Swimming: Cayman’s Jordan Crooks beat Olympic champion Caeleb Dressel in a 50-metre freestyle heat at the University of Virginia, clocking 20.48 seconds as he builds toward the 2028 Olympics. Arts: The National Gallery’s Big Art Auction 9 is underway, with works by leading Cayman artists on display. David Bridgeman’s mixed-media Flying Machine explores memory, identity and distance; the biennial auction raises funds for the Gallery’s development. Music: Grand Old House’s Vinyl Nights bring classic records to a South Sound crowd, with local DJ and sound engineer Buzz Adjusta behind the turntables. The gathering grew from friends listening to records at home into a regular Friday-night event. Culture: Pirates Week 2026 opens in Cayman Brac on 30 October, then moves to Grand Cayman and Little Cayman through 21 November. The 49th festival’s “Spirits, Gold & Glory” programme includes parades, live entertainment, heritage events and family activities.
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Pirates Week: Cayman’s 49th national festival begins in Cayman Brac on 30 October under the theme “Spirits, Gold & Glory,” with parades, fireworks, live entertainment and family events planned across all three islands through 21 November. Community Run: More than 700 people registered for Sunday’s Derek Larner Memorial Run, a record turnout for the event, which raised funds for Jasmine Palliative & Hospice Care and the Cayman Islands Cancer Society. Arts: Stella Maris is marking its 33rd season with new works and Caribbean collaborations. Football: Cayman’s Under-15 team was beaten 7–0 by Trinidad and Tobago at the FIFA U-15 World Cup and Festival in Azerbaijan.
Youth Football: Cayman’s Under-15s were beaten 7-0 by Trinidad and Tobago at the FIFA U-15 World Cup and Festival in Azerbaijan. Community Events: The Central Caribbean Marine Institute brought science into the community with school visits, a free public lecture and its Festival of Seas gala. Island Spotlight: A new travel feature celebrates Rum Point as the birthplace of the Mudslide and a North Side beach-bar favourite. Theatre: Stella Maris marks its 33rd season with new work and Caribbean collaborations.
Youth Football: Cayman’s Under-15s suffered a 7-0 defeat to Trinidad and Tobago at the FIFA festival in Baku. T&T have since advanced to face France. Celebrity News: Savannah Chrisley announced she is expecting her first child and is engaged to Jason, who proposed during a trip to the Cayman Islands. The couple have moved their wedding plans to May 2027. Ocean & Community: The Central Caribbean Marine Institute brought marine science to Grand Cayman with a public workshop, school visits, a lecture and its Festival of Seas fundraiser. Caribbean Dance: Stella Maris Dance Ensemble’s 33rd season featured regional collaborators, including Cayman artists, in works exploring Caribbean identity and heritage. Island Life: A new travel feature spotlights Rum Point as the birthplace of the Mudslide and a favourite Grand Cayman beach stop.
Celebrity News: Savannah Chrisley says she’s expecting her first child and is engaged to Jason, who proposed in the Cayman Islands; their wedding has been postponed until May 2027. Ocean & Community: CCMI is bringing marine science to Grand Cayman with school visits, a free public lecture, a communications workshop and its Festival of Seas gala. Island Events: Pirates Week returns for its 49th year under the theme “Spirits, Gold & Glory.” Food & Leisure: A travel feature spotlights Rum Point as the birthplace of the Mudslide, pairing the famous cocktail with Grand Cayman’s North Sound beach.
Field Hockey: Cayman’s men competed in Florida’s Tampa Cup, testing themselves against U.S. and Caribbean teams in the 7-a-side tournament. Ocean & Arts: CCMI brings marine science into the community this week with a free communications workshop, school visits, a public lecture and its Festival of Seas fundraiser. Football: Cayman’s U-15s fell 7-0 to Trinidad and Tobago at FIFA’s youth festival in Baku. Island Events: Pirates Week returns for its 49th edition under the theme “Spirits, Gold & Glory.” Dance: Jamaica’s Stella Maris Dance Ensemble celebrated its 33rd season with new works and Caribbean collaborations, including Cayman participation, exploring heritage, resilience and identity.
Youth Football: The Cayman Islands Under-15s were beaten 7-0 by Trinidad and Tobago at the FIFA U-15 festival in Baku, Azerbaijan. Grand Cayman Getaway: Rum Point, famed as the birthplace of the Mudslide, pairs the signature cocktail with a North Side beach and waterfront dining. Caribbean Dance: Jamaica’s Stella Maris Dance Ensemble marked its 33rd season with new works and collaborations involving Cayman artists, exploring Caribbean identity and heritage. Pirates Week: The Cayman Islands is preparing for its 49th celebration under the theme “Spirits, Gold & Glory.”
