The Chester Challenge
Designed by the Town of Chester in Warren County, the Chester Challenge encourages hikers to explore the town's expansive regional trail network. The Chester Challenge is a more family-friendly hiking challenge, and it was created to appeal to people of all skill levels.
To complete this hiking challenge and receive a commemorative pin, all you have to do is complete 6 out of 11 designated trails.
The Chester Challenge was funded by state grant money awarded to the Town of Chester by Glens Falls Hospital's Health Promotion Center. Not only does the challenge help to promote physical fitness and wellness, but it's a great way to explore some of the lesser known trails in the Town of Chester area.
One of the most interesting aspects of the Chester Challenge is that you don't have to complete all of the challenge's designated trails. Instead, there are a few different options depending on how hard you want the challenge to be. For example, you can hike the longest and more challenging trails and receive a special pin, or you can choose the easiest and still get the pin. It's up to you to decide!
Basically, there are 11 trails in total and 8 locations to choose from. Some of those 8 locations include two trails, one easy and one hard. Once you hike any 6 of those trails, all you have to do is report in to the town clerk's office in Chester, the Dynamite Hill Visitor Center, or the Crossroads Store, and then you'll receive a commemorative challenge pin. Or, if you complete the challenge in winter, from December 20th-March 20th, you will receive a special patch.
The 8 Locations
- At Green Hill and Catamount Mountain, Chester Creek Trails, and Cougar Nature Trails, you can choose between taking a shorter route or a longer route.
- All of the distances/times below are round-trip.
1. Stewart Mountain
This easy dirt trail is a very short hike up to the top of Stewart Mountain. There is one steep section to be aware of on the way back down.
Distance/Time: .8 mile/45 minutes
Access/Parking: From Northway Exit 25, head west on Route 8 for about 4.4 miles. When you reach White Schoolhouse Road, follow it for 1 mile to reach the parking area and trailhead.
2. Cougar Nature Trails
There are two ways you can tackle the trails at Cougar Hill. The first is a short, more direct trail up to the top of Cougar Hill, and the second is a long and gradual trail.
Distance/Time: .9 mile or 4.5 miles/1 to 2 hours
Access/Parking: You can park in the North Warren Central School parking lot by the tennis courts or visitor parking area (6110 NY-8, Chestertown, NY). Check in with the school guard during regular school hours. The trailhead will be a short walk away.
3. Palmer Pond Trail
This dirt trail is great for beginners because it is relatively flat and offers scenic views of the surrounding wildlife. The trail itself is a short loop around the 31-acre Palmer Pond.
Distance/Time: 1.5 miles/1 hour
Access/Parking: From Northway Exit 25, head west on Route 8 for about 6.7 miles. When you reach Palmer Pond Road, follow it to the end where there is a parking lot and trailhead.
4. Chester Creek Trails
Take a walk around the wetlands areas of the Chester Creek Trails, located just behind the Town of Chester Municipal Center. The trails are mostly flat, and you'll see a lot of flora and fauna along the way! Walk all of the trails for a slightly longer hike, or just take a short stroll.
Distance/Time: 1.2 miles or 1.9 miles/45 minutes to 1 hour
Access/Parking: From the center of Chestertown, visit the Town of Chester Municipal Center on the west side of Main Street. Park in the Municipal Center's north parking lot, and then head to the trailhead behind the building.
5. Kipp Mountain
The dirt trail up Kipp Mountain is rated as moderate because it has some steep sections along the way. The trail travels through an actual tree farm, and at the top, there will be great views overlooking Loon Lake.
Distance/Time: 1.9 miles/2 hours
Access/Parking: From Northway Exit 25, head west on Route 8 for about 1.6 miles to Landon Hill Road. Follow Landon Hill Road for 2.9 miles to Ben Culver Road. The parking area will be located about 1 mile down Ben Culver Road.
6. Meade Mountain and Beckman Mountain
This location is one of the longer options for the Chester Challenge. The trail begins at the Meade Mountain trailhead, and the trail ends with a view of Gore Mountain. Then, there will be a short descent followed by an ascent up Beckman Mountain, which provides a view of Loon Lake. Some of the sections are long and steep.
Distance/Time: 2.1 miles/2.5 hours
Access/Parking: From the center of Chestertown, follow Route 9 west, and then follow Route 9 north as it passes by Loon Lake. Just past the lake, you'll reach Igerna Road. Follow it for .75 mile and you'll see the designated parking area for this trail.
7. Dynamite Hill and Caroline M. Fish Memorial Trails
Dynamite Hill is open for many forms of recreation throughout the year. The trail system is 2.6 miles long, and it connects to the Caroline M. Fish Memorial Trails.
Distance/Time: 2.6 miles/1 hour
Access/Parking: One parking area is between Exit 25 and Chestertown, and it will be on Route 8. The second parking area is a short ways up Landon Hill Road, which is north of Chestertown and at the intersection of Route 8 and Main Street.
8. Green Hill and Catamount Mountain
From the Stone Bridge and Caves attraction in Pottersville, you can access Green Hill and Catamount Mountain. Green Hill is a moderately steep hike, and Catamount Mountain is a much more challenging hike.
Distance/Time: 1.8 miles or 6.4 miles/1 hour to 4 hours
Access/Parking: These hikes are available at the Stone Bridge and Caves attraction, and they are open as a guided hike in the summer or a self-guided snowshoe hike in the winter. Be sure to check hours and pricing ahead of time.
For more information about the Chester Challenge, call the Town of Chester's town clerk's office at 518-494-5160.
Photo: Palmer Pond by Sara Westcott