Trail Running calendar near Rupert 2026-2027

Sep 19-20, 2026 in Killington, VT: Spartan obstacle races across steep, off-trail terrain in the Green Mountains. Events include Sprint 5 km, Beast 21 km, Ultra 50 km and kids races; tickets start from $29.

Trail run and walk at Huyck Preserve in Rensselaerville NY on Saturday September 19 2026. Routes of 2 5 and 8 miles pass Lake Myosotis and a historic racetrack while raising funds for local organizations.

A community 5K in Jaffrey, New Hampshire on September 19, 2026, offering two course options: a mixed woods trail and a straight rail trail. Proceeds benefit the Jaffrey Firefighters Company Inc.

The Mountain Goat Cabin Trail Run will take place in Rupert on Saturday 19 September 2026. You can run 9 miles.

TAM Trek in Middlebury, Vermont features a full 19 mile loop plus a 10K, 5K and a 2 mile family fun run on trails around Wright Park and Otter Creek.

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 weekend of endurance mountain biking and trail ultrarunning at Ascutney Outdoors in West Windsor Vermont, offering 50 mile and 50 km solo races, multiple relay formats, and kids fun races. Proceeds support Vermont Adaptive.

A community 5K on September 27, 2026 in Dolgeville along the Greenway Trail. Registration has a $25 fee with children under 12 free; proceeds fund free sports equipment for local youth.

The Paine Mountain Anchor Challenge Trail Race will take place in Northfield on Sunday 27 September 2026. You can run between 6 and 8 miles.

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 event in Cohoes, NY offering 1, 3 and 6 hour solo options plus 3 and 6 person relays, organized to raise awareness and funds for Flutters of Hope Inc.

A 50 kilometer trail ultramarathon on October 3, 2026, near Kattskill Bay, NY, covering four Lake George peaks with about 9,000 feet of climbing. The course starts and finishes at Camp Chingachgook and includes multiple aid stations with ti..

Experience the seasonal scenery of New Hampshire at the Keene Family YMCA Fall Foliage Trail Race. Choose between a fast 5K or a 10K with elevation gain to support local community programs.

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.

A trail ultra on Wright's Mountain in Bradford, Vermont on October 10-11, 2026 offering 30 hour, 12 hour and a 10K loop. The course mixes runnable sections with steep, rocky climbs and includes themed tarot card and milestone awards.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

A late-October trail race at Mt. Tom State Park with solo and two person relay options on rugged single-track courses, multiple distances, regular aid stations, significant elevation, and proceeds supporting land conservation.

A trail race in Keene, New Hampshire covering 4.9 miles with about 1650 feet of up and down on ski trails and single track. The event benefits the Keene Community Kitchen and includes prize money, age group awards, and raffles.

A roughly 14 miles trail race at Moreau Lake State Park in Gansevoort, NY, featuring technical singletrack and about 2700 feet of climb with one aid station near six miles; early registrations by October 18 guarantee a shirt.

A backyard ultra at Kenty’s Farm in Winchendon MA on November 7, 2026 where runners repeat 4.1666 mile laps until one remains. The event also offers 6, 12 and 24 hour timed options plus a single lap competition.