Millbrook
Trail Running Calendar near Millbrook 2026-2027
Explore the top trail runs near Millbrook for 2026-2027! We've gathered 17 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
October 2026
Multi day endurance series at Mohawk Mountain Ski Area offering timed lap events from 15 to 152.5 miles with individual and team flex relay options.
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.
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.
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 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 5k and 1.5 mile walk at Millbrook Vineyards & Winery on May 15, 2027, featuring a mostly grass cross country course and a post run wine pour.
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.