Weston
Walking Events Calendar near Weston 2026-2027
Monthly updates for Weston
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Weston for 2026-2027! We've gathered 88 great walks in the area. Check out our detailed list below to find your next local walk.
November 2026
At Tarrywile Park in Danbury walkers can choose 10K, Half Marathon, or Marathon on a looped, technical single track with close to 3K elevation and lakes and viewpoints. Aid stations are on course but walkers must carry their own cup or bo..
Walkers are welcome on the 13.1 miles trail at Roosevelt Forest, 700 Peters Lane, Stratford CT, consisting of eight 1.64 mile wooded loops on marked singletrack and doubletrack with roots, rocks and rolling hills. Aid station and porta potties ar..
Walkers can choose 10 km or 5 km routes at Westchester Community College in Valhalla, NY, with an untimed 5 km option alongside the running races. Both in person and virtual options are offered.
The event offers a 5K road loop that starts at Bethel Municipal Center in downtown Bethel and goes through the town neighborhoods. The course is moderately uphill in the first half and downhill in the second half, with the first and last one thir..
Walkers can complete the 5K course starting at 575 Vanderbilt Parkway, Dix Hills, NY 11746, with on site parking and extra nearby parking. Water, bathrooms and free finish line photos are provided, and walkers can get a personalized bib if regist..
December 2026
Walkers can complete the 5K out and back course starting at 10 Washington Parkway in Stratford along a flat scenic waterfront in the Lordship section. The family friendly route suits all abilities and collects new, unwrapped toy donations at bib..
Walkers can complete the 5K on forest trails at Roosevelt Forest, 700 Peters Lane, Stratford CT, following an off road wooded route that requires a little trail experience. The pavilion is the sole aid station; parking is limited and larger vehic..
January 2027
March 2027
Walkers can choose 5 km or a 1 mile family walk from Smithtown Elementary School in Smithtown. The relatively flat course runs through residential streets with police control, water stops and mile splits, and bib pickup is available before an..
April 2027
The 4k Jay Walk offers a 4 km non competitive route starting at the John Jay Middle School field that follows the wooded John Jay Community Trail. It skips the first out and back loop, starts after the 5k runners enter the woods, and finishes at..
Walkers can choose 5K, 10K, or a 4 hour option on the 3.2 mile loop at Lake Mohegan, Fairfield CT. Trails are runnable and varied. Water at start finish for 4 hour and 10K; no on course aid for 5K and event is cupless.
May 2027
Walkers can follow the 5K course starting at The Mary Louis Academy in Queens, with a mapped route available online. Amenities for walkers include free finish line photos, live, text and email results, and in person or virtual bib pickup with per..
Walkers can join the 5K at Glen Cove High School, 150 Dosoris Lane, Glen Cove NY, on a mapped course alongside the running races. Pre race and day of bib pickup are available at the YMCA and at the high school, with post race refreshments and fir..