Trail Running calendar near Springfield 2026-2027

A community 5K run and a children’s 1 mile fun run at Schodack Town Park on September 19, 2026, raising funds for Hope House. Entry fees include 5K $30 and children free with parents running $30.

TAM Trek is a trail race and fun run in Middlebury, Vermont supporting the Trail Around Middlebury. Events range from a full 19 mile route around the village to shorter trail races and a family friendly two mile run.

A 5K trail race at Loon Mountain on September 20, 2026, as part of the 51st NH Highland Games, with 800 ft of elevation gain across dirt trails, service roads and ski trails. Registration includes a race shirt and festival admission.

A community 5K in Hillsborough, NH on September 20, 2026, organized by the Hillsboro Fire Department. The off-road course may be uneven and strollers are not recommended; registration runs March 25 to September 19 with a $30 fee.

A one lap up and down mountain race in Waterville Valley, New Hampshire on September 20, 2026, part of the USATF-New England Mountain Racing Circuit. The course uses grassy ski slopes and gravel service roads and includes three aid stations..

A fall trail race at Merck Forest and Farmland Center featuring an approximately 8.5 mile loop with about 1,800 feet of climbing and two aid stations. A separate 0.75 mile kids loop circles the farm and allows parent participation.

A women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026. The course has 18+ obstacles, welcomes participants ages seven and up, and emphasizes teamwork over competition.

A timed charity tower climb at Empire State Plaza in Albany that reaches the 42nd floor with 809 steps. Water stations, bailout floors and medics are provided; registered participants receive a t shirt and finisher's medal.

A multisport festival at Pawtuckaway State Park offering swim, bike and run options for people who identify as women. Choose an individual triathlon, two sport combo, single sport or a relay team in a non competitive setting.

Trail based 5K obstacle race at Wasserman Park on September 26, 2026 featuring 12 or more beginner and intermediate obstacles and limited to 200 participants.

Mountain bike and ultra-run event at Ascutney Outdoors near West Windsor VT with 50 mile and 50K options, relays and kids races, benefits Vermont Adaptive.

Trail 10K, 5K run/walk and a kids 1 mile fun run at Shedd Park in Lowell supporting local conservation and education.

Trail races on Paine Mountain near Northfield VT featuring a 7 mile plus summit race, a 6k Anchor Challenge with a 4 person team option, youth races and awards.

Experience a rugged trail race through the Adirondack forests and wetlands of Amy’s Park. Enjoy scenic views and a community after party at a local brewery while supporting land conservation for Lake George.

Timed endurance event in Cohoes, NY on Oct 3, 2026 with 1 hour, 3 hour and 6 hour solo and relay options supporting Flutters of Hope.

A 50K trail race on October 3, 2026 in Kattskill Bay, NY, featuring four peak crossings and about 9,000 feet of climbing.

Trail races in Groton, Massachusetts on October 4, 2026, organized by local running and trails groups. Two distances, 9.5 miles and 3.4 miles, total entries limited to 250, online registration closes October 3.

Keene Family YMCA Fall Foliage Trail Races feature 5K and 10K trail courses starting and finishing at the Keene YMCA, with chip timing, age-group prizes, and proceeds supporting YMCA programs and access.

Trail running at Tibbetts Field in Madbury includes a 5K and a 1 mile fun run over natural terrain through Powder Major Forest, with proceeds supporting youth recreation scholarships.

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.