Experience the Town of Chester's surrounding peaks and waterways!

The Chester Challenge hikes consist of trails within the Town of Chester. Trails range from easy to moderate and include steep hikes as well as walks in the woods. Visit six trails and receive the Chester Challenge pin. Hikers up for a real challenge will receive a special Winter Challenge pin or patch after they hike, cross-country ski, or snowshoe at least part of at least six trails between December and March.

Brochure maps available at Town of Chester Municipal Center and North Warren Chamber of Commerce, or online.

Hike six of these trails to complete the Chester Challenge:

Note: When you have completed your Chester Challenge hikes, stop in and see the Town Clerk in Chestertown to register your finish and get your pin! 6307 State Route 9, Chestertown. Check the town website for office hours.