Cheshire Half Marathon, Relay & 5K

Sunday, October 18, 2020 • Cheshire, CTCourse Map

October weather may still be cool in Connecticut, but that’s the perfect time to start (or finish) your running season, and the Cheshire Half Marathon provides a fun race to jump-start anyone’s race season.

The half marathon begins and finishes at Cheshire High School, south of downtown Cheshire. From there, the course heads out of the high school and west onto Higgins Road before making a loop through a residential area to the west of the start line, then turning left onto the Farmington Canal Heritage Trail.

The course continues along the trail for four miles before making a sharp right turn onto River Road and continuing north along Brooksvale Avenue, Mt. Sanford Road, and Brooksvale Road. After a brief second stint on the Heritage Trail, half marathoners retrace most of their steps from the first mile of the course before crossing the finish line on the Cheshire High School track.

For runners not ready to take on the full half marathon alone, a 5K course is available, along with a 2-person relay of the half marathon.

Race Weather & Climate

Located in the northeastern United States known for its cold winters, Cheshire experiences cool fall weather that can get cold, especially in the mornings. Precipitation for the month of October is almost 5 inches on average.

On race day (Oct. 18), the average low is 40ºF and the average high is 63ºF.

Past Results

Course Map

See the race route map for the Cheshire Half Marathon here.

Starting Time

  • 7:45 AM – kids fun run
  • 8:30 AM – half marathon, relay
  • 8:36 AM – 5K


see race website


To reserve your spot in the 2020 running of the Cheshire Half Marathon or 5K race, register online at here.

Official Race Website

Facebook Conversations

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See more races in: October, Connecticut