The southwestern corner of Massachusetts abounds with elegant villages and fertile farmland, with views of gently rounded Mount Everett, the second-highest mountain in the Berkshires with an elevation of 2, 602 feet, in the distance.
The classic New England villages of West Stockbridge and Alford, along with the handsome commercial town of Great Barrington, add variety to the serenely rural area. And, if you like antiques, you’re in the right place—the villages of Sheffield and South Egremont boast the highest concentration of antiques shops (most of them in handsome wooden, stone, or brick houses about 200 years old) in the state. Though the Great Barrington Challenge travels along the valley ways between mountains, there’s still more than 3, 500 feet of climbing to conquer along this scenic half-century route.
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