Billings
Trail Running Calendar near Billings 2026-2027
Explore the top trail runs near Billings for 2026-2027! We've gathered 31 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Test your endurance at the Pawling 24 Hour Trail Running Festival featuring multiple timed races on a scenic 1.68 mile loop in Lakeside Park.
October 2026
A veteran-run series of elevation-based mountain endurance events at Mohawk Mountain CT and Amicalola Falls GA, offering seven solo and team formats from 12 to 84 hours.
Experience 13.7 miles of Hudson Highlands trails with 4000 feet of elevation gain during the peak foliage season in Cold Spring New York
Experience a trail run through Mohawk Mountain Ski Area and Mohawk State Forest featuring steep climbs and scenic fall foliage across distances from 5 km to a full marathon.
Pickle themed Halloween obstacle event at Obstacle Wonderland in Wallkill NY with adult 5K, kids 1K, a pumpkin carry fundraiser, themed medals, and family friendly activities.
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.
A community half marathon, 5K and kids fun run in Garrison, NY, with trails through Hudson Highlands and proceeds benefiting local recreation programs.
Test your endurance at Red Wing Recreation Area with a series of looped trail races ranging from 10k to 100k featuring significant elevation gain and constant support.
A Halloween trail event at Fifth Lake Hudson Valley with a timed 5K, a 2K walk and a free 1K kids run, featuring themed medals and spooky course elements.
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.
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.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
A community 5K and a 1-mile kids run at Sargent Elementary in Beacon, NY, with a food drive, live DJ, and refreshments.
A farm based 5K trail run plus a kids fun run for ages 6 and under in Yorktown Heights supporting Friends of Hilltop Hanover Farm.
Trail half marathon at Minnewaska State Park Preserve around two glacial lakes and along the Shawangunk Ridge; online registration, $30 fee, 300 runner cap.