Trail Running calendar near Milton 2025-2026

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..

ELEVATE, MONTREAL - Défi Du Sentier D'élévation, by City Shred, takes place at Ski Saint-Bruno in Saint-Bruno-de-Montarville, QC, just outside Montreal. The event offers adult distances of 5K, 10K and MAX Elevation, plus a 20K Relay (team of four), along with kids’ routes of 1K, 2K and MAX Elevation..

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..

Défi Everest Orford is a charity sporting event presented by Défi Sportif AlterGo at Mont Orford in Orford, Quebec, Canada. The 6th edition runs September 18–21, 2025, offering an inclusive mountain ascent across all weather, with volunteer randonneurs helping participants with functional limitation..

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..

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..

Tam Trek is a trail race in Middlebury, Vermont, organized by the Middlebury Area Land Trust to raise funds for the Trail Around Middlebury (TAM). Races start and finish at Wright Park and include a 19-mile TAM loop through Middlebury, Cornwall, New Haven and Weybridge; a 10K; a 5K; and a 2-mile fam..

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..

Amy’s Adventure Race for the Lake, now in its 9th year, takes place at Amy’s Park in Bolton Landing, NY. The event offers a 4.5-mile trail race and a 10-mile loop through forests, ponds, and marshes, featuring rugged Adirondack terrain with about 700 feet of elevation gain. Proceeds support the Lake..

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..

The Bromont Ultra is a renowned ultramarathon and mountain biking event held in Bromont, Quebec, Canada, set amidst the scenic Eastern Townships. Since 2014, it has combined physical endurance challenges with philanthropy, raising over $4 million for various causes. The event features diverse trail..

Trapp Lodge Mountain Marathon is a challenging trail running event held at Trapp Family Lodge in Stowe, Vermont, offering half and full marathon distances. The course blends runnable double-track with rugged single-track, including a scrambling climb to Round Top Mountain for sweeping views of Mount..

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..

RutFest (Richmond Ultra Trail Festival) is the Richmond Trail Running Club’s fifth annual weekend trail festival in Williston, Vermont. The 36-hour event at Catamount Outdoor Family Center features two repeatable trail loops of about 3 and 4 miles on the north and south sides of Catamount, offering..

The CircumVictory Trail Run will take place in Victory on Saturday 1 November 2025. You can run between 17 and 17 miles.

Krampuslauf in Lyme, New Hampshire, at the Dartmouth Ski Way, offers 5K, 10K, and a 9‑hour endurance option. Runners begin at the base lodge and tackle Holt’s side for a steep 5K ascent; 10K participants complete Holt’s and then Winslow side before finishing by the lodge. The 9‑hour loop repeats the..

Infinitus 2026 in Ripton, Vermont, organized by The Endurance Society, is a multi-distance endurance festival with races from 9 miles to 551 miles (the 888K). Distances include the 9 Miler, Marathon, 88K, 100 Miler, Deca-Marathon, 250 Mile, Penta-Marathon, and the 888K. The course is documented on A..

The Whiteface Mountain Races, held in Wilmington, NY, offer a challenging mountain running experience with some of the greatest vertical gain and loss per mile in the U.S. The event features multiple race options including a 21K (two loops), 10K (one loop), Vert Junky combo, 4K Ascent, and a 1-mile..

The Goshen Gallop is an annual trail running event held at the Blueberry Hill Outdoor Center in Goshen, Vermont. Celebrating its 48th year in 2026, the race offers 5K and 10K distances over well-marked courses featuring rugged gravel roads and cross-country ski trails within the Moosalamoo National..