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There are some interesting hikes starting from the Reeves Meadow visitor center on Seven Lakes Drive. The area south of the visitor center is pretty dense with trails, so you have a lot of options.
The primary advice that I will give is to stay away from plant fibers -- they absorb sweat and keep you cold. Nothing that you wear, with the possible exception of a bandana or baseball cap, should be
I've broken trail about 10 times over the past 10 years. The thing is, unless you go out the day after it snows, you're not likely to be the one breaking trail. Generally, what you want to do is plan
I enjoy winter hiking, and have been using some variety of specialized footwear for the past several years. If there is more than a few inches of snow on the ground, then I hike with snowshoes or spikes
The hike that you are describing is moderately difficult. You'll have a fairly challenging climb at the start, starting right after you cross the Palisades Parkway, plus a couple of slightly less strenuous

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