Chester Challenge

Town of Chester Municipal Center,
6307 State Route 9
Chestertown, NY 12817
518-494-2711; 518-494-2722
You can enjoy…
Eastern Adirondacks
Cross Country Skiing
within Adirondack Park
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Hike the Chester Challenge and experience the Town of Chester's surrounding peaks, waterways and nature.

The Chester Challenge hikes consist of trails of various levels of difficulty and variety of terrain within the Town of Chester. The 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, 518-494-2711 and North Warren Chamber of Commerce, 518-494-2722 or online.

To complete the Chester Challange - hike six of these trails:

  • 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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DEC Lands, Trails and Points of Interest Disclaimer New York State
Department of Environmental Conservation (NYS DEC) distributes this geographic data with the understanding that geographic data, including land boundaries as represented, are approximate, and are intended for broad scale planning, inventory, mapping and analysis activities. No survey level accuracy is conveyed. No proof of land ownership is represented. NYS DEC makes no guarantee or warranty concerning the accuracy of information contained in the geographic data. In order to improve data quality, the user is asked to document discovery of errors to the Division of Lands and Forests in writing. Lands data should be used for general information purposes and not to determine property boundaries. In many instances, the state lands and other data layers do not align precisely with the aerial photography. Certain trails and points of interest which may exist on the ground are not currently displayed in this mapper. These datasets are works in progress and will continually be improved.
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