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

Where the Pavement Ends Single & Double Loop is a trail running event held in Ridgefield, Connecticut on September 20, 2026, offering 4.3-mile and 8.2-mile distances. The race starts at 7:00 AM from South Shore Drive at Lake Windwing. Entry fees range from $42 to $65 depending on registration timing and distance selection. This event caters to runners looking for a trail experience in the area, with two distance options allowing both shorter and longer training runs or race efforts on the same morning.
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.
Where the Pavement Ends Single & Double Loop 2026 — Ridgefield, CT
Race day is approaching. Hotels fill up fast.
Race weekend dates pre-loaded on Booking.com. RaceHotelFinder may earn a commission at no extra cost to you.
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
Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.
More Races
Browse all upcoming races in Connecticut →
More Trail Running events with hotel options →
Other upcoming races in Connecticut
Frequently Asked Questions
When is Where the Pavement Ends Single & Double Loop 2026 — Ridgefield, CT?
Where the Pavement Ends Single & Double Loop 2026 — Ridgefield, CT takes place on September 20, 2026. The race is held in Ridgefield, Connecticut.
Where is Where the Pavement Ends Single & Double Loop 2026 — Ridgefield, CT held?
Where the Pavement Ends Single & Double Loop 2026 — Ridgefield, CT is held at South Shore Drive/Lake Windwing in Ridgefield, Connecticut.
Where can I find hotels near Where the Pavement Ends Single & Double Loop 2026 — Ridgefield, CT?
RaceHotelFinder shows hotels sorted by distance from the race venue in Ridgefield. Use the map or list view on this page to compare options and book race weekend accommodation.




