16. Litchfield, CT
Why go: Litchfield—which was settled in 1721—sits in the foothills of the Berkshire Mountains, making it an easy drive from Boston, New York, Albany, and Hartford. Peak foliage is on display in mid-October, and the best way to view it is by driving along from one charming New England town to the next. Get road trip inspo from The Litchfield Hills Visitors Bureau.
Where to stay: A classic country inn, the Mayflower Inn & Spa sprawls over 58 acres of Litchfield County. The hotel encourages guests to explore the area: Hike through the meadows and wetlands, bike along the banks of Lake Waramaug, make cheese at a family-run farm, tour a local bourbon distillery, or pick apples at a nearby orchard.
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