Trail Running calendar near Princeton 2026-2027

Point-to-point trail races on the Wapack Trail offering 21.5, 43 and 50 mile options over rocky, technical terrain with significant elevation gain; five aid stations, manual timing, drop bag service, and a strict no-refund registration poli..

A trail race on Concord's Winant Park Trails with short (about 3.5 miles) and long (about 7 miles) courses. Proceeds benefit the Ralph Waldo Emerson School for Preschoolers in Concord, NH.

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.

Trail running festival in Rollinsford NH along the Salmon Falls River, featuring a 5 Miler, 5K and Canicross 5K that mix rail trail, open fields and river single track.

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 last person standing event on rugged Ragged Mountain in Berlin CT where runners repeat a roughly 3.11 mile loop each hour until one runner remains. Entry is limited to 55 and proceeds support local trail and youth running programs.

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 5 km cross-country event at Canterbury Shaker Village on May 16, 2026 with in-person and virtual options. Online registration closes May 15 at 12:00 noon ET and the registration fee is $25.

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.

Trail running in Pittsfield State Park with 50K, 25K and a 5 mile course on single track and flowy forest trails. The event is organized by BURCS and benefits local animal rescue organizations.

A 50-mile point to point ultramarathon from Manchester to Mount Monadnock with about 6000 feet of gain over roads, dirt roads and trails. The course is GPX only with minimal markings, five aid stations, and a 125-runner cap.

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.

Wason Pond Wrangler is an obstacle race on May 16, 2026 in Chester, New Hampshire, featuring a 5 km course run in multiple waves including a competitive wave. Online registration is closed and the event is limited to 800 participants.

New for 2026: an all-new Soapstone Mountain Half Marathon and a 6K Sampler in Stafford Springs, CT, both routed through Shenipsit Forest and past the Soapstone fire tower. The event is part of the Blue Blazed Trail Running Series and suppor..

A 25th annual cross country event in Newburyport, MA on May 17, 2026 with adult and youth 3 mile races plus a kids 1/2 mile. First 250 3 mile registrants receive shirts and race day donations support the Travis Landreth Scholarship Fund.

Tough Tiger is an obstacle course event at Hampden Meadows School in Barrington, RI offering a 1.5 mile loop and a shorter adaptive course, with T shirts for early registrants, a raffle, and electronic timing.

A community 5K through the PEA trails in Exeter plus kids fun runs in three age groups, post race music, food, raffles and awards. Free babysitting is provided for children of registered 5K participants.