Chester
Walking Events Calendar near Chester 2026-2027
Monthly updates for Chester
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Chester for 2026-2027! We've gathered 36 great walks in the area. Check out our detailed list below to find your next local walk.
August 2026
The event offers a 5K walk starting at Resorts World Catskills in Monticello, NY on a scenic and challenging road course through the Catskills. The walk takes place alongside the running races and welcomes all ages and ability levels.
The walk is a 4 Miles course starting at Run 4 Downtown Park, 15 North Street, Middletown, NY. The route goes through historic downtown alongside the 4 Mile run and follows the event's gender based start order.
Walkers follow a 3.1 Miles route through Thomas Bull Park in Montgomery NY alongside running participants. The park course supports mental health fundraising for local services.
September 2026
Walkers follow a 2 Miles route from downtown Ossining on Main Street north along the scenic Old Croton Aqueduct Trail, alongside the 5K, with a $35 registration fee.
Walkers follow a 3.1 Miles hybrid course from Hershfield Park in Pompton Lakes, NJ, crossing fields, trails, roads and a pipeline path. The course is well marked with marshals and a single water stop at the course center; same day registration ru..
Walk the 5K course at FDR State Park Lot 1, 2957 Crompond Road in Yorktown Heights in a park setting alongside the running races. Race day registration is available and festivities include vendors, food trucks, live music and pet adoptions.
Walkers can choose the 5K through scenic Cold Spring and Nelsonville or a 0.3 miles Family Fun Run on the lower blocks. The event is based at Cold Spring Riverfront Bandstand; walk up registration, free parking at Metro North Station.
Walkers can choose the 5K route beginning at Memorial Park, 2 Robert Cahill Dr in Beacon. The course is relatively flat but includes a hill near the start, and a virtual 5K option is available.
Walkers follow a 3.10686 Miles route that starts on the baseball field track at Mount Saint Mary College Campus in Newburgh, NY, loops twice through campus with Hudson River views; pre registration is $25.
Walkers follow a 5K route at the New Jersey State Fairgrounds in Augusta NJ, listed also as 3.1 miles. The course includes several COLOR BLAST stations and memorial markers on the route for those who raise $150, with vendors and a memory wall..
Walkers can choose a 5K out and back on the scenic, flat D&H Canal Tow Path starting at the Mamakating First Aid and Rescue Squad in Wurtsboro, NY. Race day registration is available on the morning of the event and all registrations are final and..
October 2026
Walkers can take a 5K course through Thomas Bull Memorial Park in Campbell Hall NY, a family friendly park with playgrounds and park scenery. Race day registration is available for $40 cash only and the event runs alongside a 10K run.
The 5k walk is family friendly, covers 3.1 Miles, is not timed, and starts at 1018 Westwood Ave in Old Tappan NJ.
Walkers can join the 5K course at PCCC Wanaque Academic Center in Wanaque, NJ, with in-person and virtual options alongside the running races. Day of registration opens at 7:00 a.m.
Walkers can join the 5K in person at Croton Harmon High School, 36 Old Post Road South, then move up to Five Corners to line up for the start. A virtual 5K (3.1 Miles) is available between Oct 10 and 17, and the first 300 5K registrants g..
Walkers follow a 3.1 Miles Run/Walk course at Rockland Lake State Park, starting via the North Entrance near parking lot 1. Strollers are welcome, the park charges a $10 vehicle entrance fee and registration is online only.