Monticello
Walking Events Calendar near Monticello 2026-2027
Monthly updates for Monticello
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Explore the top walking events near Monticello for 2026-2027! We've gathered 12 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
Walkers can take part in a 5K walk from the Delaware Youth Center in Callicoon along a fast flat course beside the Delaware River with scenic river views. There are overall awards for walkers and the event runs alongside the running races.
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 can join routes at Belleayre Resort in the Catskills on the 25K or 8K. The 25K is about 16 miles with 5000+ ft of climbing on difficult terrain, while the 8K is on ski slopes; course maps are provided for hikers.
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 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 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 can use the marked 3.1 Miles trail at Van Scott Nature Reserve of the Delaware Highlands Conservancy on wooded, unpaved trails and should bring baby and hiking carriers as routes are not stroller friendly. Water stations and first aid are..