Trail Running calendar near West Windsor 2026-2027

Join the Millstone Madness Snowshoe Race on Feb 7 in Websterville VT for a scenic 3 mile loop around old granite quarries on single and double track trails. Snowshoes are required; enjoy friendly competition, prizes, warming fire and raffle..

An 8K snowshoe race at Camp Saratoga in Gansevoort, NY, with a 120 sq. in. snowshoe size requirement. Limited loaner snowshoes are available for a fee and the event benefits Wilton Wildlife Preserve & Park.

Snowshoe races at Moreau Lake State Park on February 28, 2026, with 15K and 4.7 mile single loops plus a kids 1 mile out and back. Snowshoes are mandatory and limited rentals are available on a first come first serve basis.

A **6K** snowshoe race at Gunstock Nordic Center with groomed trails, wooded single track, steep climbs, and marked course. Prizes include Dion snowshoes and age group gift cards, and limited rental snowshoes are available on race day.

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.

A 15K trail race at Grafton Lakes State Park covering about 9.3 miles with 900 ft of elevation gain. The technical yet runnable spring course can be muddy and is described as accessible for new trail runners.

A community race day in Elizabethtown, NY featuring a 13.1 mile half marathon, a new 5K trail race, and a kids 5K for ages 10 and under. Proceeds benefit Elizabethtown Community Hospital and local health programs.

A 12 mile out and back trail race on the Holyoke Ridge near Amherst MA featuring technical singletrack, over 3,500 feet of ascent, a 500 runner cap and a waitlist when full.

Take on the Dandelion Dash 5K or the Mushroom Mile on The Hartsbrook School trails, with a virtual option available. Muddy, scenic terrain and proceeds support the school's Land Stewardship program.

A spring trail race at Cochran's Ski Area in Richmond, VT on May 3, 2026, featuring a *7mi* steep course, timing, pancakes with Running Saps maple syrup, awards and raffle, with proceeds benefiting youth and a local nonprofit.

A technical trail race on the Wapack Trail in Ashburnham, MA on May 9, 2026, offering 21.5, 43 and 50 mile options over rocky single track and significant elevation. Registration is limited, manually timed, and nonrefundable.

A trail race on Winant Park Trails near downtown Concord with windy singletrack, switchbacks, and nordic type paths. Two distances are offered and proceeds benefit the Ralph Waldo Emerson School for Preschoolers; day of event entry is avail..

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.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

Run or walk the Ledge Rock Hill Wine Run 5k at Ledge Rock Hill Winery in Lake George on Sunday May 17 2026, a scenic vineyard course welcoming all paces. Enjoy a T shirt, collapsible wine glass and finisher medal while supporting Nik's Wish..

Annual May trail races on the Ashuwillticook Rail Trail including a marathon, half marathon, 8K and a free kids Mo Mile, with proceeds supporting trail maintenance in Pittsfield and event perks for participants.

A series of rugged trail races in Ripton, Vermont from May 21 to 31, 2026 offering distances from 9 miles to 250 miles plus multi‑marathon and ultra challenges. Camping is available for a one time fee; the event is cup free and no refunds.

A lap-based trail race in Keene NH using a 12.5 km loop with options up to 50 km, technical wooded terrain, aid stations, and a cupless policy requiring personal hydration gear.

The Chocorua Mountain Race will take place in Tamworth on Saturday 6 June 2026. You can run 23 kilometers.

Run a scenic 5 mile Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on Saturday, June 6, 2026. Enjoy family fun, food, and festivities while supporting the Fitzwilliam and Troy historical societies.