Millbrook
Trail Running Calendar near Millbrook 2026-2027
Explore the top trail runs near Millbrook for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail races at Red Wing Recreation Area Oct 31 to Nov 1 2026 offering 100k, 50k and 10k looped courses with aid stations and finisher medals.
A Halloween trail event in Rosendale with a timed 5k, a 2k walk and a free 1k kids run at Fifth Lake Hudson Valley.
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 100 percent cross country 5K at White Memorial Foundation & Conservation Center in Litchfield with natural trail footing, a midcourse hill, on-site outhouses, and Sawmill Field parking.
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 memorial 5K run and walk on the cross country course in Danbury offering a chance for friends, family and teammates to gather and remember.
A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.
May 2027
A technical trail race in Beacon NY with a half and full marathon featuring heavy elevation gain, exposed climbs, aid stations, and strict aid station support rules.
A chip timed 5K at Brooklyn Cider House on May 22, 2027 combining a run or walk with local cider, a shirt, medal, donut and a pour of cider.
June 2027
July 2027
A roughly 5 miles trail run through varied terrain at Bowdoin Park in Wappingers Falls, with a 150 runner cap and awards for overall top finishers.
September 2027