Cayman on Screen: Cayman filmmakers are among 10 countries and territories represented at the BVI’s 284 Excellence Film Festival, opening Oct. 29 with screenings, workshops and industry sessions. Dance & Culture: Jamaica’s Stella Maris Dance Ensemble marked its 33rd season with new and returning works, bringing together artists from Jamaica, Cuba and the Cayman Islands. Youth Football: Cayman’s Under-15s are competing in FIFA’s inaugural eight-a-side festival in Baku; Trinidad and Tobago opened with a 3–1 win over St Kitts and Nevis ahead of a scheduled match against Cayman. Island Traditions: The Cayman Islands is preparing for the 49th Pirates Week under the theme “Spirits, Gold & Glory.” Grand Cayman Flavour: Rum Point Club, widely known as the birthplace of the Mudslide, pairs the signature frozen cocktail with a North Side beach escape.
Youth Football: Trinidad and Tobago opened the FIFA U-15 festival in Baku with a 3–1 win, and the Cayman Islands are among their Group S opponents. Dance: Stella Maris Dance Ensemble’s season closes today in Jamaica, featuring new Caribbean collaborations and works exploring heritage and identity. Pirates Week: The Cayman Islands is gearing up for its 49th Pirates Week, themed “Spirits, Gold & Glory.” Caribbean Film: The BVI’s 284 Excellence Film Festival opens October 29, with Cayman among the territories represented in this year’s submissions.
Caribbean Dance: Stella Maris’s 33rd season, running through October 25 in Jamaica, brings together choreographers and performers from Jamaica, Cuba and the Cayman Islands for new works exploring Caribbean identity and heritage. Film: The BVI’s 284 Excellence Film Festival opens October 29, with Cayman among 10 countries and territories represented in its 30 submissions. The four-day event includes screenings, workshops and industry sessions. Pirates Week: Cayman’s national festival returns October 30–November 21 under the theme “Spirits, Gold & Glory,” with celebrations across all three islands. Youth Football: Cayman’s Under-15 team is among the groups competing in the inaugural eight-a-side FIFA U-15 World Cup and Festival in Azerbaijan, running through October 31.
Youth Football: The Cayman Islands are in Group S for FIFA’s inaugural Under-15 festival in Baku, Azerbaijan, facing teams from Trinidad and Tobago, St. Kitts and Nevis, Egypt, Iraq and Macau. Dance: Stella Maris Dance Ensemble’s 33rd season runs through Oct. 25 at The Little Theatre, featuring new work and Caribbean collaborations, including Cayman performers. Pirates Week: The festival returns Oct. 30–Nov. 21 across all three islands under the theme “Spirits, Gold & Glory.” Caribbean Film: The BVI’s 284 Excellence Film Festival opens Oct. 29 with 30 submissions from 10 countries and territories, including the Cayman Islands, plus screenings, workshops and masterclasses.
Pirates Week: The Cayman Islands has announced “Spirits, Gold & Glory” as the theme for its 49th festival, running across all three islands from October 30 to November 21. Grand Cayman’s events are set for November 6–14. Caribbean Film: The BVI’s 284 Excellence Film Festival opens October 29 with 30 submissions from 10 countries and territories, including the Cayman Islands. The four-day programme features screenings, workshops and industry events. Cayman Karate: Twelve-year-old Gavin Kyrie Rugrug won gold for the Cayman Islands at the Orlando International Karate Open, just months after taking up the sport.
Pirates Week: The Cayman Islands’ 49th national festival will run October 30 to November 21 under the theme “Spirits, Gold & Glory,” with celebrations across Cayman Brac, Grand Cayman and Little Cayman. Caribbean Film: Cayman filmmakers are among 30 submissions from 10 countries and territories selected for the 284 Excellence Film Festival in the BVI, which opens October 29. The four-day event will feature screenings, workshops, industry sessions and an awards celebration.
Youth Swimming: OtisAir has become a platinum sponsor of the Camana Bay Aquatic Club, supporting programmes that serve more than 300 members, from beginners to competitive swimmers. Pirates Week: Cayman’s national festival will run October 30 to November 21 across all three islands, under the theme “Spirits, Gold & Glory.” Caribbean Film: The BVI’s 284 Excellence Film Festival opens October 29 with 30 submissions from 10 countries and territories, including the Cayman Islands; organizers also plan screenings, workshops and filmmaker networking. Cayman Talent: Twelve-year-old Gavin Kyrie won gold for Cayman in novice kata at the Orlando International Karate Open, just months after joining the national training programme. Filmmaker Recognition: The Bahamas International Film Festival is set to honour Bahamian and Caymanian filmmakers.
