Kennebunkport, Maine

You can consider the more than 20 miles of trails at Harris Farm, a working dairy farm that welcomes outdoor enthusiasts each winter for breathtaking cross-country skiing near Kennebunkport. When strong winter swells driven by nor'easters entice devoted surfers in wetsuits, don't disregard a walk on the beach or even a surf in the chilly waters. Most people assume that this seaside resort is only open during the summer, but Kennebunkport's unique appeal really comes into its own when the weather turns gloomy and the rugged beauty of coastal Maine is brought into sharp relief.

It takes around five hours to get there from NYC, largely via I-95, but you can and should take a break in Portsmouth, New Hampshire, where Sanders Fish Market serves the greatest crab sandwich in all of New England. Don't overlook the on-site art gallery, which features a changing collection of works by regional artists. The White Barn Inn & Spa is the perfect destination for anyone seeking both privacy and pampering. The larger apartments include deep soaking tubs and—the ultimate in winter indulgence-gas fireplaces, while the historic inn and private cottages feature niceties like fresh flowers and Prima Fleur cosmetics. This is definitely one of the best winter getaways from NYC.

Location: Kennebunkport, southern Maine