Trail Running calendar near Jackson 2025-2026

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..

Moxie's Memorial 5k takes place on September 28, 2025 in Oxford, Maine. The event starts and ends at Oxbow Beer Garden and benefits the nonprofit Mission Working Dogs. The fundraiser had raised $4,122.42 toward a $10,000 goal (41% of the goal) and showed 103 participants listed at the time of the p..

The Bobcat Ridge 25k is a 25k trail race held on the trails of the Edwin L. Smith Preserve in Kennebunkport, Maine. The event takes place on Saturday, October 4, 2025, at the Edwin L. Smith Preserve Trailhead on Guinea Road. All proceeds from the race go directly to the Kennebunkport Conservation T..

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 takes place on October 5, 2025 at the Kennebunkport Conservation Trust headquarters, 57 Gravelly Brook Road, Kennebunkport, ME. Participants can choose a trail 5k or 10k course that winds through the KCT trail system and finishes at the headquarters. The courses are on forest trail..

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 Land of Light 100k is a unique human-powered race held in Norway, Maine, featuring a combination of running and cycling across six distinct trail systems. The event covers a total of 100 kilometers, with 25k of running and 75k of cycling, starting at Virgil Parris Preserve. Participants navigate..

Vulcan's Fury Trail Race in Nottingham, New Hampshire offers two rugged courses—the Half Marathon and the 5 Miler—set on hiking trails through a once volcanic landscape at Pawtuck. The course is described as technical and scenic, featuring a massive boulder field, dense forest, single-track switchba..

Sugarloaf Uphill Climb is Maine’s toughest mountain run in Carrabassett Valley. The three-mile course climbs nearly 2,500 feet from the bottom of the SuperQuad to the resort’s 4,237-foot summit—the top of Maine’s second-highest peak—along the Binder Trail and work road. The race uses a mass start an..

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..

The Mansfield Uphill run is hosted by the Mansfield Nordic Pro Team at Stowe Mountain Resort on October 19, 2025. Proceeds will go directly to supporting the Pro Team athletes and program. The team is fundraising to help offset costs for Supertour and World Cup race trips, ski wax, test skis, warm-..

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 Thorne Head Trail Run is a community-focused 4k trail race held at Thorne Head Preserve in Bath, Maine. Hosted by the Kennebec Estuary Land Trust, this event features a mix of fun single-track and wider trails with scenic water views. Designed to be inclusive for both first-time trail runners an..

Located at Lost Valley in Auburn, Maine, the Maine Summit Trek for Tree is a community fundraising event hosted by Lost Valley to benefit Tree Street Youth. The centerpiece is the Endurance Hiking Challenge: participants run, hike, or walk the Access Road to the summit, then descend by chair lift or..

Big Brad Ultras is an ultramarathon event in Pownal, Maine, weaving through Bradbury Mountain State Park and surrounding trails. Distances include 50 Miler, 50K, and 25K, all run on a 16.5-mile loop of Maine singletrack with climbs over Tryon Mountain, Snowman’s loop, and back into the state park. T..