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

A forested 5K on August 9, 2026 at Bridgewater Town Park featuring new trails, modest hills, participation gifts, and prizes for top finishers.
Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.
On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are collected.
On 10/10/2026 the Gemstone Sparkle Sprint 5k at Gemstone Farm in Wilton CT features a timed trail 5k, an accessible stroller run, live music, food and access to the farm, with proceeds supporting The Prospector's mission.
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