angeloboot Offline Upload & Sell: Off
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I'd start exploring town lands/county greenbelts and google maps. I'm around the 93/95 interchange, so I either go west out towards Assabet or northeast up 95. There's lots of smaller parcels that exist as either town-owned or part of a conservation group's easement, etc, but it takes me a lot of online homework in advance to be sure I'm not trespassing. One thing that works for me is to look for railbeds on google maps, and then figure out which ones are no longer/rarely in service. Often the railbeds go through marshes/forest etc, and then it's just a matter of viewing town platt/assessor's maps to see where you can walk.
Unlike where I'm originally from (Midwest), MA seems to have a large variety of various conservation groups with property and easements; that large variety can sometimes make it hard to figure out what land can be walked on by whom.
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