5K races near Kingston

Kingston Base Miles

Kingston hosts 37 5K races in 2026 within 80 km of the city centre — upcoming dates, recurring series, and other races nearby, all in one place.

The route runs 5 miles through town with off-road paths and on-road sections. The off-road stretch runs 5 miles from North Street to John Street. Onteora Runners Club keeps the race calendar honest with the ORC Grand Prix Woodstock Races 15k in Kingston, plus Ashokan Rail Trail 8 Miler and Rosendale Runs Half and 6k. Capital to Capital 5k works as a local anchor event.

Kingston riders get mixed-terrain days fast, especially when the route points toward the Wallkill Valley Rail Trail. The trail runs 7 miles from Amy Kay Pkwy to Boulevard Ct, and locals use it for Z2, gravel bike miles, and from tip to tail efforts. Cycle Club Kingston gives the scene a real club spine with summer group rides and winter indoor training. Hudson Valley's 21st Annual Tour de Kingston and Ulster, Dirty Dutchess 2026, and Cabin Challenge sit on the calendar. The Shawangunk Ridge and Dirty Dutchess terrain bring the climbing, with grand estates, horse farms, hidden lakes, and the Omega Institute in the mix.

Summer is the clean pick for Kingston because Cycle Club Kingston led outdoor group rides during the summer months and runners can stack base miles on the rail-trail pieces. The loop runs 13 km and gains 185 m. Winter changes the rhythm without killing it. Cycle Club Kingston held indoor training from November through March, and runners lean harder on paved trail sections, shorter routes, intervals, and steady Z2 when the weather turns.