Chester
Walking Events Calendar near Chester 2026-2027
Monthly updates for Chester
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Explore the top walking events near Chester for 2026-2027! We've gathered 39 great walks in the area. Check out our detailed list below to find your next local walk.
October 2026
The Zombie Crawl includes a 1 Miles walk on Clinton Road in West Milford NJ through shadowy woods and foggy stretches; check in is at the corner of Van Orden Rd and Clinton Road and watering stations are on course.
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.
The event includes a 6.2 Miles 10k Walk in Port Jervis starting at 10 Route 209 on a city course that showcases peak fall foliage and the new school athletic facility. The route runs alongside the running races for a scenic community walk.
The event offers a 5K walk at Orange County Airport in Montgomery, NY along a flat airport course. Walkers will not be timed and packet pick up includes light refreshments.
Walkers are welcome on the 1/2 Marathon and 5K starting at Philipstown Recreation Department in Garrison NY, on Hudson Highlands single and double track trails with river views; 5K has no cut off.
Walkers can take the 5K course starting at 5 Van Wyck Lane in Wappingers Falls, NY. A 1K kids fun run runs alongside the running races and proceeds benefit Blood Cancer United.
November 2026
Walkers can choose 26.2 Miles or 13.1 Miles routes that start and finish at Rockwood Hall in the Rockefeller State Preserve. Routes follow wide groomed carriage roads and trails with no pavement or cars, pass rivers, forests and stone walls,..
The event offers a 5K (3.1 miles) walk at Sussex County Fairgrounds in Augusta NJ on an accessible course with water stations, parking and running buddies for support.
Walkers can take the 5K course through River Vale's picturesque streets, starting at Mark Lane Sports Complex. The family friendly route welcomes strollers and walkers of all ages alongside the running races and supports a local food pantry.
Walkers can use the flat 5K course at Greenview Park in Pequannock NJ, running through the town center. The event welcomes walkers and families and offers custom bibs and T shirts for the first 200 participants.
Walkers follow the 5K route from 68 Sandhill Rd, Sussex NJ, on a rural course with hills, turns and a cheering section of local cows. Registration includes group pricing and children under 10 walk free.
December 2026
Walkers follow a 4 miles course in Middletown at the Middletown Elks Lodge near the YMCA, with a mile two hill, a water stop, awards for top walkers and food after the race.
February 2027
Walkers can do the 1.6 miles loop or the full 5K from NYNJTC Headquarters on a flat, scenic gravel and dirt loop around Scarlet Oak Pond; aid station, no cutoff.
May 2027
Walkers can choose 1 Mile, 5K, 10K, Half Marathon or Marathon routes across the historic Walkway Over the Hudson in the scenic Hudson Valley.
Walk options 5K, 10K, 15K on looped course at Rockland Lake State Park Parking Lot #2, with start and finish at the same location alongside the running races.
June 2027
At Rockland Lake State Park, walkers can choose a flat, accessible 5K lake loop or a rugged 10K to Hook Mountain. The 5K is accessible with restrooms; the 10K is technical, 1,300 ft with cliffs and one aid station, no crew.