Trail Running calendar near Jackson 2026-2027

A 50K ultramarathon at Saskadena Six in South Pomfret, VT, featuring about 27 miles of dirt roads, 3,726 feet of climb, variable footing and weather, two main aid stations, a water stop, and an 8-hour cutoff.

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.

The Big A 50K Trail Race is a challenging loop course on Mount Agamenticus with technical, rocky terrain and significant elevation. Participants can choose their distance, from 10 miles up to the full 50K. The event is free to register for,..

A trail half marathon in Gorham, NH on May 3, 2026, starting and finishing at Big Day Brewing. The roughly 13.1 mile route is mostly singletrack with short paved, gravel and woods road sections and significant elevation change.

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..

Trail running festival in Rollinsford, NH offering a 5 Miler, a 5K and a Canicross 5K on mixed rail trail and river single track, with specific rules for canicross teams and an aid station on the 5K route.

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.

Test your endurance at this backyard style ultra race on the coastal trails of Kate Furbish Preserve East. Run 4.17 mile loops every hour through scenic single and double track paths for up to 50 miles total.

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

Community road event in Bethel, ME with an in-person 5K on May 16 and a virtual 5K option May 1 through May 16. It supports after school and enrichment activities for K-12 students in MSAD 44.

Cross country 5K at Cole's Family Farm in Dayton on May 16, 2026 supporting the Southern Maine Young Marines. Options include a 1.25K fun run and a 5K ruck march; entry includes a patriotic t-shirt and participation medal.

Experience Maine's premier trail running festival featuring races from 5K to 100K. This multi day event includes a 30 hour endurance challenge, dog friendly canicross races, and a sunset run at Pineland Farms.

Trail races in Westmore, Vermont on May 30, 2026 include a half marathon, 10 miler and two 5k options over dirt roads and private trails, with a farm to table meal, live music and an evening barn dance.

A 23 km lollipop trail race in the White Mountain National Forest around Mt Chocorua with roughly 4,500 feet of elevation gain, technical rocky trails, mandatory mountain gear, and a 250-runner field.

A trail event on Wrights Mountain in Bradford, Vermont on June 6, 2026, with a 5K summit climb and a 1.5 mile fun run for ages 13 and under. Proceeds support the Friends of Wrights Mountain Fund.

Sunapee Scramble on June 7, 2026 is a 9.2 mile up and down mountain race with 3,250 feet of vertical, serving as the 2026 USATF National Classic Mountain Championship and the selection race for the US Classic Up and Down team.

A 6 mile trail race in Pownal featuring single track paths and rolling hills. Limited to 180 runners, this event kicks off the Bradbury Mountain Trail Race Series with a focus on community and local conservation.

Experience a 6.9 mile mountain race at Cannon Mountain featuring 3,080 feet of elevation gain. Run through technical ski trails and rocky ridges to reach a 4,031 foot summit with views of Franconia Notch State Park.

Experience a unique mountain race alongside the historic Cog Railway to the summit of Mount Washington. Choose between a steep 2.75 mile climb or a technical 5.5 mile round trip through the rugged Presidential Range.

Catamount Ultra in Stowe, Vermont features a 25K loop of wide, hard-packed trail through pastures and hardwood forest and a 50K option covering the loop twice on June 20, 2026.