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Out and about: Cup Match playbook

Have a go: Crown and Anchor is one of the most recognisable traditions of Cup Match (Photograph by Akil Simmons)

By the time Cup Match arrives, Bermuda has already been counting down for weeks. Outfits have been planned, camps have been organised, boats have been booked and family group chats have been buzzing.

And while the game remains at the heart of the holiday, Cup Match has evolved into so much more than a sporting event. It's four days of traditions, food, music and catching up with the people you haven't seen in months.

Whether you're a Cup Match veteran or looking to experience more of the weekend this year, here's how to do it right.

Pick your Cup Match personality

Before the first ball is bowled, most people have already decided what kind of Cup Match they're having. Some won't leave Somerset Cricket Club until the sun sets. Others spend both days camp-hopping between friends and family.

Plenty head straight to the beach, while others make the most of the long weekend on a boat. There's no wrong way to spend Cup Match. Just make a plan and be open to some unplanned magic over the weekend.

Spend some time at the game

Even if you don't know an lbw from a six, the game is still worth experiencing.

Grab a programme, find a seat in the stands (or in someone’s camp) and soak up one of Bermuda's oldest traditions. Take a walk around the club, catch up with friends you haven't seen since last Cup Match and enjoy the atmosphere that makes this weekend unlike any other on the island.

And if you're supporting Somerset or St George's, don't forget to wear your colours proudly.

Make the rounds at the various camping spots

Some of the best moments happen as you make your way from one gathering to the next, catching up with relatives, neighbours and old friends along the way. Expect plenty of music, laughter, swimming, drinks, storytelling and someone insisting you have “just one more plate” before you leave.

Escape to the beach

For plenty of families, the game isn't the main event. Cup Match has long been one of Bermuda's biggest beach weekends, with Horseshoe Bay, Clearwater, Tobacco Bay, Warwick Long Bay and John Smith's Bay filling with families from early morning.

Bring a cooler, plenty of shade, beach games and enough food to keep everyone going until sunset.

Get out on the water

If you have access to a boat, Cup Match is one of the best weekends of the year to use it.

Whether you're rafting up with friends, anchoring in a quiet cove or spending the afternoon fishing, there's nothing quite like seeing Bermuda from the water during the holiday weekend. Just remember to plan ahead, stay hydrated and always designate a sober skipper.

Eat like it's Cup Match

No one should leave Cup Match hungry. This is the weekend to indulge in the dishes that have become synonymous with the holiday. Fish chowder, fried fish, fried shrimp, mussels, barbecue, burgers hot off the grill and homemade family favourites all make an appearance.

And, of course, no Cup Match weekend is complete without at least one snowball and an icy Rum Swizzle.

Try your luck at Crown and Anchor

Whether you're a seasoned player or trying it for the first time, Crown and Anchor remains one of Cup Match's most recognisable traditions.

Even if you're only playing for a few dollars, it's worth joining a game at least once during the weekend. Chances are someone nearby will happily explain the rules if you've never played before.

Dress for the occasion

Cup Match has always been one of Bermuda's biggest fashion weekends. Lightweight fabrics, comfortable footwear and plenty of island style are key, whether you're heading to the cricket, visiting camps or spending the day outdoors.

And yes, expect to see plenty of Somerset red and blue and St George's blue and light blue throughout the weekend.

Start the weekend with live music

The celebrations begin well before the first day of cricket.

This year's entertainment calendar includes major concerts featuring Mavado tomorrow (Saturday) night and both Kes the Band and Wayne Wonder on Wednesday night, giving music lovers the perfect excuse to kick off Cup Match week before the holiday officially begins.

Then, once Friday's play wraps up, Cup Match Fever keeps the energy going with one of the weekend's biggest nightlife events.

Finish strong

By Saturday, the cricket may be over, but the celebrations certainly aren't.

Bacchanal Run has become one of the signature events of Cup Match weekend, bringing thousands of people together for an evening of soca music, energy and one final chance to celebrate before life returns to normal.

Bacchanal Run has become one of the signature events of Cup Match weekend, bringing thousands of people together for an evening of soca music, energy and one final chance to celebrate before life returns to normal (Photograph supplied)

And then, we get to the cool down: Non-Mariners, the unofficial wind-down to the long weekend, giving everyone one last opportunity to catch up with friends, swap stories from the previous few days and enjoy the final hours of Bermuda's biggest holiday before Monday morning arrives.

No matter how you decide to spend the Cup Match holiday, have fun, be safe and don’t drink and drive.

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Published July 24, 2026 at 6:59 am (Updated July 24, 2026 at 7:38 am)

Out and about: Cup Match playbook

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