Where the Pavement Ends Single & Double Loop 2026 — Ridgefield, CT

Date
September 20, 2026
Location
Ridgefield, CT
Venue
South Shore Drive/Lake Windwing
Start Time
7:00 AM
Entry Fee
$42.00 – $65.00
Events
Where the Pavement Ends - Single Loop, Where the Pavement Events - The Double (two loops)
Includes
Shirt
Register NowRegistration Open
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.

Hotels Near This Race

Find accommodation close to the start line in Ridgefield, CT. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.

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Where the Pavement Ends Single & Double Loop 2026 — Ridgefield, CT

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Race Travel Insurance

Don't forget travel insurance for September 20.

You've trained for months and booked a trip to Ridgefield, CT. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.

  • Trip cancellation up to 100% of prepaid costs
  • Running events covered under standard plans — no add-ons needed
  • Trip interruption up to 150% of non-refundable costs
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support
Get a Quote — Faye Travel Insurance

Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.

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