Lace up for the Run For The Trees - Jeannette Genius McKean Memorial 5K on May 9, 2026, in scenic Winter Park, FL. This beloved 3.1-mile event, a collaboration between Track Shack and the City of Winter Park, offers a unique point-to-point course that runners consistently praise for its beauty and fast, flat elevation. Participants will wind through picturesque Winter Park neighborhoods before embarking on the race's signature feature: the final mile along the tree-canopied, wilderness dirt road of Genius Drive. This privately owned road opens to the public only once a year for this event, offering an exclusive glimpse of old Florida complete with lush nature, big oaks, Spanish moss, and even peacocks.

The Run For The Trees 5K stands out for its commitment to environmental stewardship, as all in-person finishers receive a young tree sapling to plant, contributing to the Winter Park Tree Replacement Fund. This is a "cupless race," promoting sustainability by providing complimentary HydraPak SPEEDCUPS at registration and offering touchless water stations on the course and in the event area. Starting at Ward Park, the event is walker-friendly with a 15-minute per mile pace limit, and a free Kids' Run is available for younger participants. Typical race day conditions in early May can see highs around 88°F and lows around 68°F, with a 13% chance of precipitation.

Beyond the challenge of the 5K, the atmosphere is vibrant and supportive. Runners will find touchless water stations along the course to stay hydrated. Finishers, in addition to their tree, may also compete for unique awards, as top overall and age group winners receive quality landscape trees with a significant retail value. After crossing the finish line, there's a 1.3-mile walk back to the post-race area, where the overall awards ceremony takes place at the Track Shack tent.