Pittsfield, Massachusetts

Population: 44,472
House styles: Colonial Revivals from the early 20th century dominate the streets here
Expect to pay: Period houses sell from $125,000 to $250,000, depending on their size and condition

Mention the city of Pittsfield, the official "Hub of the Berkshires," to some Massachusetts residents, and you might hear them snark, "They don't call it the pits for nothing!" While it's true that housing prices in the western portion of the state have taken a big hit over the past few years, Pittsfield's abundant cultural resources and ample opportunities for outdoor recreation have been luring residents from larger cities.

The Berkshires' picturesque mountain scenery and hiking and biking trails draw outdoorsy types, while the prestigious music programs and live performances at the Tanglewood Music Center, the Boston Symphony Orchestra's legendary summer home in neighboring Lenox, hit all the right notes for music lovers and arts-minded folks. Low housing prices mean that creative types can afford to buy here; they can also take advantage of programs offered by the Pittsfield Cultural Development Office, which provides scholarships and grants benefiting the arts and humanities. Add these and a number of other developments to the equation—including the world-class Colonial Theater and the award-winning Barrington Stage Company—and Pittsfield's prospects are looking better every day.

Among the best for: The Northeast, Retirees, Family-Friendly, Lots to Do, Parks and Recreation
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