Steepest Ski Trail in Massachusetts, Upper Liftline, Jiminy Peak

The trails of Jiminy Peak are carved into Potter Mountain which is situated along a major  ridgeline within the Taconic Mountains of Western Massachusetts. The ridgeline has a couple major peaks, one being Jiminy Peak and the other being Widow White’s Peak (named after a previous landowner).  The ski area was due to open in the winter of ’47-’48, but due to excessive snow the construction couldn’t be completed. The area officially opened for the 1948-49 ski season with a pair of rope tows and a T-bar.  The area then underwent two major expansions first in 1964 and then in 1998. From the opening of the resort until 1964, the pinnacle of Jiminy Peak was the Merry Go Round trail. However, in 1964 a double chairlift was installed add more vertical to the mountain along with some new trails. Jiminy Peak expanded onto Widow White’s Peak in 1998 opening up five trails, mostly intermediate.

Upper Liftline

Pop Quiz…What do Upper Liftline (Jiminy Peak), DJ’s Tramline (Cannon) and Devil’s Fiddle (Killington) have in common?  If you guessed they are three of the hardest trails in the east, you would be wrong!  However, if you guessed all three trails are rarely open, due to lack of any fans or nozzles which blend compressed air and water to create dust on crust – you are correct. This is a somewhat interesting fact because 96% of Jiminy Peak has snowmaking.   However, when the Liftline trail is open, which does occur after a couple heavy snow falls or a consistently productive winter, you will find a 44 foot wide trail that offers up a sustained pitch of 28.23 degrees making Upper Liftline the steepest trail in Massachusetts. When the rope is dropped on the trail, you will be rewarded with a trail that can become a mogul field. As you have probably guessed, based on the name of the trail you will have attentive audience above you on the Berkshire Express while you navigate this steep, narrow bump run.  The downside is the trail is short and dumps out into a maze of green circle trails.

There is an interesting story circulating about this trail that involves the Kennedy’s.  In the 1970’s, Ted Kennedy and his family would frequent the Berkshires and spent time skiing at Brodie and Jiminy Peak.  At the time, Brian Fairbank was the CEO of Jiminy and invited Ted Kennedy to ski Upper Liftline with him, to which he accepted.  When Kennedy reached the bottom of the trail he turned to Mr. Fairbank as stated, “What are you trying to do, kill me?". The quote is a little spooky since Senator Kennedy’s nephew, Michael, was killed in a skiing accident in 1997 at Aspen.