Trail Running calendar near Chester 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..

An 8.5 mile trail loop at Merck Forest in Rupert, Vermont with about 1,800 ft of climbing, two aid stations, and a separate 0.75 mile kids loop. Field limits apply and all proceeds support Merck Forest & Farmland Center.

Muddy Princess Boston is a women-focused 5K obstacle mud run at Kimball Farm in Haverhill, MA on June 21, 2026. The event features muddy obstacles, hydration and rinse stations, participant items and a partnership with the National Breast C..

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.

A trail-based 5K obstacle course at Wasserman Park on September 26, 2026, featuring 12+ beginner to intermediate obstacles. Entry is limited to 200 participants, costs $40, and early registrants receive a race shirt and finisher medal.

A trail event at Ascutney Outdoors offering 50 mile and 50K ultra runs, team relays, mountain bike races and kids fun races. Proceeds support Vermont Adaptive and registration details are published for the 2026 race weekend.

A community run at Shedd Park in Lowell offering a 5K, a 10K trail run, and a 1 mile kids loop, with trails, on-course support, family activities, and proceeds benefiting local conservation and education programs.

Trail races in Northfield, Vermont centered at the Norwich Shaw Outdoor Center, featuring a 7.5 mile summit race, an Anchor Challenge 6k, and free youth races. The event raises funds for the Northfield Town Forest and the Norwich cross coun..

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.

A timed endurance running event in Cohoes, NY on October 3, 2026 offering 6 hour, 3 hour and 1 hour options plus relays. It benefits Flutters of Hope, a nonprofit supporting people and families affected by eating disorders.

A 50 kilometer trail race on October 3, 2026 in Kattskill Bay NY that crosses four peaks around Lake George with about 9,000 feet of climb, staffed aid stations, and a registration requirement for prior ultra-trail experience.

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.

Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.

A one-mile community event in Gilford, New Hampshire on October 4, 2026, with categories for adults, youth, and children and a complimentary shirt for those who register before September 16.