I do almost all of my snowshoeing by bushwhacking right out of my house, so one of the big advantages is not having to worry about some of what the other posts are talking about. All this talk about ski tracks and overused trails, I can understand it on a theoretical level but it mostly doesn't apply if you just head into a space where you're the only one tracking it.

To be clear, I'm not contradicting the other advice given in this thread. Lots of solid input.

For me, it just reduces down to dress appropriately, have the right length shoes for your size, bring stuff you'd usually bring for hiking, let someone know roughly where you will be, and go. You don't need a defined trail, and with Vermont's land regulations there are tens of thousands of acres available to you across the state. Another advantage to breaking your own track is that it'll be super easy to follow if some kind of problem arises, as unlikely as it might be, as long as someone knows basically where to start.

As a whole though snowshoeing is pretty much the easiest of winter sports to prepare for. A bit more strenuous per meter than hiking, but easy to learn and with a great deal of route flexibility. Have fun in the woods!