Ridgefield
Trail Running Calendar near Ridgefield 2026-2027
Explore the top trail runs near Ridgefield for 2026-2027! We've gathered 34 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A forested 5K on August 9, 2026 at Bridgewater Town Park featuring new trails, modest hills, participation gifts, and prizes for top finishers.
Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.
Trail races in Fahnestock State Park near Cold Spring NY offering 50K, 25K and 5.5 mile options with on-course aid and a post-race meal.
On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are collected.
September 2026
An obstacle-based 5K at Short Beach, Stratford on September 12, 2026, with 18+ obstacles and fundraising for the Sterling Community Center.
Timed trail races in Pawling NY offering 24, 12, 6 and 3 hour options on an approximately 1.68 mile loop with on course aid and athlete camping.
A USATF-sanctioned trail event in Upper Nyack with a 50 mile option featuring four 11.5 mile loops, about 9,700 feet gain, and three aid stations.
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.
October 2026
A 30-hour trail ultra at Roosevelt Forest in Stratford CT with 2.5-mile loops, buckles at 100 miles, and a 50 participant field limit.
A 4-mile trail race through Irvington Woods on October 4, 2026, starting and finishing at the Irvington High School campus; rain or shine.
Trail half-marathon in Cold Spring NY on October 4, 2026 featuring 13.7 miles and 4,000 ft of gain through the Hudson Highlands; proceeds support NYNJTC.
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 single-loop trail half marathon through five parks in lower Westchester County, New Rochelle. Most of the course is on dirt and wooded trails and passes through areas with visible wildlife.
HHNC Meadows & Trails 5K is an off road 5K at Hudson Highlands Nature Center in Cornwall NY on 10/17/2026, featuring meadows, ponds, wooded trails and views of Black Rock Mountain. Entry is $35 and children under 18 run free.
A trail event at Muscoot Farm on October 25, 2026: a five-mile race plus two kids races, kids medals, and Farm Bucks for finishers.
Half marathon and 5K in Garrison NY through Hudson Highlands and past Osborn Castle with proceeds supporting Friends of Philipstown Recreation.
Looped trail races at Red Wing Recreation Area in Lagrangeville, NY offering 100k, 50k, and 10k courses with aid stations and finisher medals.
November 2026
Timed trail event at Gurski Farm in Brookfield CT featuring an 8 hour race, a 4 hour option, and a 5K canicross on a 4 mile loop.