The prettiest Northeastern towns to visit this winter for a cozy vacation

A two-hour train ride from Grand Central Station takes you to Poughkeepsie, a sleepy village about halfway between New York City and Albany. Home to the fabled Culinary Institute of America—the Harvard of culinary schools—Poughkeepsie holds a special place in the hearts of countless acclaimed chefs and restaurateurs. Gastronomic verve reverberates well beyond the CIA campus, and the Dutchess County burg punches well above its weight for spectacular dining.

For a white-tablecloth repast at a reasonable price, book a table at Escoffier, a traditional French brasserie run by aspiring young chefs at the CIA. In downtown Poughkeepsie, Brasserie 292 serves Francophilic comfort fare like duck confit and garlic-lashed escargot, prepared with the fresh bounty of the Hudson Valley’s waters and farms. For dessert, go with a plate of warm, pillowy beignets paired with a glass of cognac—a perfect tonic for a snowy night. Indulge in glasses of liquid warmth at the recently opened Dassai Blue Sake Brewery. Considered Japan’s sake house par excellence, Dassai brews koji-fermented ambrosia crafted with coveted yamada nishiki rice imported from Japan.

Spend an afternoon perusing the famous Hyde Park Farmer’s Market, an outdoor fair bustling with greengrocers, cheesemongers, butchers, craftsmakers and live music. The trails along the Hudson River and through Poughkeepsie’s hills are meditatively serene in the winter, and the city offers detailed digital maps of the best routes. For a more relaxed stroll, spend an afternoon marveling at regal gardens and a Gilded Age estate at Vanderbilt Mansion ($10 per ticket).

A four-hour car ride from New York City through Southern Vermont’s lush farm country brings you to picture-perfect Londonderry. Many come for the manicured slopes of nearby Stratton Mountain, but this Green Mountain jewel—awash with general stores, mom-and-pop ice cream parlors, and farm-to-table restaurants—enchants skiers and non-skiers alike.

As the nights wax longer, plan a deliciously romantic weekend at Seesaw’s Lodge, a historic Vermont lodge. Over its century lifespan, the timbered chalet has served as a clandestine brothel, a private club for ski-crazed bluebloods, and, nowadays, a sumptuous mountain retreat. Blending rustic charm with luxury, cabins at Seesaw's boast outdoor jacuzzis, full kitchens, and voluminous clawfooted bathtubs. Seesaw’s restaurant serves all the scrumptious goodness of Vermont’s countryside—boards of local charcuterie, poutine topped with Vermont cheddar, and, of course, sweet finales laced with maple syrup.

You could be forgiven for spending the entire weekend holed up in your cabin with a special someone, but when you’re ready to explore Londonderry, grab a maple cappuccino from Bromley Market, an epicurean general store next to Seesaw’s. HoneyPie, a vintage gas station turned into a burger-and-fries shack, serves the kind of satisfying, stick-to-your-ribs fare ideal before frosty afternoon adventures. For a fantastic dinner, book a reservation at SilverFork, a farm-to-table restaurant housed inside Londonderry’s former public library.

From Penn Station, a two-hour train ride along the misty banks of the Hudson River takes you to the heart of the Catskills and the town of Hudson. While a quiet riverine burg today, Hudson once rivaled New York City and Albany as the Empire State’s busiest hub of commerce. The railroad ultimately quashed New York’s inland shipping industry, but Hudson’s regal architecture and stately public squares still attest to its former Gilded Age opulence.

Drawn to upstate New York’s cornucopia of organic produce, meat, and artisanal cheeses, a bevy of elite New York City chefs have opened restaurants in Hudson in recent years. For a gastronomic tour-de-force of the Hudson Valley, book a table at Wm. Farmer & Sons, a luxuriously renovated 19th-century guest house. Co-owner and head chef Kirby Farmer crafts seasonal tasting menus celebrating the sparkling fresh ingredients of upstate New York’s rivers, farms, and forests. After dinner, indulge in a nightcap at the guesthouse’s gorgeous bar. Designed in partnership with legendary New York City mixologist Richie Bocatto of Dutch Kills, the craft cocktails are alone worth the trip from the city.

Three and a half hours by car from Boston, deep in the Adirondacks, Bolton Landing was America’s first major vacation destination, summoning throngs of carriage-drawn Victorian tourists eager to soak in medicinal hot springs around Lake George. One of America’s most historic hotels, the elegant Sagamore Resort, nestled on the shores of Lake George, was once a favored retreat of industrial titans like Rockefeller, Vanderbilt, and Morgan.

Helmed by a Tar Heel pitmaster imported from the hollers of Asheville, The Gem smokes the tastiest North Carolina-style barbecue this side of Goldsboro. Plates piled with applewood-kissed pulled pork or baby back ribs pair wonderfully with Little Gem’s selection of gourmet cocktails or draughts of Hudson Valley craft. Guests at the quirky Trekker Base Camp, set back in the woods outside Lake Geroge, can book nights in a hobbit hole or a retrofitted airplane. To stave off that post-sunset temperature drop, grab a bottle of red or a bottled cocktail at Little Gem, an upscale wine shop next to The Gem.

