7th/14th/21st. The Fidelity Fun Run Series will host 2-mile runs on the first three Saturdays in September beginning on Walkers Road opposite the former John Gray High School. caymanactive.com
8th. Every year the Mercuryman plays host to top-class local and international athletes. Competition includes the Half-Iron Distance (1.2-mile swim/56-mile bike/13.1-mile run), International Distance (0.6-mile swim/28-mile bike/6.5-mile run) and Aquabike (1.2-mile swim /56-mile bike) competitions. mercurymantri.com
14th. The Cayman Islands Aquatic Sports Association and Foster’s Food Fair present the 35th Annual Foster’s Food Fair IGA 800m Sea Swim. caymanactive.com
15th/29th. The annual Deputy Governor’s 5k Challenge is raising funds for the Cayman Islands Crisis Centre, the Special Needs Foundation Cayman and the Alex Panton Foundation. Join in on the 15th on Cayman Brac and the 29th on Grand Cayman. facebook.com/DG5KChallenge
26th–28th. The 10th Annual Cayman Islands Healthcare Conference focusing on “Innovating the Future of Healthcare: building on a Decade of Progress” will be held at The Ritz-Carlton, Grand Cayman. healthcareconference.ky
5th. The Cayman Islands Powerlifting Organisation hosts the country’s first Strongman Competition, featuring Eddie “The Beast” Hall. A portion of the proceeds will go to local charities.
6th. Ahoy, mateys! Pirates Week events get off to an early start this year with the annual To Hell and Back 10k race, winding from the Kimpton Seafire Hotel to Calico Jack’s. caymanactive.com
13th. Prep those paws for the Cayman Islands Humane Society’s annual Walk and Wag 5k. Funds raised go directly to helping the dogs and cats at the humane society.
Take your taste buds on a culinary trip to the Greek Isles and the Mediterranean with Anchor & Den’s Argo – Greek Flair + Turkish Bazaar, taking place every Tuesday from
6 p.m. marriottgrandcaymanbeachhouse.com
For a delicious Sunday Brunch with incredible views, head to Ferdinand’s Restaurant at The Westin Grand Cayman. Available each Sunday between 11:30 a.m. and 2:30 p.m., the brunch is hailed as one of the best in Cayman. marriott.com
Hop on a nonstop Cayman Airways flight to Kingston for the city’s 5th annual Jamaica Food & Drink Festival. From October 26th through November 3rd, the island’s most talented chefs, masters and wine and spirit experts serve up good eats, drinks and amazing vibes. jafoodanddrink.com