Trail Running calendar near Windham 2026-2027

A loop trail run at Lawson Lake Park on June 20, 2026, featuring a 1.25 mile course with lake and creek views. Options include 2.5M, 5M, a one-hour format, and team entries; awards and a meal ticket are included.

An 8.6 mile trail run at Minnewaska State Park Preserve on June 24 with chip timing and commemorative towels for finishers. Entry is limited to 250 runners and parking carries a 10 USD per car fee.

A night 5K at Lakeside Park with mixed trail terrain, reflective markers, and required personal lighting; finishes receive handmade medals and proceeds benefit the Pawling Recreation Department.

A trail event at Red Wing Recreation Area on July 5, 2026 offering 60K, 30K and 15K on a 15k loop with mixed surfaces, aid stations, lap-support for 60K runners, and awards for top finishers.

Notchview Ultra runs July 10-13, 2026 at Notchview in Windsor, MA using a 1.9 mile loop with an aid station and bathrooms. Multiple timed and distance formats are offered, with campsite options and beneficiaries including local conservation..

Muddy Princess Albany is a 5 km obstacle mud run for women held at Harley Rendezvous Classic Inc. Join this non competitive event focused on unity and empowerment while supporting the fight against breast cancer.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

A remote *55K* ultramarathon on the Northville Placid Trail in Adirondack Park, featuring technical terrain, about 3300 feet of gain, self-supported running, a required validation race, and registration that includes a shirt and two meals.

Trail and dirt road races at Beartown State Forest on July 19, 2026. A 5 mile trail with steep sections and a 13.1 mile course with about 1,600 feet of climb, set cutoffs and limited amenities.

A third annual cross country event in Warwick, NY on July 25, 2026 featuring a 5k mass start race and a free 400 m kids dash where all youth finishers receive a ribbon.

A rugged 30K trail run in Windham, NY with an in-person race in late July and a virtual option through August. Entry is by approval with strict qualifying standards and the field is limited to 275 runners.

Experience the wooded trails of the historic Ward Pound Ridge Reservation in New York. This event offers 25K, 50K, and 50 mile distances featuring a mix of technical singletrack and runnable carriage roads.

An eight hour track ultramarathon at Clapp Park in Pittsfield, MA, run on a certified 0.355 mile dirt and cinder loop with lap counting, midrace direction change, bottle drop aid station, awards, and proceeds benefiting the AYJ Fund.

The third annual Tappen Brook 5K in Bridgewater, CT, uses newly opened trails through Bridgewater Town Park with packed dirt and natural paths and views of Lake Lillinonah. Participants receive a race-day gift and top finishers earn prizes.

Trail races at Fahnestock State Park near Cold Spring NY offer three distances on mixed runnable dirt roads and technical single track. Multiple aid stations and a post race meal are provided and proceeds support park conservation.

Experience a rolling cross country run through the forests and meadows of the Landis Arboretum. This sanctioned 5K race offers views of the Schoharie Valley and access to scenic trails and gardens.

Climb It For Climate at Belleayre Resort on August 16, 2026 offers 25K and 8K mountain courses open to runners and hikers, offsets its carbon footprint, and raises funds for The Catskill Center.

A 6 hour loop ultra and a 4.2 mile memorial run at Jug End State Reservation in Egremont, MA on August 22, 2026. The 4.2 mile trail runs through woods, fields and an apple orchard with about 830 feet elevation per lap.

This 4-mile trail run in Schenectady Central Park uses a flexible time trial format. All proceeds support addiction recovery services, honoring a personal legacy. A pre race stretching session is included.

A five kilometer trail run through the hills of Butternut Valley in Garrattsville, NY on August 22, 2026. Staged at Butternuts Beer and Ale as part of Butternut Valley Days, with a registration fee of $35.