Trail Running calendar near Plymouth 2025-2026

The Paine Mountain Anchor Challenge Trail Race, held in Northfield, Vermont, is a scenic and challenging 6K trail race that starts and finishes at the Norwich Shaw Outdoor Center. The course features a mix of gravel roads, single-track switchback trails, and steep descents, leading runners to the su..

The Hooksett Kiwanis 5K Trail Race, held in Hooksett, New Hampshire, is a scenic trail run starting at Heads Pond trail and finishing at the Hooksett Public Library. The course features a hard-packed stone dust surface and wooded conservation trails, offering a natural and enjoyable running experien..

ACT Trail Fest is the Arundel Conservation Trust’s 5th annual trail event in Arundel, Maine. On September 20, 2025, participants can choose from a 5k, 10k, or half-marathon along the ACT Multi-Purpose Trail and the Eastern Trails, starting and finishing at the Arundel Municipal Building parking lot..

Bear Brook Trail Races take place at Bear Brook State Park in Allenstown, New Hampshire. The event offers three trail races: Marathon, Half Marathon, and 10K (the 10K follows Mindy’s Loop). The Marathon doubles the Half Marathon route.Runners encounter diverse terrain—from beautiful single-track thr..

Mt. A Trail Challenge is an annual event held at Mount Agamenticus in York, Maine. Runners and walkers choose between a 5K or a 1-mile course.The race is timed in a traditional way by the York High School Cross Country Team, creating a friendly, community atmosphere. The 5K course climbs around the..

Kilkenny Ridge Race, part of Aravaipa’s White Mountain Endurance Cup, takes place in Stark and Jefferson, New Hampshire, on the Kilkenny Ridge Trail through the White Mountain National Forest. It offers 50-mile, 25-mile, and 25K races along a roughly 25-mile traverse with about 7,500 feet of climb p..

The Royal (multi) Mile Hill Run is a 5K trail race held in Lincoln, New Hampshire, as part of the 50th Annual NH Highland Games & Festival. The challenging course features 800 feet of elevation gain across dirt trails, service roads, and ski trails at Loon Mountain. Participants receive a race shirt..

The TAM Trek is a trail race and fun run held on September 21, 2025 in Middlebury, Vermont. It is the 22nd annual running of the event and raises funds for the Trail Around Middlebury (TAM). The TAM is a 19-mile footpath that encircles the village of Middlebury and links several hundred acres of to..

The Westmore Mountain Challenge is a one-day trail run in Vermont’s Northeast Kingdom, covering five mountains—Moose, Hor, Pisgah, Haystack and Bald—for a total distance of about 26 miles and roughly 6,100 feet of elevation gain. The course traverses public trails on steep terrain, with a shuttle-as..

Farm to Farm Ultra is a Maine ultramarathon held in Freeport and Brunswick. The 2025 event includes a 50-mile race, a 50K, a 50K four-person relay, plus 25K and a 25K two-person relay. The course starts at Wolfe’s Neck Farm in Freeport and finishes at Crystal Spring Farm in Brunswick, featuring roll..

The Pleasant Mountain Race, held in Bridgton, Maine, is a challenging 21k trail run featuring technical single-track paths and scenic views along Pleasant Mountain’s iconic ridge. The course includes significant elevation gains, with a steep 1700-foot climb over 2 miles up Bald Peak, followed by a 1..

The Vermont 50 Ultra Run is part of the Vermont 50 endurance weekend held at Ascutney Outdoors in West Windsor, Vermont. It includes a 50‑mile Ultra Run and a 50K Run, plus related relay options and other activities that showcase a challenging yet scenic Vermont landscape. Runners traverse the hills..

Moxie's Memorial 5k is a trail run/walk in Oxford, Maine, starting and finishing at Oxbow Beer Garden on Main Street. The 5K course starts at the brewery, runs along the blue ski trail (Anne's Moon Dance) to the Mission Working Dogs training center via a connector to Moxie's Place, then returns. The..

Bobcat Ridge 25k is a 25-kilometer trail race held at the Edwin L. Smith Preserve Trailhead, Guinea Road, Kennebunkport, Maine. Runners will test themselves on challenging, scenic forest trails along the preserve’s network.The event benefits the Kennebunkport Conservation Trust, with all proceeds su..

Bubba's Backyard Ultra, now in its seventh edition, takes place at 564 Stark Rd, Center Conway, New Hampshire, in the White Mountains. The event uses the Last Person Standing format, with participants running repeat 3.5-mile laps, mostly forest singletrack with sections of snowmobile trail, fields,..

The Little Duck 50k is a trail running event held in Windham, Maine, at the scenic East Windham Conservation Area. Scheduled for October 5, 2025, it offers two race distances: a challenging 50k ultra-marathon consisting of five 6.5-mile loops with nearly 1,000 feet of elevation gain per loop, and a..

Trust Trail Fest, hosted by the Kennebunkport Conservation Trust, takes place at the trust's headquarters in Kennebunkport, Maine (57 Gravelly Brook Road). Participants choose a 5k or 10k and run or walk along the organization’s forest trails. The course winds through the trail system, with rough te..

Groton Town Forest Trail Races, held at 163 West Main Street, Groton, MA, offer two trail distances: 9.5 miles and 3.4 miles. The courses are well-marked and feature a scenic loop through Groton Town Forest with no road crossings, combining narrow dirt roads and single-track trails over roots, rocks..

Keene Family YMCA Fall Foliage Trail Races in Keene, New Hampshire offer 5K and 10K trail runs starting and finishing at the Keene YMCA (200 Summit Road). The 5K provides a fast, beginner-friendly taste of trail running, while the 10K adds more challenging rolling singletrack and elevation. Runners..

Blackhawk Blaze is a trail running event held in Plainfield, New Hampshire (Meriden area), at 92 Bonner Road, near Plainfield School. This sixth annual Plainfield tradition offers two races: a 5K Trail Race on the famed French's Ledges trail and a 1 Mile Fun Run. The course showcases rugged terrain..