Norwalk
Trail Running Calendar near Norwalk 2026-2027
Explore the top trail runs near Norwalk for 2026-2027! We've gathered 41 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
Trail race at Westmoreland Sanctuary covering about 6.5 miles of rocky, rooty trails with parking at Fox Lane Middle School, awards by age group, and no dogs allowed.
September 2026
A family friendly, obstacle filled beach 5k in Stratford that raises funds for Sterling Community Center while supporting individual and team fundraising.
Trail ultrarace in Upper Nyack, NY with a 50 mile and a 27 mile course featuring roughly 9,700 and 4,900 feet of elevation gain.
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 six-hour timed run and relay at Belmont Lake State Park where individuals and teams cover as many 1.50 mile loops as possible, with awards and commemorative apparel.
October 2026
A 30 hours looped trail ultra in Roosevelt Forest CT with multiple distance options, a 2.5 mile loop, single pavilion aid station, pacer rules, and finisher buckles at 100 miles.
A 4-mile trail race through Irvington Woods on October 4, 2026, starting and finishing at the Irvington High School campus; rain or shine.
Multi-day trail event in Rocky Point NY on a 10.48 mile loop used for distances from 10 to 150 miles, with two aid stations and crew support.
A fall trail event at private Gemstone Farm in Wilton CT with a timed 3.1 mile race, an accessible short run or walk, live music and farm access.
A scenic 5K through the carriage roads of Rockefeller State Park Preserve with hilly terrain, Swan Lake views, awards, t shirts and proceeds supporting carriage road maintenance.
A trail half marathon in New Rochelle that loops through five Westchester County parks and runs mostly on dirt trails shaded by woodland canopy.
Trail 5K and free kiddie dash at Blydenburgh County Park on October 11, 2026 with a virtual option, finisher tee, shaded trails, and postrace refreshments.
Experience Long Islands scenic Robert Moses Causeway in this multi day running event. Support local veterans while choosing between marathon, half marathon, 10k, and 5k distances with finisher medals for all participants.
Trail event at Muscoot Farm in Katonah on October 25, 2026 featuring a 5 mile race and two kids races, with Farm Bucks and kids medals.
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.
Trail events at Ward Pound Ridge Reservation: a 10k trail race on November 8, 2026 and a month long Raven 100k Challenge with wooden finisher medallions.
A community 5K at Belmont Lake State Park on November 8, 2026 with in-person and virtual options, family activities, postrace refreshments, and proceeds supporting the Never Stop Running Foundation.
Championship cross-country 8K at Bethpage State Park on November 8, 2026, for Open, Masters and Para Athletic categories with age-group and team awards.
A family-friendly trail 5K at Bethpage State Park on November 14, 2026, offering in-person and virtual options, refreshments, finisher photos, and a free kids dash.