My husband and I met sorting silverware at our work study jobs in the Williams College freshman cafeteria 41 years ago, so this is a completely biased review. Our last visit (our first in 12 twelve years) was at the end of the fall foliage season, but the area is truly beautiful in any season. We enjoyed walking around and seeing the changes on campus and in the town, but there are things to do and see that would make Williamstown a good stop for anyone touring the Berkshires. However, if you intend to stay overnight, it is worth checking the college event calendar on the Williams College website so you can avoid times when everything will be crowded. We did not check and our visit coincided with Family Weekend which meant that hotel/B&B rooms were in short supply.
Even if you don't have an emotional attachment to the college, it is the quintessential New England small liberal arts college campus and exudes that vibe. One should visit the Clark Art Institute and the Williams College Museum of Art which has expanded its collection and exhibit space since we took Art History 101-102. It is also a great area for walking and hiking. The hike up Pine Cobble is doable if you are moderately fit and you can drive to the trail head.
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