Cup Match season is officially heating up, and the community is invited to start the celebration early at the Somerset Pre Cup Match Explosion, happening on Friday, July 10, 2026, from 5:00 PM to 9:00 PM at Willowbank Resort in Somerset.
The event is spearheaded by Von-Rica Dickenson, artist, educator, and founder of Community Restoration Group (CRG) and VonJe’ Enterprise, together with lead sponsor Kennette J. Burgess of FOCUS Marketing and Development Solutions Inc. and chief designer of Distinct Apparel.
Created as a community-centered celebration, the Somerset Pre Cup Match Explosion brings together culture, creativity, local business, entertainment, food, fashion, and the friendly team rivalry that makes Cup Match season so special.
And the best part? Entry is completely FREE.
Locals, visitors, families, and Cup Match lovers of all kinds are invited to come out and enjoy an evening at the beautiful Willowbank Resort, where guests can take in the scenic views, enjoy indoor and outdoor vendors, support local businesses, and spend a Friday evening filled with good food, good music, and good company.
Of course, it would not be Cup Match without a little friendly rivalry. Guests are encouraged to come dressed in their team colors and represent Team Somerset or Team St. George’s as the event looks to see which side can bring out the most supporters. Whether you are loyal to one team, still deciding, or just showing up for the vibes, everyone is welcome. After all, Cup Match is serious business—but only until the food, music, and fun start.
Food will also be a major part of the celebration. Willowbank will feature an outdoor grilling food area, with Friday’s menu from Breezeway including jerk chicken, Bermuda corn on the cob, fish on a bun, and Willow Fries to mention a few. The Ocean Café will also be open, serving specialty coffee, sweet treats, and beverages, including alcoholic, non-alcoholic, and frozen options.
Guests can also look forward to a lively fashion show featuring Distinct Apparel, designed by Bermudian entrepreneur and designer Kennette J. Burgess, along with other participating vendor apparel brands and retailers. The fashion segment will showcase a variety of Cup Match-inspired looks that celebrate Bermuda’s culture, Emancipation story, team pride, and the fun personalities that come with the season. From loyal team supporters to all-team fans, bandwagonners and even the proud “I’m just here for the vibes” crowd, the runway will bring style, culture, local creativity, and a touch of Bermudian humor to the celebration. Because in true Cup Match fashion, it is not only about who you support—it is also about how good you look while supporting them.
Other fashion designers for the fashion show will include Betty’s Collections, Seven Collection, and Tiny Bermuda.
The evening will also feature local entertainment by DJ Coverboy, who will be launching “Atmosphere” during the happy hour segments, along with a live Gombey performance by SMS to bring even more cultural energy to the event. You can’t miss this event, because Bermuda’s international pianist and son stylist, Wayne Davis will be in full effect.
Families are encouraged to attend, with a kiddy corner, bouncy castle, face painting, and other fun activities planned for the whole family. From the little ones to the elders, the event is designed to be a space where everyone can celebrate, connect, and enjoy the Cup Match spirit together.
Attendees will also have the opportunity to shop from local vendors, including but not limited to The Beat the Heat Treats, G W’s New Look Sporting Goods, Candle Sensation, Kairos XX11 Productions, Island Girl Papercrafter, Nii’s Flake Factory, Flo by Nico, Ava Made with Love, Casual Footware, Seven Collection, Blended, Patch That, Just Face It Face Painting, SCARS, Simply Vanilla Delight & Co, and Steady Snackin.
While admission is free, guests are encouraged to bring both cash and credit/debit cards for food, drinks, snacks, shopping, and other purchases throughout the evening.
The Somerset Pre Cup Match Explosion is proudly supported by sponsors including PIM Contracting, New Line Construction, TRS Traditional Rum Swizzle, On All Fronts, Esso Sandys, BEDC and lead sponsors Vonart, Distinct Apparel and FOCUS Marketing and Development Solutions Inc.
The event will also include many exciting giveaways from sponsors and community partners, including Caesar’s Pharmacy, Bargain Hunters, Brother Black’s TRS, Yo Cherry, Side Kicks, Fit & Fierce and more. Willowbank Resort will also be giving away a special day pass with lunch for two persons, adding even more excitement to the evening.
More than just a pre-Cup Match event, the Somerset Pre Cup Match Explosion is a celebration of Bermuda’s community spirit, culture, family, local business, and the joy of coming together before one of the island’s most beloved holidays.
With free entry, beautiful views, food, fashion, entertainment, giveaways, vendors, and activities for all ages, this is one Friday evening locals and visitors will definitely want to be part of.
Event Details:
What: Somerset Pre Cup Match Explosion
When: Friday, July 10, 2026
Time: 5:00 PM – 9:00 PM
Where: Willowbank Resort, Somerset
Admission: Free entry
Fashion Show: Starts at 7:30 PM
All local residents and visitors are invited to attend. Let’s see which CupMatch team will have the most representation!
