Trail Running calendar near West Windsor 2026-2027

A 50K at Saskadena Six in South Pomfret VT featuring about 27 miles of hilly dirt roads, 3,726 feet of elevation gain, two full aid stations and an 8 hour cutoff; the 2026 race returns after a two year hiatus.

Prospect Acres 8 hour ultra on April 18, 2026 features repeated 2 mile loops through fields and woods with 230 ft of elevation gain per lap. Free parking, sauna and cold plunges are available and registration costs $25.

A spring trail race at Grafton Lakes State Park covering about 9.3 miles with roughly 900 feet of elevation gain. Trails are technical yet runnable and the course can be muddy in spring.

Celebrate spring in the Adirondacks with a scenic half marathon or a family friendly 5k trail race. Support local healthcare while following a historic route from Keene Valley to Elizabethtown.

The Mucker offers a choice of trail adventures in Hubbard Park, from a 5k hike or ruck to a 5k or 5-mile run. It's part of the Montpelier Mudfest weekend. A kids' obstacle course event runs concurrently on the State House lawn.

On May 2-3, 2026 White Lake Ultras run at White Lake State Park in Tamworth NH. Runners complete a slightly technical 2 mile single track loop with a short beach section and choose from 24 hour, 12 hour, or 6 hour formats.

A 12 mile technical out and back trail race on the Holyoke Range near Amherst, MA, with more than 3,500 ft of elevation gain. Rocky singletrack ridgelines, two manned water stations, and registration currently shows full with a waitlist.

A memorial trail run at Catamount Outdoor Family Center in Williston, VT on May 2, 2026, with a 3-mile in-person race and a weekend virtual option; the event is free and donations to a memorial fund are encouraged.

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.

This 6-mile mountain race tackles steep trails and muddy terrain at Cochran's Ski Area. After the run, enjoy pancakes and watch the free kids' race. It's the opener for the USATF-New England Mountain Running Series.

Experience the original Spartan Trail Race through the steep climbs and winding trails of the Green Mountain National Forest. Choose from distances between 10 and 200 miles for a true endurance test in Pittsfield Vermont.

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.

A trail race on Winant Park Trails near downtown Concord with windy singletrack, switchbacks, and nordic type paths. Two distances are offered and proceeds benefit the Ralph Waldo Emerson School for Preschoolers; day of event entry is avail..

Explore the scenic trails of Whitaker Woods in North Conway with a chip timed 5K or a one mile fun run. This community event supports local health services while offering a mix of flat loops and gradual wooded climbs.

Join the community at the Pinkerton Academy 5K Astro Run in Derry New Hampshire for a scenic 5 km race held on the academy campus grounds.

A 5K trail run in Hanover New Hampshire held on Mother’s Day, featuring packed trails, open fields and mellow single track. Pre registration is online only and race day registration is available with different fees by age group.

Join this weekly trail running series at the Catamount Outdoor Family Center featuring distances from 5k to 10k. There are special categories for children and water stations available on site for all runners.

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.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

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.