Trail Running calendar near Chelsea 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 Champlain Bridge 5K and 2 Mile Fun Run/Walk is a family-friendly event held at Crown Point State Historic Site and DEC Campsite in Crown Point, New York. The scenic 5K cross-country course winds through trails, roads, and fields, symbolizing hope and connection through the lighthouse and bridge..

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..

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..

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..

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..

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,..

Amy’s Adventure Race for the Lake, hosted by the Lake George Land Conservancy, takes place at Amy’s Park in Bolton Landing, NY. The event offers two trail options: a 4.5-mile race and a 10-mile loop, featuring rugged single-track through forests, ponds and marshes with about 700 feet of elevation ga..

The Buck 50 is a challenging 50-kilometer ultramarathon held in Kattskill Bay, New York, along the scenic southern Adirondacks near Lake George. The course features rugged, remote trails that traverse four of Lake George's tallest peaks, including Buck Mountain, Sleeping Beauty, Black Mountain, and..

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..

Devil's Den Ultra is a challenging trail running event held in Bradford, Vermont, featuring a rugged 10K loop on Wright's Mountain. The course offers a mix of terrain, including steep climbs, rocky and rooty sections, and a scenic downhill through the woods. Runners can choose from three race option..

Fall Foliage Foot Races at Waterville Valley, NH, 2025 offers three events: a 5K Road Race, a 10 Mile Trail Race, and a Kid's Fun Run. The action centers in Town Square, with a mostly flat 5K out-and-back through the heart of Waterville Valley. The 10 Mile Trail Race is described as a scenic and cha..

The North Face Race to the Summit is a mountain-top running event held at Stratton Mountain in Stratton, Vermont. The course covers about 2.18 miles with a 2,003-foot vertical climb, delivering a steep uphill challenge amid alpine terrain. The race is timed with live results and leaderboards, with o..

The Trapp Lodge Mountain Marathon takes place at Trapp Family Lodge in Stowe, Vermont on October 18, 2025. The event offers two distances: Full Marathon - 26.2 miles (two 13.1-mile laps) Half Marathon - 13.1-mile loop Entry fees vary by date, with early, regular, and day-of pricing for both dista..

Randolph Ramble is a 5.7-mile trail race on Randolph Mountain Club lands in New Hampshire’s Northern Presidentials. The course climbs about 1,100 feet and is steep, rocky, and slippery, with occasional snow; most runners walk or power-hike the technical sections. Expect leafy downhills to be treache..

The Hills Are Alive Cross Country Race, now themed as the Ghostly Gallop Trail 5K, is held at Arrowhead Golf Course in Milton, Vermont. The 5K course runs along the scenic Laura’s Tears trail, offering a trail running experience with a festive Halloween atmosphere encouraging participants to wear co..