Trail Running calendar near Westfield 2026-2027

Experience the beauty of the Shawangunk Mountains with a 50 mile ultra, a trail marathon, or a team relay. Enjoy well maintained carriage roads and an 18 hour cutoff in this premier fundraising event for Mohonk Preserve.

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.

Experience one of the most technical and elevation dense trail races in the Northeast. Tackle steep climbs and rugged single track through the scenic terrain of Beacon, New York.

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.

Trail races in Lyme, Connecticut offering a 9.2 mile loop and a 3 mile sprint on Mount Archer trails. Chip timed and rain or shine, with 100% of proceeds donated to local emergency services.

A technical trail race on the Wapack Trail in Ashburnham, MA on May 9, 2026, offering 21.5, 43 and 50 mile options over rocky single track and significant elevation. Registration is limited, manually timed, and nonrefundable.

Run for a cause at the Bruynswick Winery Run, a 6k cross-country race benefiting the Ulster County SPCA. Enjoy a scenic course at the foot of the Shawangunk Ridge, with music, drinks, and a chance to meet shelter animals. Free children's da..

Experience the eighth annual Spring Fling 600 trail races at YMCA Camp Sloper. Choose between a 6 mile race or a 10 hour challenge to complete as many loops as possible on a scenic three mile course.

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..

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

Annual May races on the Ashuwillticook Rail Trail offering marathon, half and 8K distances starting and finishing at the Adams Visitors Center. Proceeds support the rail trail and a municipal fund for the City of Pittsfield.

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.

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.

Experience a scenic trail run through the meadows and forests of Muscoot Farm. Choose from the 5 mile course or youth races and receive vouchers to spend at the local farmers market.

Trail races at Soapstone Mountain in Stafford Springs, CT include a new half marathon and the Jerry Stage 6K Sampler. Courses run on the blue blazed Shenipsit Trail through Shenipsit Forest with on course aid for the half marathon.

Run a 3.5-mile trail race in Wolcott, CT. The event supports the local cross country teams. Your entry includes access to the CT Food Truck Battles Festival afterward.

Join this adventure based event in Barrington featuring a 1.5 mile neighborhood loop and an accessible adaptive course. This family focused run includes electronic timing and performance shirts for the first 1,000 participants.

A community campus event in East Haddam featuring a 1.75 mile looped course with rocky dirt paths, kids races on the soccer field, reused-trophy awards, dog-friendly provisions, and water stops on a rain or shine race day.