Trail Running calendar near Rensselaerville 2026-2027

A muddy obstacle-course festival in Deansboro, New York offering 5 mile, 5K and kids runs plus live music and local brews. Proceeds support the Barden Adventure Scholarship and other charitable efforts.

The A Run to Remember will take place in Red Hook on Saturday 2 May 2026. You can run between 5 and 10 kilometers.

Rock The Ridge is a fundraising trail event at Mohonk Preserve on May 2, 2026. Options include a 50 mile ultra, a 26.2 mile trail marathon and relay teams, with proceeds supporting conservation and education.

A technical trail half and full marathon at University Settlement Camp in Beacon, NY on May 3, 2026, featuring steep, exposed climbs and substantial elevation gain with official aid stations and strict cut-off times.

A four race 5 km trail series at Cole's Woods in Glens Falls across Tuesdays in May, with a 20 km challenge for those who complete all four events. Entry fees, T shirt allocation, awards and proceeds benefiting the Glens Falls Youth Center..

The Towpath Trail Run in Saint Johnsville offers a flat, paved course for a 10K and a 5K run/walk. Professional timing ensures accurate results. The event is scheduled for May 9, 2026.

Run for a cause at the Bruynswick Winery Run, a 6k cross-country race benefiting the Ulster County SPCA. Enjoy a scenic course at the foot of the Shawangunk Ridge, with music, drinks, and a chance to meet shelter animals. Free children's da..

A 5K trail run through the orchard at Indian Ladder Farms on May 10, 2026, with a hard cider mimosa provided after the finish and non alcoholic options; top 1st to 3rd place finishers aged 21 and over receive craft cider bottles.

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

Annual May races on the Ashuwillticook Rail Trail offering marathon, half and 8K distances starting and finishing at the Adams Visitors Center. Proceeds support the rail trail and a municipal fund for the City of Pittsfield.

Tails & Trails State Forest Run in Pittsfield State Park on May 16, 2026 features 50K, 25K and a 5 mile loop of single track, pine forests and mountain bike style trails while supporting local animal rescues.

Event Overview The Ledge Rock Hill Wine Run 5K takes place at the Ledge Rock Hill Winery in Lake George, New York. The event features a 5K distance, which is open to participants aged 1 to 99. It is a timed race, with professional timing an..

Celebrate a Hudson Valley tradition dating back to 1983 with the Run Like The Wind 5K in Ellenville. This scenic course runs along the Shawangunk Mountains and features a section on the newly resurfaced Rail Trail. All event proceeds suppor..

Mine Hill Half Marathon is a 13.1 mile road race in Roxbury, Connecticut, with start and finish at Mine Hill Distillery. The course passes farms, fields and scenic vistas and includes a post-race gathering at the distillery.

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

Rise of the Obstacles in Wallkill NY on May 30-31 features adult and kids obstacle races including a 100 m sprint, a two-lap endurance course, and kids 50 m and 1 km heats. Events include finisher medals, age-group awards, a Teddy Bear Craw..

Coz's Backyard Ultra on May 30, 2026 in Holland Patent, NY uses the Backyard Ultra format. Runners complete a 3 1/3 mile loop each hour until one runner remains or the 30 hour limit is reached.

A running event in Granville on May 30, 2026: a relatively flat 5k along the rail trail finishing on the footbridge over the Mettowee, plus a kids 1k. Registration opens March 26; 5k fee $25, kids run free.

A choose your own adventure ultra and trail event at Chesterfield Gorge with multiple distances, lap based 50k to 100mi options, a 30 hour window for ultras, and timed 33k and 11k races the following day.

Multi-day elevation based endurance events at Mohawk Mountain in Connecticut, June 4 to 7, 2026. Solo, Trail Buddy and Trail Family formats cover timed events from a 12-hour 15-mile option up to 84-hour 152+ miles with large elevation gain.