Trail Running calendar near Westfield 2026-2027

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.

Trail races at Monastery Trails in Cumberland, RI on March 14, 2027 offer distances from a 1 mile kids run to a 100K 12 hour ultra. Team ultra entries and a multilap 5 hour option are available and all finishers receive a medal.

A six hour trail ultra at Roosevelt Forest in Stratford, CT on March 20, 2027, offering a 50K option on a 2.3 mile loop of roots, rocks and rolling hills, with a capped field of 50 entrants and on-course food and hydration.

Trail race in Union, CT on the Nipmuck Trail covering about 16 miles through Yale-Myers Forest. Organized by Shenipsit Striders with limited aid stations and parking; proceeds support local trail stewardship.

A point-to-point ultramarathon across Connecticut, Run Across CT 123 covers about 123 miles from East Thompson to Southport with trail and road sections, a 36-hour cutoff, solo and relay options, volunteer-supported aid stations, and finish..

Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT features a 25K loop with 3K+ of vertical and a 50K two-loop option. The course mixes technical singletrack and carriage roads, includes aid stations, and follows a cupless..

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

An obstacle course race in Cumberland, Rhode Island featuring a 3.2 miles course with about 1,000 feet elevation, multiple wave formats including elite and age group competition, multilap sessions, and a 12 hours ultra option.

Trail races at Penwood State Park on April 17, 2027 include a three-loop 50K and a single-loop 17K over rocky, rolling single track and double-track. The event is cupless, has a waitlist, and is organized by the CT Trailmixers.

A women-centered trail event at Lake Mohegan offering 5K, 10K, and a 4-hour loop on a 3.2 mile trail. The race is open to non-binary runners, follows a cupless aid policy, and includes finisher medals and post-race refreshments.

The TARC Spring Classic takes place April 24, 2027 in Jericho Town Forest, Weston, MA, with 10K, half marathon, marathon and 50K looped trail options, a single aid station, marked course, and a cupless race format.

A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.

Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.

A trail running event on the Wapack Trail in Ashburnham Massachusetts with 21.5 mile, 43 mile, and 50 mile options across rocky, technical terrain with aid stations, drop bag support, and a manual timing system.

A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.

A looped hill endurance event in Cumberland Rhode Island where participants run or hike as many laps as possible within a 12 hour period. The top male and female who cover the greatest distance are named King and Queen of the Hill.

A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.

The inaugural F.I.T. 50k in Cumberland, Rhode Island is a 50k trail ultramarathon with equal parts smooth non technical and moderately technical terrain. The event includes a generous cutoff time and a $65 registration fee.

Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being rebuilt. Proceeds support the Friends of the Fire Tower and park accessibility project..

An iterated loop endurance race in West Greenwich RI where runners repeat a 3.8 mile loop with 450 ft of climb and must complete each loop within 60 minutes until only one runner remains ready to continue.