Explore the Highlands Trail, challenge yourself, and win fun prizes! Anyone can enroll in the Highlands Hiking Challenge. Between April 1st, 2025, and October 31st, 2025, complete as many miles of the Highlands Trail segments as possible. Hit the following mileage benchmarks and receive a patch and certification of completion: 10, 25, 50, or 100+ miles. At the end of the 7-month challenge, the top 3 individuals with the most cumulative miles will also get a 1st, 2nd, and 3rd place prize. Miles can be unique or repetitive. Prizes will be sent after the challenge ends in November 2025. Please abide by the honor system when submitting your mileage; we won’t ask for 3rd party tracking data (like Strava).