Cheshire Harbor Trail, Mount Greylock, Lanesborough, MA

See more in our guide to 55 Amazing New England Hikes.

At 6.6 miles roundtrip, this trail offers the easiest route up to the Bay State’s highest point—3,491-foot Mount Greylock—and can be completed in four to five hours.

Level: Moderate | Distance from Boston: 151 miles
Lanesborough, MA, 413-499-4262, website.

Photo courtesy of Ryan Taylor on Flickr

Photo courtesy Ryan Taylor on Flickr

hike iconInstagram-worthy views
hike iconTrails for two-wheelers