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Where the Pavement Ends Trail Race

Sep 20, 2026 at 7:00 AM

South Shore Drive/Lake Windwing , Ridgefield CT, 06877, USA

Experience a challenging and fun 4.25 mile trail race that starts and finishes at Lake Windwing. Enjoy this technical, winding course through Ridgefield’s Hemlock Hills. Where the Pavement Ends is part of the Trail Mix Series. This race benefits the Ridgefield Open Space Conservation Fund; this fund is what originally enabled the Town of Ridgefield to purchase Hemlock Hills/Pine Mountain for public use!

Why run this race? It’s not your ordinary trail race. Yes, it’s “only” 4.25 miles, but it’s a rocky, rooty, twisty, climby grand old time! Not to mention the on-course live bluegrass music to keep you moving, and free race photos to humble-brag to your friends. And what other race gives the overall and age-group winners goodies from The Cake Box?!

Where the Pavement Ends Trail Races are set for Sunday, September 14, 2025

Double loop begins at 7:00 AM   Single loop begins at 7:30 AM

                          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.

Event History

2026
Sep 20, 2026
2025
Sep 14, 2025
2024
Sep 08, 2024
2023
Sep 10, 2023
2022
Sep 11, 2022
2021
Sep 12, 2021
2020
Sep 13, 2020
2019
Sep 22, 2019
2018
Sep 16, 2018View Results →
2017
Sep 17, 2017View Results →
2016
Sep 18, 2016View Results →
2015
Sep 13, 2015
2014
Sep 14, 2014
2013
Sep 15, 2013
2012
Sep 23, 2012

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