Trail Running calendar near Wilbraham 2026-2027

A 12 mile out and back trail race on the Holyoke Range in Amherst, MA with more than 3,500 ft of elevation gain on technical singletrack. Runners must carry their own water and two manned stations are provided.

Trail event at Greig Farm in Red Hook, NY featuring 5K and 10K trail runs plus a 5K walk through meadows, orchards, and forest, with cash prizes for the top three overall male and female finishers in the 5K and 10K.

Celebrate National Truffle Day with a chocolate themed trail run at Giddings Park. This event features a three loop 5K for all ages and a kids fun run to support Franklin Elementary School programs.

A technical out and back 50K on New Haven blue trails with about 6,350 feet of climbing, strict time cutoffs, no crews or pacers, and multiple aid stations including water only stops.

Experience a trail run or walk through the campus of The Hartsbrook School in Hadley. Choose between a 5k or a 1 mile race on natural terrain while supporting local land stewardship and agricultural education programs.

A two-race trail event in Lyme CT on May 3 2026 with a 9.2 mile Moore Trail loop and a 3 mile Sprint, both chip timed. All proceeds support the Lyme Fire Department and the Lyme Ambulance Association.

Multi distance trail races along the Wapack Trail from Mount Watatic to North Pack Mountain. The technical, rocky course has large elevation gain, five aid stations, drop bag service and limited entries.

Trail races at Watuppa Reservation in Fall River on May 9, 2026, featuring grassy fire lanes, winding single track and aid stations each lap. Distances offered are 10K, 30K and 50K.

Spring Fling 600 in Southington, CT on May 9, 2026 features a 600 minute looped trail event and a 6 Mile race at YMCA Camp Sloper. Both events use chip timing and offer finisher medals and awards for top competitors.

A community 5 km run and walk on May 9, 2026 at Pinkerton Academy in Derry, NH, with a course across campus and nearby cross-country trails. Proceeds support the Pinkerton Fund to benefit students.

A dog friendly 5K and a 2.6 mile walk at Borderland State Park on May 9, 2026 to benefit School on Wheels of Massachusetts. The event features refreshments, pup cups, kids pupsicles and free t shirts for early registrants.

A community event on May 9, 2026 featuring a Family Color Run and a 5K Trail Run at Hamden and New Haven YMCA locations. Registration runs from Feb 20 to May 8 with entry fees of $10 and $30; first 100 pre-registrants receive a Y giveaway.

Test your endurance on a 2.2 mile loop through the scenic Roosevelt Forest. This nine hour ultra event offers a supportive atmosphere for runners aiming to hit personal distance goals on classic New England trails.

A last person standing loop race on Ragged Mountain where runners repeat a roughly 3.11 mile loop and must finish each lap within one hour; entrants are eliminated if they fail to start or finish a lap, continuing until a single finisher re..

A dirt road 50k in Leyden, Massachusetts on May 16, 2026, with 4,200 feet of elevation change and a course that passes through forests, fields, and an 1870s covered bridge. Registration closes May 13 and there is no race-day entry.

A May race day on the Ashuwillticook Rail Trail offering a marathon, half, 8K and kids mile, with race shirts, finisher medals, aid stations, and proceeds supporting trail maintenance.

Tails & Trails State Forest Run in Pittsfield State Park on May 16, 2026 features 50K, 25K and a 5 mile loop of single track, pine forests and mountain bike style trails while supporting local animal rescues.

A 50 mile point to point ultramarathon from Manchester, NH to Mount Monadnock with about 6000+ feet of gain over road, dirt road and trail. GPX only navigation, limited to 125 runners, with aid stations about every 10 miles.

Run or walk a 5k on the Southern New England Trunkline Trail in Franklin. This event supports the development of an abandoned rail bed into a multi use path connecting local communities.

Celebrate the eighth annual Trillium Spring 5K in Canton or participate virtually from anywhere. Join over 500 runners at the brewery to support Girls on the Run Greater Boston with races for adults and children.