Lace up for the 6th Annual Mashashimuet Park Friends and Family 5K, a cherished community event set for Sunday, September 27, 2026, in the picturesque village of Sag Harbor, NY. This popular 5K run/walk offers a fantastic opportunity to experience the charm and history of Sag Harbor while supporting a vital cause. Proceeds from the race directly contribute to the renovation of Mashashimuet Park's historic structures and a newly established scholarship fund, making every step a stride towards preserving local heritage and investing in the future.

The scenic 5K route begins and concludes within the beautiful Mashashimuet Park, guiding participants on a captivating journey through the village. Runners and walkers will traverse historic streets, passing iconic landmarks such as Otter Pond, the Sag Harbor Whaling Museum, the John Jermain Memorial Library, and Pierson High School—sites deeply connected to the benefactress Margaret Olivia Sage. Local musicians stationed along the course provide an uplifting soundtrack, keeping spirits high as you make your way back to the finish line, where refreshments and views of the park's renovated grandstand await. The well-maintained roads ensure a smooth and enjoyable experience for all participants.

Designed for all ages and abilities, the Mashashimuet Park Friends and Family 5K welcomes both runners and walkers, with strollers permitted to encourage a true family outing. Historically, typical race day conditions in late September in Sag Harbor feature pleasant highs around 73°F and comfortable lows near 58°F, with only a 14% chance of precipitation, creating an ideal climate for a morning race. Mashashimuet Park itself offers ample parking and restrooms, ensuring a convenient start and finish to your memorable race day.