Middletown
Walking Events Calendar near Middletown 2026-2027
Monthly updates for Middletown
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Explore the top walking events near Middletown for 2026-2027! We've gathered 24 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 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 with COLOR BLAST stations on the course plus vendor areas and a memorial marker display.
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.
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.
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.
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.