Runner-Up: Manchester, New Hampshire

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Prisma Bildagentur/Alamy Fall foliage in Manchester

Key Stats:

  • Population: 110,400
  • Over 50: 33%
  • Ski resorts within 100 miles: 64

Pros: New Hampshire’s largest town has big-city perks, including a 11,770-seat sports and concert arena, a large regional airport, and the Currier Museum of Art, which houses works by Picasso and Monet.

Still, Manchester retains many of the best qualities of a smaller place, with low crime and little urban sprawl. It’s also close to many other great New England destinations: Boston is just 50 miles away, and the White Mountain National Forest is less than two hours to the north.

Cons: The housing market here has been slow to recover, with many homes still under water.

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