Trail Running calendar near Medfield 2026-2027

We have found 75 Trailruns within 80 miles of Medfield. See below where and when you can find the races.

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.

The 5K Race to the Ledges will take place in Concord on Saturday 8 August 2026. You can run 5 kilometers.

Run trails on a 5 km loop for 8 hours at Crandall's Park. It's a potluck celebration with food, raffles, and games. Complete loops to earn tickets for prizes and a commemorative gift.

The Watermelon Wobbler is a 5k trail run/walk/hike through scenic conservation land and a working farm. It features a varied off-road course and supports local agriculture. On-site parking is supplemented by a satellite lot nearby.

The Old Goat Track Club XC Classic is a 5k cross-country race at Waters Farm in Sutton. It features separate men's and women's races and is the opening event for the USATF New England XC Grand Prix. Enjoy a team tent area, awards, and a pos..

September 2026

The Run for the Hills - Niantic will take place in Waterford on Saturday 5 September 2026. You can run 5 kilometers.

The TARC Fall Classic will take place in Carlisle on Saturday 5 September 2026. You can run between 10 and 50 miles.

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Saturday 5 September 2026. You can run 5 kilometers.

Join the Charlie Stavros Memorial Beach Run on September 15, 2026 in Westerly, Rhode Island, a free 3 mile beach run honoring a beloved local runner. Enjoy a scenic low tide out and back along Westerly Town Beach with friends and family.

The Mt. A Trail Challenge is a timed trail run on Mount Agamenticus. Choose from a 5K or 1-mile course, with timing handled by the local high school cross country team. The event raises funds for the mountain's conservation and offers a spe..

A trail race in Hooksett on September 19, 2026, featuring a 5k on stone dust and wooded conservation trails and a half mile kids run for ages 12 and under. Proceeds support Hooksett Kiwanis community and youth programs.

This 5K trail run takes participants through the scenic trails and grasslands of Goddard Park in Warwick. The flat course is open to all ages and abilities. Registration includes a T-shirt and ample parking is available.

Experience a 100% trail run on the newly restored Moosup Valley State Park Trail. Choose between a 10K or 5K race, with a free Kids Fun Run also offered. Your participation supports local community initiatives through the Rotary Club.

October 2026

The Run for the Pumpkins Trail Run will take place in Westerly on Saturday 3 October 2026. You can run between 5 and 10 kilometers.

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..

A 26.4 mile trail marathon in Ashford, CT with a two runner relay option, varied trail terrain and defined course cutoffs including an 8 hour finish limit.

Enjoy autumn trails at the Keene Family YMCA Fall Foliage Trail Races on October 4, 2026, with 5K and 10K options around scenic Keene, NH. Run for community impact while enjoying chip timed courses and seasonal views.

Point to point UTMB Index ultratrail across central Massachusetts with 100 mile, 50 mile and 50 kilometer options, wave starts, and seeded pacing to coordinate aid station support.

UTMB Index

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..