Through Lee, Becket, Chester, Huntington, and Russell
If you want to ogle the best of the best of the Berkshires, then you need to take a spin on Jacob’s Ladder Trail. Also known as Jacob’s Ladder Scenic Byway (and Route 20), this meandering drive was built in 1910 because cars were suddenly a big deal and folks wanted a way to cross the mountains in their new rides. And what a way to kick off the age of the automobile. The route is bedazzled with numerous scenic overlooks, trail heads, parks/forests, and charming towns, so you can choose your own adventure. Must-sees include the summit marker (at 1,775ft) near Becket, the waterfalls in Chester-Blandford State Forest, October Mountain State Forest (Lee), and the Keystone Arches, the stone bridge relics from when trains were a big deal.