heathrow start from £884 return
