Where the Pavement Ends Double Loop

SEP
20
2026
Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.
Sun 20 Sep 2026
8 miles 4 miles

Always double-check with the organizer's website! This page may contain affiliate links.

Where the Pavement Ends Single & Double Loop

Where the Pavement Ends Trail Races take place in Ridgefield, CT, at the Lake Windwing ballfields. The course runs through the Hemlock Hills and Pine Mountain open space areas and is described as technical and rocky. The start and finish are located at the Lake Windwing ballfields.

Course options include:

  • Single loop: about 4.25 miles
  • Double loop: about 8 miles, two loops of the same course

Organizers recommend the shorter loop for runners without trail experience. The event is part of the Westchester-Fairfield Trail Mix Series, a set of seven trail races where results from each race are combined to determine a series winner and award special prizes.

Registration opens 12/31/2025 and closes 4/6/2026. Registration fees listed are $42.00 for the single loop and $50.00 for the double loop. The description provided by the organizer notes the course surface is rocky and technical and specifies the general area and venue for the event. Visit the organization's website for the most recent information.

8 mi
Where the Pavement Events - the Double (two Loops)
4 mi
Where the Pavement Ends - Single Loop

Events nearby

Trail race at Great Hollow Lake on October 3, 2026 with timed 5K and 12K races plus a Kids Fun Run and virtual options benefiting a local scholarship and foundation.
A 5K trail run and an accessible short run/walk on private Gemstone Farm in Wilton, CT on 10/10/2026, with farm access, post-event food and entertainment, supporting The Prospector.
Scenic 5K at Rockefeller State Park Preserve featuring hilly carriage roads, age group and team awards, t shirts and refreshments, with proceeds supporting carriage road maintenance.
Trail event at Muscoot Farm in Katonah on October 25, 2026 featuring a 5 mile race and two kids races, with Farm Bucks and kids medals.
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