Located in Western Massachusetts and Connecticut, the Berkshires are home to a vibrant music and arts scene, along with some of the most dynamic fall foliage in the United States. While there are plenty of outdoor activities that allow visitors to get back to nature, the Norman Rockwell Museum in nearby Stockbridge, Mass. is a trip back in time. Admission can be combined with a visit to the MASS MoCA (the Massachusetts Museum of Contemporary Art) in North Adams, Mass. for a $5 savings. 

Mark Your Calendar: The two-day Lenox, Mass. Apple Squeeze Festival turns the town's Main Street into a celebration of the eponymous fruit on September 22 and 23. Fresh fall produce, baked goods, and tractor rides make this a classic autumn tradition (this year’s is the 33rd edition). 

Stay the Night: Massachusetts might be Red Sox country, but it’s the Yankee Inn in Lenox that stands out. Free breakfast, complimentary Wi-Fi, and seven different room types spread out over three buildings make this peaceful retreat a perfect home base while in the Berkshires. Rates from $109/night

— Mike Barish