There comes a time each summer and fall when hiking has become so chic as a seasonal activity that a lot of us write off the prospect of visiting superlative destinations like Mount Monadnock or Greylock. I’ll wait until November, when those goddamn leaf peepers have gone back to the West Village, you mutter as you brood on the porch with a smoldering blunt or a half-drained can of beer. We’ve all been there.
But if I’ve learned one thing over 20+ years of snooping around New England’s woods and meadows, it’s this. Like any castle or citadel, most major trails have at least one lesser-known back entrance. And thanks to the advances of digital mapping tools like Google Maps and AllTrails, it’s never been easier to find and enter these “back doors.”