Trail Running calendar near Randolph 2026-2027

Run the Vineyards in Unionville invites runners and walkers to scenic 5K and 8K trail courses through vineyard rows with live results and lively post race music. Every finisher receives a stemless wine glass and a post race pour, plus a tec..

Forbidden Run Fest takes runners through scenic Wissahickon Valley Park with 10K, 10 mile and half marathon options on gravel, dirt and single track trails. Limited to 750 entries, all finishers get a medal and sweatshirt and enjoy post rac..

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.

Trail races at Tarrywile Park near Danbury offering 10K, half marathon and marathon distances with technical single track, substantial elevation and lake views.

A trail half marathon in Roosevelt Forest, Stratford, run as eight laps of a 1.64 mile wooded loop with roots, rocks and rolling hills. The event features a children’s book drive, costume prizes, a finisher medallion and on-course aid.

Take on a rugged 5 mile lollipop loop in Lewis Morris Park with rocks, roots and about 600 feet of climb for a true trail challenge. Limited to 120 runners, the cupless, eco friendly event features reusable cups and hemp race bibs.

Squatchy Leftovers on Nov 28, 2026 at South Mountain Reservation in West Orange NJ offers 50K, 25K, 10K, 5K and a kids mile on a scenic 5K loop of mixed singletrack and carriage roads. Race supports Bigger Than The Trail.

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.

Take on The Naked Nick at Blue Marsh Lake in Leesport, PA on Dec 13, 2026 with 25K and 50K options over scenic singletrack and gravel trails. Expect rugged winter conditions, mid race aid and hearty post race food and awards.

Frosty Looper is on December 13, 2026 at Cooper River Park in Pennsauken, NJ, on a fast flat 3.75 mile loop with Philly skyline and lake views. Presented by HOKA, expect race swag, a stocked aid station and an 8 Hour challenge.

A 5K trail run through Roosevelt Forest in Stratford, CT on December 19, 2026, with awards for the top three men and women and a custom finisher medallion. A portion of proceeds supports local charities.