Massachusetts' Mountain With An Oddly Sad Name Has Stunning, Enjoyable Trails With Hudson River Valley Views

This Massachusetts mountain's oddly sad name sounds like something out of a fantasy novel, but in reality, it's a scenic landmark with stunning, enjoyable trails and Hudson River Valley views. Misery Mountain is a mountain ridge in the Taconic Mountains in the Berkshires. It spans about six miles in western Massachusetts and eastern New York, running from Williamstown, Massachusetts (a charming town with a vibrant arts scene) to Stephentown, New York.

There isn't a definitive answer to how Misery Mountain got its name. Some sources suggest it may be because of border skirmishes in the 1750s between Massachusetts and New York colonists, while others say it's simply because the tall peaks make the mountains a challenge to cross. But whatever you think of the name, Misery Mountain hikers are anything but miserable. There are many hiking routes through the mountains, including the Taconic Crest Trail, Robinson Hollow Trail, and Mills Hollow Trail. Outdoor enthusiasts praise its forest scenery, well-marked trails, local wildlife, and challenging hike. Depending on which trail you take and the time of year, views show fern-covered forests, Hudson Valley meadows, and Taconic peaks. "Highly recommend this trail for someone looking for solitude and a great workout!" writes one Alltrails reviewer.

Misery Mountain is partially privately owned and partially public, with many trails and forest roads leading to the mountain. You can begin your hike in Pittsfield State Forest in Pittsfield, Massachusetts or Hopkins Memorial State Forest in Williamstown, Massachusetts; at a parking area in Hancock, Massachusetts; Williamstown, Massachusetts; New Lebanon, New York; or North Stephentown, New York; or at a smaller trail beginning on either the Massachusetts or New York side of the mountains.

Wherever you enter from, you will need a car to reach the start of your hike. While there are many small towns in the area, nearby cities include Albany, New York, about 35 miles away, and Springfield, Massachusetts, about 75 miles away. The nearest major airport is Albany International Airport, about 40 miles away. There are plenty of hotel options close to Misery Mountain, including the charming Williams Inn in Williamstown, Massachusetts and the historic Hotel on North in Pittsfield, Massachusetts — a buzzing artsy city with world-class food and fun. Spending more time in the Berkshires? Don't miss Lee, "the gateway to the Berkshires," a postcard town with classic New England charms and cozy inns.