Holiday Five

The Holiday Five offers a unique endurance sport challenge at Cady Way Trail in Winter Park, FL. Designed as an intimate and low-key event, it spans five days with courses that are guaranteed not short. Participants enjoy the benefit of low entry fees and a generous time limit but should set expectations accordingly. There are no alluring extras such as shirts, awards, or a finish line party. Assistance includes basic support and light refreshments at aid stations, along with convenient parking. The trail, shared with the public, features repeated loops and street crossings, demanding alertness and self-reliance from participants.