4th Annual Sail to the Finish 2M Run – Middlebury, CT 2026

Date
May 2, 2026
Location
Middlebury, CT
Venue
30 West Lake Road
Start Time
1:00 PM
Entry Fee
$30.00
Events
2M
Register NowRegistration Open
The race is to benefit the Quassapaug Sailing Center, a nonprofit organization designed to provide sailing instruction and encourage and promote good fellowship between persons actively interested in sailing and water sports. Sails to trails summer camp is operated every summer to encourage sailing and outdoor activities for children. Scholarships are offered for children in need. Race is an out and back road course starting at the Quassapaug Sailing Center. First mile is downhill, then you run back up the hill (no complaining- it’s not that steep!). No Dogs allowed! Parking is limited - carpooling is encouraged. Race entries will be limited due to space limitations (likely that the race will sell out- sign up early!). Awards: Overall Male and female finishers & top three in age groups 19 & under, 20-29, 30-39, 40-49, 50-59, 60-69 & 70 & up. Race day is international Harry Potter day - come with your best costume and try to win an award.

Hotels Near This Race

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

RaceHotelFinder earns a small commission when you book through links on this page, at no extra cost to you. Results are sorted by distance from the race venue.

4th Annual Sail to the Finish 2M Run – Middlebury, CT 2026

Race day is approaching. Hotels fill up fast.

--Days
:
--Hours
:
--Mins
:
--Secs
Book a hotel for race weekend

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 May 2.

You've trained for months and booked a trip to Middlebury, 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.

More Races

Browse all upcoming races in Connecticut →

Other upcoming races in Connecticut

17th Annual Barkhamsted River Run 5K 2026 — Barkhamsted, CTBarkhamsted, CTMay 31, 2026From $$10.00
Find Hotels →
Glastonbury Education Foundation 5K Run/Walk (GEF5K) 2026 — Glastonbury, CTGlastonbury, CTMay 31, 2026From $$40.00
Find Hotels →
Run the Vineyards – Jonathan Edwards 5K 2026 — North Stonington, CTNorth Stonington, CTMay 31, 2026From $$44.00
Find Hotels →
TriRidgefield Sprint Triathlon and Duathlon 2026 — Ridgefield, CTRidgefield, CTMay 31, 2026From $$95.00
Find Hotels →

Frequently Asked Questions

When is 4th Annual Sail to the Finish 2M Run – Middlebury, CT 2026?

4th Annual Sail to the Finish 2M Run – Middlebury, CT 2026 takes place on May 2, 2026. The race is held in Middlebury, Connecticut.

Where is 4th Annual Sail to the Finish 2M Run – Middlebury, CT 2026 held?

4th Annual Sail to the Finish 2M Run – Middlebury, CT 2026 is held at 30 West Lake Road in Middlebury, Connecticut.

Where can I find hotels near 4th Annual Sail to the Finish 2M Run – Middlebury, CT 2026?

RaceHotelFinder shows hotels sorted by distance from the race venue in Middlebury. Use the map or list view on this page to compare options and book race weekend accommodation.