Funky Northampton, five hours by train from New York and one hour from Boston, has long been a haven for authors, poets, and eccentrics. Home to an array of elite liberal arts colleges, Northampton buzzes with music, the arts, and counter-cultural verve. To keep so many young scholars happily caffeinated, the stately streets of Northampton bustle with excellent third-wave coffee shops. The Haymarket Cafe is a favorite collegiate haunt, equally popular for expertly pulled espresso as for delectable vegetarian cuisine.

After a strong coffee, grab a jacket and meander through the leafy college campuses of Hampshire College or Smith. Even in the winter, the dignified walkways and quads brim with student life. Head to LimeRed Teahouse, as peaceful and quiet as a Zen garden, to savor an impressive collection of rare teas from Taiwan and China, brewed on a tea board in the traditional gong-fu cha style.

Although only 50 miles north of Manhattan, North Salem, an 18th-century colonial town, is one of Westchester County’s least densely populated enclaves. North Salem’s rolling hills, pockmarked with ponds and wooded glades, rank among the nation’s most coveted equestrian country. Lace up your hiking boots and embark on a snowy hike past horse farms and small ponds in the majestic Mountain Lake Park.

When Manhattan’s French super-chefs yearn for a taste of Provence without hopping a flight, chances are you’ll find them at Cenadou Bistrot in North Salem. With a cellar stocked with treasures from Bordeaux and Burgundy, Cenadou amalgamates the flavors of the French Riveria with Northeastern luxury ingredients like Maine Lobster and Hudson Valley pork. Late autumn and early winter ripen apples to ruddy perfection, and Harvest Moon Farm & Orchard serves sweet treats like fryer-fresh crullers and hard apple cider.

Western Massachusetts' Pioneer Valley, undulating with mountains and crisscrossed with country roads, is one of New England's prettiest corners for autumnal leaf-peeping, but the valley's beauty remains just as sublime after the leaves fall. With white-washed church steeples, tidy parks embellished with gazebos, and the crisp mountain air of the Berkshires, Deerfield, two hours by car from Boston, is the archetypical New England colonial village.

Carb-load on plates of rich pasta at Giani Fig’s Restaurant before an afternoon of hiking or cross-country skiing. Later, throw back a pint with the local cast of characters at The Tavern, a charmingly divey sports bar. The soup of the day is always Guinness, and keep in mind that you can safely cheer for only two teams around these parts: the Red Sox and whoever beats the Yankees.

The colonial village of Stockbridge, three hours by car from both Boston and New York, could have been recreated from a Norman Rockwell painting. In fact, Stockbridge is the final resting place of the whimsical painter of nostalgic Americana, as well as home to the Norman Rockwell Museum. Framed by the Berkshires and adorned with snug clapboard homes, Stockbridge is particularly beautiful when garbed with fresh snowfall and enlivened with firewood aromas.

Stave off the cold with a fortifying glass of French wine and bistro classics like ham and gruyere sandwiches at The Lost Lamb. If you have a set of wheels and are up for an old-school New England diner, drive to nearby North Adams to Jack’s Hot Dog Stand, the kind of homey luncheonette that would have made Mr. Rockwell smile.

Two hours by car from New York City and Boston, Litchfield marries indoor delights like wine tastings and posh shopping with outdoor fun like cross-country skiing and hiking. The birthplace of writer and abolitionist Harriet Beecher Stowe, Litchfield is one of the Nutmeg State's most picturesque small towns. Spend an afternoon strolling the historic streets and admiring the handsome Federalist architecture before grabbing a memorable dinner at Saltwater Grille or Market Place Tavern.

Wedged between New York City and New Haven—arguably America's two best pizza towns—Litchfield abounds in delicious cheesy pies as well as upscale Italian dining. Hometown Pizza serves parmesan- and pepperoni cup-laden slices of heaven, perfect for a quick lunch or late-night snack. The centrally located Litchfield Inn, a Colonial Revival gem, offers comfy rooms and friendly service.

The stark beauty of the White Mountains has long beckoned weekend warriors armed with snow boots, skis, and sleds. Although just an hour outside Boston, the subdued rhythms of Milford feel worlds removed from the rush and roar of any major city. Like many of the Granite State’s towns, Milford was once a thriving textile manufacturer, but today, the red-brick mills lining the Souhegan River have mostly been converted to waterfront restaurants and bars. As soon as the Thanksgiving plates are cleared, Milford’s squares, gazebos, and streets scintillate nightly in a colorful galaxy of Christmas lights and festive decor.

If you’re in town on a Saturday, spend a morning meandering through stalls at the Milford Farmer’s Market, indoors after December. Banish frigid thoughts with spicy, endorphin-stimulating plates like pork griot and creole chicken at Ansamn, a Haitian eatery transporting the sunny vibes of the Caribbean to rural New Hampshire. Union Coffee Company pours artistically rendered cappuccinos to perk you up in the morning or draughts of New Hampshire craft to take a load off in the evening. For a quintessentially New Hampshire guesthouse, book a room at the Ash Street Inn, 15 minutes from Milford in nearby Manchester.