Trail Running calendar near East Hampton 2025-2026

Tackle the scenic Seven Sisters Trail Race in Amherst, MA on May 2, 2026, an out and back along the Holyoke Range ridgecrest. This rugged 12 mile course delivers steep climbs, rocky singletrack and over 3,500 ft of elevation for a thrilling..

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.

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.

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.

Run the Mount Archer Trail Race Sunday May 3 2026 in Lyme CT with a scenic 9.2 mile loop or a 3 mile option for runners and walkers. Chip timing, aid stations, and proceeds support Lyme emergency services.

TARC Wapack and Back is a rugged trail race along the Wapack Trail in Ashburnham offering 21.5, 43 and 50 mile options. Expect technical rocky singletrack, big climbs and limited entries so register early for a backcountry challenge.

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.

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.

Explore trails around Soapstone Mountain and Shenipsit Forest at the Soapstone Mountain Trail Races in Stafford Springs, CT on May 17, 2026. Pick a half marathon or 6K, support local trail stewardship, and register January 1, 2026.

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.

Run a scenic 3 mile trail through farm fields and finish among the vineyard rows at Westport Rivers Vineyard and Winery. Celebrate after with wine, music, BBQ and a souvenir glass for a festive postrun party.

Run the scenic 15.7 mile Nipmuck South Trail at Mansfield Hollow State Park, following the Nipmuck Trail along the Fenton River through woods, fields and a climb to a cliff. Proceeds benefit Connecticut trail stewardship groups and the Blue..

Notchview Ultra invites runners July 10 to 13, 2026 in Windsor, MA, offering formats from 100.7 miles down to 6 hour on a scenic 1.9 mile loop. Enjoy frequent aid, camping, swag, and proceeds supporting local conservation.

The Soapstone Assault is a rugged 5.5 mile trail race in Somers, CT with six climbs and about 1,500 feet of ascent. Limited to 50 runners, it is a tough course for experienced runners and includes a pre race safety briefing and breakfast.

Ridge Reaper Trail Runs on Aug 1, 2026 at Ward Pound Ridge, a scenic preserve 50 miles north of NYC. Choose 25K, 50K or 50 mile timed courses on technical singletrack and wide carriage roads with ridge views.

Join the Sweltering Summer Ultra, an 8 hour track challenge at Clapp Park in Pittsfield where runners and walkers lap a cinder loop and hit a marathon split. Chip timing, live leaderboard, refreshments and awards support the AYJ Fund.

Experience the Stonington Cross Country 5K at Stonington High School, a scenic route from the track through campus streets and wooded trails to a field finish. Family friendly with a kids half mile for ages 10 and under.