Trail Running calendar near Valley Cottage 2025-2026

Join A Run to Remember on May 2 in Red Hook and run or walk scenic farm trails through meadows, orchards, and woods at Greig Farm. Honor loved ones, celebrate community spirit, and vie for cash prizes in the 5K and 10K races.

Take on Breakneck Point on May 3, 2026 in Beacon, NY with a rugged half or full ultramarathon featuring huge elevation and technical single track. Expect steep exposed climbs, aid stations, and a finisher shirt and memento.

Run or walk the fifth annual Green Traill 5K in Easton on May 3, 2026 at Easton Cemetery, a volunteer run raising funds for Friends of Historic Easton Cemetery. Enjoy a timed 5K, a 2 mile walk, kids fun run and post race refreshments.

Blue 2 Blue Challenge is a rugged 50K through New Haven trails, with about 6350 ft of climbing and technical rocky terrain including a summit at Mt Sanford. Expect a cutoff driven, no frills race for seasoned trail runners.

Trails To the Sky at Voorhees State Park invites runners to tackle a scenic, hilly trail course with a UTMB index 50k and a shorter 10k option. Expect rugged singletrack, observatory views, friendly aid stations, and custom finisher medals.

Run a scenic 5 mile trail at Muscoot Farm with kids races for ages 2 to 12 and a family friendly vibe. Finish with Farm Bucks to spend at the Muscoot Farmers Market and optional shirts available by advance order.

C'mon Armageddon is a rugged trail race in Norvin Green State Park NJ offering 50K, 10M and 5M routes over boulder fields, river crossings and rocky peaks with skyline views. Big climbs and technical terrain make it a true test.

Run Like The Wind 5K in Ellenville offers a scenic course along the Shawangunk Mountains and the newly resurfaced Rail Trail. Finish at Aroma Thyme Bistro for garden drinks and food while supporting local food pantries and youth scholarship..

Recharge your trail legs with a small group spring camp in Oliverea, NY, in the Catskills. Tackle technical scrambles and big climbs while getting on trail coaching and mental performance work to sharpen your skills and confidence.

Run a scenic 5K through Blydenburgh County Park in Smithtown on May 23, 2026, with a free Kiddie Dash for kids. Join in person or virtually, enjoy trails and post race refreshments while supporting the Never Stop Running Foundation.

Run the Mine Hill half marathon on 24 May 2026 in Roxbury Connecticut, starting and finishing at Mine Hill Distillery. Enjoy rolling country roads with sweeping farm views, then celebrate at the distillery after party.

IronHike Series Spring 26 takes place June 4 to 7 at Mohawk Mountain, CT, with solo and team endurance options from 15 to 152 miles. This non competitive FlexRelay invites crews to self manage pacing, rest and night trekking.

The Norbrook Farm Brewery Trail Festival will take place in Colebrook on Saturday 13 June 2026. You can run between 5 and 4 hours.

Join XTERRA's Transcend Trail Run at Dickerson Mine Preserve for fast, flowy lakeside singletrack and accessible routes for all abilities. Finish at Black River Barn with outdoor dining and beer on tap and choose from 21K, 10K or 5K.

Run Pinky’s Rock n Rolla on July 11 in Richmond Hill NY: a rugged 4 mile trail through 100 year old pines and Queens longest oak forest. All finishers get medals, top three earn prizes, dogs welcome, and proceeds benefit Puppy Kitty NYCity.

Run the Ridge Reaper at Ward Pound Ridge Reservation with 25K, 50K, and 50M courses through technical singletrack and scenic carriage roads. Big climbs, ridge views, and a cupless format so carry your own hydration.

Interstate 17 is a challenging 17 mile trail run on August 8, 2026 in Closter NJ that traces Hudson River viewpoints. Expect rugged technical singletrack, steep climbs and boulder scrambles across four loops with fully stocked aid stations.

Thunder Chicken Squatch invites trail runners and hikers to tackle technical rock and root trails at Stokes State Forest in Branchville NJ on Sunday, August 9, 2026. Choose 5K, 10K with a ruck division, or a 17 mile loop with aid stations a..

Tackle scenic ski area trails at Belleayre Mountain in Climb It For Climate, a community trail race offering challenging 25K and shorter 8K options. Proceeds support The Catskill Center and registration includes a zero carbon travel offset.

Tackle the Shawangunk Ridge Trail near Rosendale NY for sweeping Hudson Valley views across cliffs, sky lakes and rocky ridgelines. Choose 70 Miler, 30 Miler or half marathon for a rugged, self supported navigation challenge.