Trail Running calendar near Wilmington 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 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..

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..

The Frightening Fall Trail Race, organized by Cornwall Multisport Club, is held at Guindon Park East, on Vincent Massey Drive in Cornwall, Ontario. Distances offered are 6 km (a prediction-style race; free for CMC members, $20 for non-members), 12 km ($30), and 18 km ($40). The event channels a Hall..

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-..

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 Jeff RUN sonville Turkey Trot is scheduled for Thursday, November 27, 2025, in Jeffersonville, VT 05464. The event is organized by the Jeff RUN sonville Run Club and is described as the inaugural running of this town turkey trot. The race site is listed at 201-37 Cambridge Junction Rd. Distance..

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..