Where the Pavement Ends Single & Double Loop

Where the Pavement Ends Trail Races are set for Sunday, September 20, 2026 You can do one loop of the course or do two loops for a “Pavement Double”! The race starts and ends at Lake Windwing ballfields in Ridgefield, CT. The 4.25-mile course (single loop) begins at 7:30 AM, and the 8-miler (approximate double loop) begins at 7:00 AM. The course runs through the Hemlock Hills/Pine Mountain open space areas. It's technical, rocky, and sublime. If you are not an experienced trail runner, we recommend choosing the 4.25-mile course. This race is part of the Trail Mix Series—Westchester-Fairfield Trail Mix Series: a series of seven trail races. The results from all the races are combined to determine a series winner and award special prizes.