My take
I suspect you're right that someone saw this as an easy access point. Considering, however, that all of Rattlesnake is private property, why would anyone think it's ok to ride over someone's property (yard really in this case). They wouldn't go across someone's residential property on the mainland (or perhaps I give too much credit there too) because the owner might well be home and have something to say/do about it. It's simply that it's quiet around the islands in the winter and the less considerate folks out there think it's ok to go anywhere their sled will take them.
My advice would be to put up a snow fence and signs as part of your fall preparations. With luck, that's all the discouragement they'll need.
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