Bear Mountain
Trail Running Calendar near Bear Mountain 2026-2027
Explore the top trail runs near Bear Mountain for 2026-2027! We've gathered 38 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
Multi-distance trail festival at Ringwood State Park Sept 18–20 2026 with looped courses, a central aid station, and options from a kids mile to 100 miles.
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 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.
Trail run at Jungle Habitat in West Milford NJ with Half Marathon plus, 10K plus and 5K plus loops on a USATF sanctioned course featuring single track and fire road.
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.
Pickle-themed Halloween obstacle event in Wallkill, NY with a 5K adult course and 1K kids race, costumes, handmade medals, and a community donation drive.
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 technical trail half marathon and 10K through Harriman State Park near Tuxedo NY, featuring steep climbs, rock fields, and significant elevation gain.
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.
Tri-State New York Spartan Weekend in New Hampton, NY, Oct 31 to Nov 1, 2026 features Sprint and Super obstacle races, kids events, workshops and Hurricane Heat formats.
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
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.
Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.