I haven't spent much time in Massachusetts, but my impression is that the woods there are a lot thicker than they are out west. Even here, there have been times I have had to find some place out from under the trees to get a gps signal. Plus, like any toy, a gps can break, so you should still have some alternative means of finding your way back. But they are a great help, and I use one all the time, in or out of the woods.
One of the things you might consider is one of the new gps watches. Mostly they don't have maps built in, but the one I looked at that did have a map, the map was so small I decided it wouldn't be of much use anyway. But what they do have are simple ways to find your way back to the place where you started. One click when you leave the truck and it starts recording where you are. Two clicks when you want to go back and it takes you back where you started.
One advantage of a watch is that if you like it enough, maybe you'll start wearing it all the time. Then whenever you have an odd moment or two, you'll start fiddling with it to figure out all the things it does. The first one I got, several years ago, didn't have much battery life, and so wasn't really that useful for extended trips in the field. But the one I have now keeps a charge for a long time. I recently returned from a two week trip to Peru, where I always used the watch for the normal functions, such as time, compass, and elevation, and occasionally used the gps when I didn't want to get lost wandering around in a strange town. It was still more than 50% charged at the end of the two weeks.
I have a map on the larger Garmin gps I have, but to be honest with you, I don't really need it. I know enough about the area I'm in to know generally where lakes, rivers, and mountains are, and do carry a regular paper map. I use the gps for when the terrain is confusing and there isn't a big old mountain sticking up somewhere that I can use to orient myself. I also use it to mark my kill, so I can find my way back to it. Marking your kill as a waypoint requires a few more clicks than the basic feature to find your way back to your truck, but it's well worth learning how to do it. Heck, I learned how to do it, and I'm 71.