39. Lexington, MA
Why go: Historic Lexington is known as the spot where the “shot heard round the world” rang out, but the bucolic countryside—just 20 minutes outside of Boston—is also ground zero for New England leaf peeping. For a combo of both, walk the Battle Road Trail, a 5-mile walking path that connects landmarks like the spot where Paul Revere was taken prisoner, or the 11-mile Minuteman trail.
Where to stay: Stay at The Inn at Hastings Park and you can schedule a 30-minute private helicopter tour to not only see New England’s fall colors from above, but also experience what it’s like to fly over the Boston Common, Fenway Park, and Harvard.
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