Trail Running calendar near Randolph 2025-2026

The Last Man Standing Ultramarathon is a backyard ultra event held at Pineland Farms in New Gloucester, Maine. The race features a challenging 4.2-mile loop on wooded trails with moderate elevation gain. Participants must complete each loop within one hour to continue, with laps starting hourly unti..

Black Bear Trail Races, hosted by White Mountain Endurance in Waterville Valley, New Hampshire, offers four distances: a 50K ultramarathon, a 23K, a 4-mile forest trail run, and a 1-mile Bear Cub Fun Run for families. All courses start and finish at Waterville Valley Town Square. The 50K loops aroun..

Jay Peak Trail Running Festival takes place at Jay Peak's Stateside base in Jay, Vermont, over Labor Day weekend (Aug 30–31) and offers two days of trail races for all ages and abilities. The festival provides a spectrum of trail distances, from accessible 5Ks to more demanding routes, including an..

The Five Fields Farm Races, held in Bridgton, Maine, feature two challenging trail events: a 50K ultra and a 10K race. The 50K is a three-lap figure-8 course through the Bald Pate and Holt Pond Preserves, including steep climbs, technical singletrack, and a finish through an apple orchard. Each lap..

The Big Day Brewing Fall Trail Running/Walking Series takes place at Great Glen Trails, with base-lodge facilities and courtyard check-in. Participants may choose from three courses—long 5 km, short 3 km, or mini 1.5 km—with the course varying each fall. Registration is online (free) or in person at..

Groton Forest Trail Run takes place at Boulder Beach State Park in Groton, Vermont, on Saturday, September 6, 2025. Onion River Outdoors is the new race organizer, continuing the event’s tradition of scenic, challenging trail running and strong community support. For 2025 the organizers plan a 25k a..

Cherry Hill Farm Ultra in Gorham, Maine offers two trail options: a 50K and a 25K, run on a flat, fast, non-technical loop around Cherry Hill Farm. The 50K comprises 12 laps of 2.6 miles (31.2 total), while the 25K is six laps. The course threads along the Ecomaine Trail, Burleigh Lovett Trail, Cana..

Down for Trail Running is a trail-running weekend in western Maine, held at Mirror Lake in West Newfield. Runners navigate a looping course of forest roads, single-track, rugged sections, and climbs, with each lap roughly 3.6 miles—participants choose how many laps to complete. The course provides a..

The Happy Moose Half Marathon is a 13.1-mile trail race held in Oxford, Maine, featuring a scenic course through the fields and forests of western Maine. The race consists of three loops of the 4.1-mile Four in the Forest course, plus a separate 0.8-mile loop at the start. This event offers runners..

NCVRC Run for Hope takes place at Oxbow Riverfront Park in Morrisville, Vermont. The course is an out-and-back along the Lamoille Valley Rail Trail, with a turnaround at 1.5 miles and a single aid station before finishing back at Oxbow Park, for a total distance of about 3 miles. Race bib pickup run..

Four in the Forest is a four-mile trail race held in Oxford, Maine (04270). The course traverses forested areas and open fields in western Maine, offering a scenic, nature-forward experience for trail runners. Runners tackle a predominantly off-road route along Bennett Lane, with a setting that emph..

The Kismet Cliff Run, held annually in September in North Conway, New Hampshire, offers two challenging trail races set in the scenic White Mountains. Participants can choose the Little Beast 5 Miler, featuring technical single-track trails with steep ascents and descents around Echo Lake State Park..

The Gunstock 5K and Canicross 5K take place at Gunstock Mountain Resort in Gilford, NH, as part of the annual Food Truck Festival. The event features a 5K trail run and a Canicross 5K where participants run with their dogs, followed by a 100m fun run for children under five. The course is a loop aro..

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 ACT Trail Fest, held in Arundel, Maine, is an annual trail running event featuring 5k, 10k, and half marathon distances. Participants run or walk through the scenic Arundel Community Trails and Eastern Trail, enjoying woodland and stream views. The race starts and finishes at the Arundel Municip..

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 Westmore Mountain Challenge is a one-day, 26-mile trail running and hiking event in Vermont's Northeast Kingdom, featuring five mountains: Moose, Hor, Pisgah, Haystack, and Bald. Participants traverse rugged public trails with a cumulative elevation gain of about 6,142 feet, enjoying spectacular..

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..