Cross River
Trail Running Calendar near Cross River 2026-2027
Explore the top trail runs near Cross River for 2026-2027! We've gathered 35 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.
Timed trail event in Pawling, NY with 3, 6, 12, and 24 hour races on an about 1.68 mile loop, aid station, crew area, and finisher medals.
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.
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.
A trail half marathon in Cold Spring NY covering 13.7 miles with 4,000 ft of climb through the Hudson Highlands while supporting the NYNJTC.
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.
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.
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.
Trail half marathon, 5K and a 3/4 mile kids run in Garrison NY, fundraising for The Friends of Philipstown Recreation with a course that passes Osborn Castle.
A multi-day trail running event at Red Wing Recreation Area near Lagrangeville, NY offering 100k, 50k and 10k looped courses with aid, medals and UTMB Index status.
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.
A trail event at Ward Pound Ridge Reservation featuring a 10 km race, a November 100 km virtual challenge, rugged climbs, and fundraising for the Friends of Trailside Museum.
Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.
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.