Jacob's Ladder Trail - Drive to a simpler time, a time of innocence and beauty. Discover for yourself the scenic charm that made “the First of the Great Mountain Crossovers” the first great attraction of the motor-touring era. Come and explore the enchanting historic byway of yesteryear, Jacob’s Trail Ladder.

Jacob's Pillow Dance Festival - Oldest dance festival in America. The Pillow was designed by Joseph Franz, the renowned architect who was responsible for the Tanglewood Shed. Jacob's Pillow was founded in 1942 by Ted Shawn.

Jiminy Peak - You'll find an awesome range of over 33 trails - including New England's steepest night terrain, a vertical drop of 1,140 feet, 8 lifts, moguls, bumps, and long cruisers. From expert to beginner, from NASTAR to SKIwee. You'll find it all at Jiminy Peak.

Josh Billings - The scenic course starts at the Price Chopper Plaza (on Rte 7) in Great Barrington, MA with the 27-mile bike leg. This first leg finishes at the Stockbridge Bowl Boat ramp off Rte. 183 in Stockbridge, where the hand-off to the canoeist takes place.

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