West Rock
Trail Running Calendar near West Rock 2026-2027
Explore the top trail runs near West Rock for 2026-2027! We've gathered 32 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
An obstacle-based 5K at Short Beach in Stratford that raises funds for the Sterling Community Center and includes 18 plus obstacles, shirts, medals and family participation rules.
A community trail event at Ives Farm featuring a 5K, an elementary school relay, a free Pumpkin Dash for young children, family activities, and free training sessions.
Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.
A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.
Trail races in Burlington CT on September 26, 2026 offering 8K and 5K routes on varied single and double track through Tunxis Trail landmarks.
October 2026
A 30 hour loop ultrarun in Roosevelt Forest CT on 2.5 mile laps offering distances to 100 miles with a finisher buckle and a single pavilion aid station.
Multi-day trail event in Rocky Point, NY on a 10.48 mile loop with distances from 10 to 150 miles, two stocked aid stations, and a strict no drop rule.
A 5K trail run and an accessible short run/walk on private Gemstone Farm in Wilton, CT on 10/10/2026, with farm access, post-event food and entertainment, supporting The Prospector.
A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.
Trail 5K and a kids one mile fun race on a 33 acre campus in Middlefield CT with breakfast treats and finisher medals.
An off road 50k through interconnected woodland preserves in southern Connecticut with rocky forest roads and single track, run as a non profit with awards and volunteer options.
November 2026
Timed trail running on a 4 mile loop at Gurski Farm in Brookfield CT with 8 hour and 4 hour options plus a new 5K Canicross for 2026.
An inaugural backyard ultra at Cranbury Park where runners repeat a 4.167 mile loop each hour until one runner remains, with crew access and central aid near the corral.
Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.
Trail half marathon and 5 mile at Brookhaven State Park on Nov 15, 2026, on single track and fire trails with awards, cash prizes, and finisher medals.
Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.
Trail races at YMCA Camp Sloper on November 21, 2026, offering a 400 minute loop challenge and a four mile option with chip timing and an aid station.