Norwalk
Trail Running Calendar near Norwalk 2026-2027
Explore the top trail runs near Norwalk for 2026-2027! We've gathered 46 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.
Experience a challenging 50 mile or marathon trail race featuring 9600 feet of elevation gain and scenic Hudson River views at Hook Mountain.
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 on a 2.50 mile loop, with individual and team entries, post-event food, awards, and charity support.
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.
Four miles of trail running through the Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus on October 4, 2026.
Four-day trail event in Rocky Point, NY featuring a 10.48-mile Pine Barrens loop with eight distance options from 10 miles to 150 miles.
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.
Scenic 5K at Rockefeller State Park Preserve featuring hilly carriage roads, age group and team awards, t shirts and refreshments, with 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 at Blydenburgh County Park on October 11, 2026 offering in person and virtual options, participant tees, refreshments, and age group recognition.
Multi day running weekend in Bay Shore, NY with marathon, half marathon, 10K, 5K, kids 1K, relay and a virtual 26.2 miles challenge.
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
Experience a community-focused trail race featuring a 4 mile loop of rolling farm trails and single track with timed options, a 4 mile distance, and a 5K Canicross.
A community 5K and untimed fun run at Sachem North High School on November 7, 2026, offering awards, free finish photos, and guaranteed shirts for early 5K registrants.
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 offering an in-person 5K, virtual option, and a free kiddie dash with post-race refreshments.
An 8K USATF cross-country championship for Open, Masters and Para Athletic divisions at Bethpage State Park on November 8, 2026, for athletes aged 18 and older.