A still-thriving fishing village combined with the tony aura of a wealthy resort town, Chatham, Massachusetts, has the look and feel of the quintessential seaside New England village. Sea-bitten cottages with winding roses look out to dramatic ocean views alongside stately, old-time family estates. The town's main street is ideal for strollers and shoppers, its sidewalks lined with dozens of interesting storefronts and restaurants. Each Friday night in summer, the village green comes alive with band concerts; the ample lawn is filled with families, balloons and dancing children. It is there that the mighty Atlantic Ocean first touches Cape Cod, its chilly waves melding with the calmer waters of Nantucket Sound.

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