Lace up for love and community at the Cupid's Chase 5K Key West, set to take place on Saturday, February 14, 2026. This popular 3.1-mile race kicks off at 9:00 AM from the scenic Higgs Beach Pavilion, offering participants a unique Valentine's Day experience in beautiful Key West, Florida. Known for its exceptionally flat course with zero elevation gain, runners will enjoy a swift and enjoyable run along the waterfront, soaking in the picturesque island scenery. Typical race day conditions in mid-February boast comfortable highs around 77F and lows around 65F, with a minimal 8% chance of precipitation, providing ideal running weather.

The Cupid's Chase 5K is more than just a race; it's a celebration of inclusion and support for a worthy cause, benefiting Community Options, Inc., a national non-profit providing housing and employment opportunities for individuals with disabilities. This 18th annual event is fully accessible, welcoming runners, walkers, those with strollers, wheelchairs, and even leashed pets to join the festivities. Participants can show their relationship status by choosing to wear a white shirt if single and ready to mingle, or a red shirt if taken.

Upon crossing the professionally timed finish line, all participants receive a commemorative Cupid's Chase finisher medal and a drawstring bag. Runners who register by January 1, 2026, are guaranteed a race shirt. Trophies are awarded to the top three overall male and female finishers, with age group medals presented across 14 categories. Aid, including water and granola bars, will be available on the course to keep runners refreshed, and a first aid station will be on site. This event promises a fantastic atmosphere and a memorable way to spend Valentine's Day while supporting a great cause.