Explore the most popular trails near Chester with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

Chester, New York Map
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We encountered a black bear on this trail. Luckily, you have pretty good visibility of what’s ahead so we saw him and we were able to turn around and walk briskly back to the trailhead. Pretty walk through the woods to see some changing leaves. It’s mostly flat just a short hill in the beginning.

This trail is listed at moderate I would consider it as being easy. Overall great trail

Definitely not moderate. Easy walk on a gravel path.

So we parked at the designated parking area on 17 and entered the trail from there (multiple trails) we walked in about 1.5 miles on a half paved road. It was nice & serene easy easy walk

hiking
bugs
over grown
3 months ago

hiking
over grown
3 months ago

I am a new hiker. I hate out and back. I could not find the loop. Saw a few trails in the right direction but I was uncertain. If the trails had been marked, I would have given it a shot. I think I saw 2 trail markers in 2 miles. As it was, I walked a once paved road out and back. Beautiful and well shaded. I would do it again. Maybe in spring when the grasses aren’t so high. The trailhead is across the street from the parking lot.

hiking
blowdown
bugs
over grown
4 months ago

This is a relatively easy hike with few views. We saw a few deer on the hike which was the highlight. The trail is very overgrown yet still easy to follow. There are no Trail markers so depending on the time of year you could get in trouble if you don't know where you're going. Being that it was in the middle of the summer it was easy to follow the slight footpath that exists. I would not want to try and follow this Trail in the fall or spring. Overall if you were looking for a quick hike that will get your heart rate up this is definitely it. Just don't be expecting to see much in views Department.

mountain biking
bugs
over grown
rocky
4 months ago

I enjoyed it for my first time biking in a few years. A good amount of uphill riding with some fun downhill areas (I started on the Rt 17 side). I rode Lazy Hill Rd. There are a bunch of side trails and 2 old cemeteries as well - which I didn’t get a chance to explore yet. Some of the road is old pavement and some not paved. Enjoy!

Really easy leisurely walk. Smells really fresh this time of year (June 1). Would be great for an easy refreshing bike ride. Definitely will return for that. Great leashes dog walking trail too, and people actually follow that rule.

hiking
blowdown
bugs
muddy
scramble
5 months ago

love this place been riding it for about 4 yrs takes few times to figure it out but is fun when you , goes from easy on the chester side to real techy on the monroe. next time i ride it I'll strava it can get maps at Joe's fix it in goshen

hiking
muddy
7 months ago

found it base on your review, Thanks Paul. It does have green blazes that are very widely spaced then they become old faded white blazes, but for the most part the trail is easy to follow as it makes it way over the top towards a view of rt 17 at this time of year. You need not worry about getting seriously lost as the trail does skirt along the back yards or within view of homes along the way. If you'd like to do some addtional expolring there go to "find a grave" type in chester cemeties and then " Board famliy" and " Davis family" with the GPS lat/long you can a find the little cemetieses but you need boots for the Board cemeatry ankle deep water around the little hill .

First of all, what is highlighted on this page on the map and the elevation profile are NOT Goosepond Mountain Trail, they are of Lazy Hill Road. Goosepond Mountain Trail goes to the west of Lazy Hill Road and actually goes up and over Goosepond Mtn. If you approach the mtn from the south, at the Laroe Rd trailhead, proceed along Lazy Hill Road, which is a old road. After about a half mile, just as you approach a stream, there is a faint trail on the left, which is accessed by crossing the stream. It is then not too hard to follow the trail up to the top of the mountain. It rolls for a while and then climbs more steadily. At times it is blazed. At times it follows old woods road grades. I only went as far as the top of the mtn, and then went back to the trail head. It was a total of just under 4.5 miles round trip according to my phone GPS.

mountain biking
11 months ago

nice trails easily marked .

It was a peaceful hike along this primarily flat terrain. Beautiful view of the mountains and fall foliage.

hiking
Sun Oct 14 2018

Nice walk through the woods. Little tame one or two nice view spots. Dog loved it - very pretty foliage. Would rate as easy and the trail markers could a little better.

hiking
Sat Oct 06 2018

Not too exiting the first 2 miles on main trail, once off the trail you will need a machete. Hi grass and thorn bushes, that part of the trail is not maintained and completely grown over. Maybe good for a winter hike?

A nice trail for a hike. Definitely going back to do another loop!

mountain biking
Sun Jul 08 2018

Started at the 17m entrance across the road from the parking lot. There's an initial climb, but nothing too intense. It transitioned from gravel to blacktop, so it's pretty easy riding. I noticed trails that offshoot from the main path and I ventured off on one that was fun to ride, but ended running into a tall grass open field. Lots of thorny plants too so gloves were helpful, pants would have been nice too. Got back onto the main path and followed to the end at Laroe Rd. On the way back found a trail that went right, up the hill (had to push it) and eventually up to the top. There was a wide path through grass and woods that takes you under the power lines. I turned around and headed back which was all downhill and lots of fun. Followed a different trail that cut across and eventually popped out on the main path. Definitely recommend making the climb up that trail, if you're looking for something more challenging and fun. On a Sunday I did encounter 4 or 5 others, some with dogs, and there was a group of 4 on bikes.

It was ok but not much to see in mid April

I knocked off a star because I almost got run over by a dirt bike, but this is a terrific place for a walk with kids or a nice trail run. Mostly flat with lots rolling hills and meadows, or you can walk along the flat dirt road with a sturdy jogging stroller.

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