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:
- Green Hill and Catamount Mountain - Climb either a steep, 1.8-mile trail to a beautiful view or a challenging, 6.4-mile hike to views of the distant Adirondack High Peaks. These hikes are only available through Natural Stone Bridge and Caves and do require a fee.
- Meade Mountain and Beckman Mountain - A steep, 2.1-mile hike with views of Loon Lake, Gore Mountain, and Blythewood Island. Hikers will summit two separate mountains on this moderate trail. Read the Hiking Highlight!
- Kipp Mountain - This easy-to-moderate, 1.92-mile climb brings hikers to a ridge with gorgeous views of Loon Lake below. Read the Hiking Highlight!
- Stewart Mountain - An easy, 0.84-mile hike with one steep section and close-up views of Loon Lake. Read the Hiking Highlight!
- Chester Creek Hiking Trails - These 1.2-mile to 1.9-mile trails are mostly flat, leading up to Chester Creek and its surrounding forest and wetlands.
- Dynamite Hill and Caroline M. Fish Memorial Trails - A 2.6-mile path connects Dynamite Hill through the woods to the Caroline M. Fish Memorial Trails. Dynamite Hill also offers skiing/snowboarding, tubing/sledding, cross-country skiing, snowshoeing, and ice skating in the winter.
- Palmer Pond Trail - Go fishing or see wildlife on this 1.5-mile New York State hiking trail. Stop and marvel at the wonderful views along Palmer Pond.
- Cougar Nature Trails - A steep trail or a more gradual trail brings hikers to the top of Cougar Hill. Additional nature trails bring hikers through forest and fields around Cougar Hill.
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.
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