Trail Running calendar near Bolton Landing 2025-2026

Celebrate Thanksgiving in Springfield VT at Toonerville Trail Turkey Trot, a flat, scenic 5K along the Black River with a virtual option to support local food banks and school teams. Finishers get socks and cider donuts.

Join Krampuslauf in Lyme NH for a festive mountain trail run from the Dartmouth Ski Way lodge, offering 5K, 10K and a 9 hour multi lap challenge. Finish loops to earn a 10K medal with pins and upgrades to a 50K medal.

Get festive at the Ugly Sweater 5K in Canajoharie on December 6, 2025, where runners and walkers hit the scenic Erie Canal trail in holiday style. All proceeds support the Community Youth Center and age group prizes add extra fun for racers..

Runamuck 50K is a rugged trail ultramarathon around South Pomfret, Vermont, weaving hilly dirt roads and scenic backcountry. Expect changeable weather and a true test of endurance on this challenging 50K course.

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

Infinitus is a multi day endurance festival May 21 to 30 in Ripton, Vermont, offering distances from 9 miles to the epic 888K 551 mile challenge. Set at Silver Towers near Green Mountain National Forest, it features dorm lodging, camping an..

Take on scenic trails around Trapp Family Lodge in Stowe, Vermont on June 20, 2026 with 25K or 50K options. Enjoy rolling climbs through pastures and hardwood forest, stocked aid stations, and a festive finish at the Von Trapp estate.

Take on a rugged 8.2 mile trail in Killington Vermont with 3,010 ft of climbing. Summit Killington Peak and two others, tackle technical terrain, and vie for cash and gear in a field capped at 700 runners.

Run to the summit on July 4 at the Whiteface Mountain Races in Wilmington NY, with steep, technical mountain courses and a scenic summit finish. Options include 10k, 21k, the uphill Ascent and a kids Klymber.

Scenic 5K and 10K trail races through the Green Mountain National Forest at Blueberry Hill Outdoor Center in Goshen. Proceeds support the center and registration opens Nov 1, 2025.

Run the Triple Dam 10K in Perkinsville VT on August 23, 2026 for a scenic road and trail loop with a fun calf deep river crossing. Open to runners and walkers, proceeds support Springfield High School cross country.

Challenge yourself at the Vermont 50, a legendary mountain bike and ultra run at Ascutney Outdoors. Join racers, relays, vendors and kids fun races while supporting Vermont Adaptive on Sept 27, 2026.

Amy's Adventure Race for the Lake features scenic 4.5 mile and 10 mile trail courses through Amy's Park with ponds, marshes and about 700 feet of climbing. Proceeds benefit Lake George Land Conservancy and virtual entries are welcome.

Take on the Trapp Lodge Mountain Marathon in Stowe Vermont with half and full options on a rugged 13.1 mile loop that climbs Round Top. Expect sweeping mountain views, big elevation gain, and post race food and a shirt.