Caribbean Film: The 284 Excellence Film Festival runs October 29 to November 1 in the BVI, with 30 submissions from 10 territories, including the Cayman Islands. The programme includes screenings, workshops and filmmaker networking. Pirates Week: Cayman’s national festival returns October 30 to November 21 under the theme “Spirits, Gold & Glory,” with celebrations planned across all three islands. Local Arts: Gimistory 2026 is inviting audiences to “An Island of Dreams,” while BIFF will honour Bahamian and Caymanian filmmakers.
Caribbean Film: The 284 Excellence Film Festival returns to the British Virgin Islands on October 29, with 30 films from 10 territories, including the Cayman Islands, plus screenings, workshops and industry events. Cayman Celebrations: Pirates Week runs October 30 to November 21 across all three islands under the theme “Spirits, Gold & Glory.” On the Arts Calendar: Gimistory 2026 is inviting audiences to its “Island of Dreams,” while the Bahamas International Film Festival will honour Bahamian and Caymanian filmmakers.
Pirates Week: Cayman’s biggest national celebration returns Oct. 30–Nov. 21 under the theme “Spirits, Gold & Glory,” with events across all three islands. Caribbean Film: The 284 Excellence Film Festival runs Oct. 29–Nov. 1 in the British Virgin Islands, with Cayman among 10 territories represented in its 30 film submissions. BIFF will also honour Bahamian and Caymanian filmmakers, while Gimistory 2026 invites audiences to an “Island of Dreams.” Cayman in the Spotlight: Swimmer Jordan Crooks set a U.S. Open record in the 50-metre backstroke at a Virginia meet, clocking 22.60 seconds. Young karateka Gavin Kyrie Rugrug won international gold for Cayman after just months of training. Endurance Feat: Cayman resident Kerri Kanuga became the first Canadian woman to finish Greece’s 246-kilometre Spartathlon, crossing the line in 35 hours, 24 minutes.
Pirates Week: Cayman’s biggest national festival returns October 30 to November 21 under the theme “Spirits, Gold & Glory,” with events across all three islands. Cayman Brac opens the celebrations, followed by Grand Cayman and Little Cayman. Swimming: Caymanian Jordan Crooks won the 50-metre freestyle at a Virginia meet in 20.48 seconds, ahead of world champion Caeleb Dressel. He also set a U.S. Open record in the 50-metre backstroke. Bahamian Lamar Taylor broke two national records at the same meet. Cayman Culture: Gimistory brings five nights of storytelling, music and folklore to the islands from November 1 to 6, featuring local performers and international guests. Caribbean Film: The BVI’s 284 Excellence Film Festival received 30 submissions from 10 countries and territories, including the Cayman Islands, for its October 29–November 1 programme. Young Caymanian Talent: Twelve-year-old Gavin Kyrie Rugrug won international karate gold in Florida after less than a year of training in Cayman.
Cayman Sporting Success: Twelve-year-old Gavin Kyrie Rugrug won international karate gold for the Cayman Islands, just nine months after starting training. Swimmer Jordan Crooks also shone at a Virginia meet, setting a U.S. Open record in the 50-metre backstroke and winning the 50 freestyle. Island Stories: Gimistory returns November 1–6 with five free nights of storytelling, music and Caymanian culture, travelling across all three islands. Caribbean Film: The 284 Excellence Film Festival runs October 29–November 1 in the BVI, with Caymanian films among 30 submissions from 10 countries and territories. Endurance Feat: Cayman resident Kerri Kanuga became the first Canadian woman to finish Greece’s 246-kilometre Spartathlon, crossing the line with just over half an hour to spare.
Caymanian Achievement: Cayman resident Kerri Kanuga became the first Canadian woman to finish Greece’s 246-kilometre Spartathlon, completing the race in 35 hours, 24 minutes. She previously ran it representing the Cayman Islands. Caribbean Film: The 284 Excellence Film Festival returns to the British Virgin Islands from October 29 to November 1, with 30 submissions from 10 countries and territories, including the Cayman Islands. The programme features screenings, workshops and industry events. Island Stories: Gimistory returns November 1–6 with five nights of storytelling, music and folklore across the Cayman Islands, from Cayman Brac to Pedro St. James. The free festival features local performers and guests from Jamaica and Ireland. Cayman on the Ice: Cayman Islands-born Jaxon Cover scored a goal and three points as the London Knights beat the Sudbury Wolves 4–1, handing the Wolves their first regulation loss of the season.
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