While this is more the ghost of an old ski area than an actual working resort, Mt. Greylock is home to one of the most important runs in East Coast ski history: The Thunderbolt Trail, a 1.5-mile, 1,700-foot vertical, ski racing line from the summit that was hand-carved way back in the 1930s. At 3,491 feet, Mt. Greylock is Massachusetts' highest natural point, so it's no surprise that adventurous East Coast skiers of yore decided to build a ski run on it. And it actually became the site of some very important pre- and postwar races. While no lifts were ever put up, skiers, and those just hoping to catch a glimpse of the action, would catch a ride to the top in local farmers' sleighs. It fell into disrepair in the '70s, becoming almost unskiable, but has been revived in recent years by a devoted crew of volunteer stewards. Today, skiers from all over the East hike or skin to the top for access to its legendary sweeping turns like Big Bend and tight squeezes like the Needle's Eye.
Where to stay: The Porches Inn in North Adams is a classic Berkshires getaway, just 15 minutes from the trailhead at Mt. Greylock.
Insider Tip: Check out thunderboltskirun.com for all the history and access info you could want, including an update on the vaguely annual race commemorating the first competition in 1935, where skiers try to beat the course record of 2 minutes and 8 seconds set in 1948.