4th Annual Sail to the Finish 2M Run

Sat, May 2, 2026, 1:00 PM EDT

Location: Middlebury, CT; 30 West Lake Road, 06762
Featured distance: 2 Miles
Type: RUN

Vibe analysis coming soon

Course feel, difficulty, and community fit are being added to this listing. Check back, and always confirm details on the official registration page.

At a glance

Perks & features

Dog-Friendly

From the public listing — confirm on the official site.

Auto-drafted from the public listing — confirm details on the official event page before signing up.

Vibe Check

Easygoing

Partial data — terrain or weather signals missing.

The course

From the organizer

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.

Also in this area

More demanding options nearby

Higher-difficulty races in the same state.