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Foggy,
If you have a car, the Mohonk Trail in New Paltz is a great place to ruck with tons of trails. If you want some sand to challenge you, the Pine Barrens in South Jersey has thousands of miles of trails, literally. Also, the Greenbelt on Staten Island, where you will likely run into other people doing the same thing. If you are looking for some decent hills, the Greenbelt is probably your best bet. Another place worth trying is Prospect Park in Brooklyn, some great trails there and even a few good hills.
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