Trail Running calendar near Cheshire 2026-2027

Tackle a scenic 5K or 8K through Pindar Vineyards on flat packed trails while supporting the NY Cancer Foundation. Finish with live music, food trucks and a complimentary glass of Pindar wine for a festive fall celebration.

Take on the NipMuck Trail Marathon in Ashford CT on October 4, 2026, a rugged 26.4 miles out and back across rocks, roots, mud and scenic wood bridges. Organized by the Shenipsit Striders, the race supports Connecticut trail stewardship.

Paine to Pain Trail Half Marathon offers a scenic single loop through five Westchester parks, with 90 percent on dirt trails, roots and rocks under tree cover. Expect abundant wildlife, quiet forest passages and a true trail running challen..

Join the Suffolk County Marathon weekend in Bay Shore, NY on October 17 and 18, 2026, with races from a 1K kids run to the full marathon. Enjoy combined weekend challenges, youth events, and a virtual option to race your way.

Join a scenic trail run through NE Connecticut along the Air Line State Park Trail with marathon, half, 10K, relay and junior distances. Tackle the Trail supports local students pursuing higher education.

Big Bear SquaTCh South is a technical single loop trail race in Harriman State Park on October 18, 2026, with steep climbs, rocky descents and a short scramble. Pick the half marathon or the 10K; spots are capped at 175 and fill fast.

Discover scenic single track trails at Grills Preserve in Westerly on October 24, 2026 with 10 mile and 10K options. Choose a distance and enjoy riverfront views and bridges as race two of the WTAC Fall Trail Race Series.

Take on a scenic 5 mile trail run through Muscoot Farm in Katonah on Oct 25 with kids races for young runners. Cross the finish to collect Farm Bucks to spend at the Muscoot Farmer's Market and enjoy a festive community atmosphere.

Late autumn weekend at Red Wing Recreation Area with looped 100k, 50k and 10k races over rugged, hilly trails. Expect big elevation, full aid, camping for 50k runners and finisher awards, with UTMB Index status for longer distances.

Join 8 Hours at the Farm at Gurski Farm in Brookfield CT. Run repeated 4 mile loops on rolling single track and farm trails in a community driven, spectator friendly trail running experience.

Pocantico Hills Races at Rockwood Hall in Tarrytown on November 7, 2026 feature marathon and half marathon loop courses on wide carriage roads. Expect rolling climbs, Hudson River and Palisades views, fields, forests and car free trails.

Take on the Raven Rocks Run 10k through rocky climbs, ridgelines, ravines and hilly meadows at Ward Pound Ridge Reservation. This scenic but challenging trail route finishes by the old fire tower and closes out the Trail Mix series.

Tarrywile Half Marathon on November 16 2025 challenges runners with technical single track, about 3,000 feet of climbing, and sweeping park views. Choose 10K, half or full marathon in scenic Tarrywile Park.

Enjoy scenic trails around Watchaug Pond at the Li'l Rhody Runaround on November 15, 2026, with 8 mile and 4 mile course options. Part of the WTAC Fall Trail Race Series, it welcomes runners of all levels.

Run the Storybook Half at Roosevelt Forest: a 13.1 mile trail of eight scenic loops on singletrack and doubletrack with roots, rocks, and rolling hills. Bring kids books to donate and earn a medallion and costume prizes.

Join the Soul n Body Thanksgiving Trail Run in Wolcott CT for a spirited 3.5 mile loop around Mill Pond Way, complete with finisher medals, swag and post race yoga. Proceeds benefit endometriosis research and furry friends are welcome.

Hit the trails at Rob's Trail Run Edition in Woodbury on Sunday, November 29, 2026. Choose a 5K for adults or youth and enjoy scenic singletrack through Stillwell Woods Preserve.

The Frosty Forest 5K will take place in Stratford on Saturday 19 December 2026. You can run 5 kilometers.