The Best Winter Weekend Getaways from Boston

Although Kennebunkport is a summer staple for its lobster shacks, quaint lighthouses, and windswept beaches, come winter, this coastal town is the perfect quiet escape for seclusion-seekers. In January and February, Kennebunkport celebrates Paint the Town Red, when Dock Square is covered in red twinkly lights and an eight-foot-tall heart made of lobster traps is erected in the town center. Hotels, stores, and restaurants also host a month of romantic events, wine tastings, and more. Don’t miss the Bubbles & Truffles chocolate-making class at Ocean, an upscale Mediterranean eatery at the waterfront Cape Arundel Inn and Resort, or dinner à deux at The Burleigh, where you can feast on Maine mussels and braised short ribs.

This Green Mountain State enclave, known for its hippie-meets-hipster vibe, is a great winter getaway. Bed down at the Hotel Vermont, which has rooms done up with throw blankets by local artisans, reclaimed wood furniture, and, in some, gas fireplaces. Start the day off with a decadent brunch at Butch + Babes, a Old North End newcomer that serves mac and cheese pancakes as well as a veggie bowl with cheddar grits and poached eggs. Afternoons can be spent exploring the contemporary art galleries and studios at Burlington City Arts and browsing the boutiques along Church Street. (JS Tip: Stop at Burlington Records for some vintage vinyl finds.) Thirsty? Foam Brewery pours farmhouse ales and IPAs—our favorite is Let the Funk Flow, a golden sour beer fermented in 200 pounds of pineapple. For dinner, Juniper Bar & Restaurant cooks crowd-pleasing dishes such as Grilled Starbird wild salmon with cranberry glaze and cassis beurre blanc; mole-braised spaghetti squash; and Northeast cioppino with sautéed hook and line pollack and mussels.

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Rhode Island’s cool-kid capital mixes a creative culinary scene with historic charm. Drop your bags at The Dean—the 1912 church house has been transformed into a stylish 52-room hotel with vintage European artwork, a sultry cocktail bar, and a karaoke lounge—then take a tour of Brown University’s meticulous campus to learn about the city’s collegiate roots. A few blocks is the Rhode Island School of Design (RISD) Museum, which is home to 100,000 objects from ancient art to designer textiles. History buffs will want to check out the area’s historic houses—see Stephen Hopkins, John Brown, and Henry Lippitt—which date back to the 18th century. When hunger strikes, Oberlin is the place to go. Celebrated chef Benjamin Sukle is at the helm of this wine bar and raw bar combo, which serves yellowtail flounder, Nantucket Bay scallops, and gnocchi with shellfish.

This whimsical Vermont hamlet may be small but it has a mighty art and culinary scene. Fuel up for the day at Mon Vert, a cute coffee shop and café that makes a mean maple latte and panini—opt for the Devil on Horseback topped with bacon, Vermont Creamery goat cheese, and walnut date spread. On a sunny afternoon, stroll by the covered bridges in the Marsh-Billings-Rockefeller National Historical Park, the state’s only national park, or head to the Billings Farm and Museum for a festive sleigh ride around the snowy landscape. Culture vultures will want to pop into the Simon Pearce glassblowing studio, just up the road in Quechee. After dinner at The Prince and The Pauper, a hidden gem that dishes up mouthwatering meals like cedar-planked arctic char or pork schnitzel, retreat back to the Woodstock Inn & Resort, a sprawling property with an award-winning spa, access to the Suicide Six slopes, and a nordic adventure center with 25 miles of on-site nature trails.

The bucolic Berkshire Mountains have long attracted Boston’s city-slickers. This picturesque region in Western Massachusetts is known for its famous resident Norman Rockwell, who lived in Stockbridge for 25 years and is now commemorated with his own museum of roughly 1,000 original paintings and drawings—the artist’s largest collection in the world. You can also tour Arrowhead farm, Herman Melville’s former home, or Wheatleigh, a 19th-century Italianate mansion set on 22 acres of manicured gardens designed by Frederick Law Olmsted. For your own royal digs, check into Canyon Ranch in Lenox, a wellness retreat featuring healthy gourmet restaurants, personalized fitness experiences, and a 100,000-square-foot spa. On cold nights, head to the cozy Lion’s Den pub to listen to live bands and sip mulled cider by the fire.

RELATED: Your Perfect Guide to the Berkshires: Where to Stay and What to See

Just 90 minutes northwest of Montreal, Mont-Tremblant makes an easy long weekend trip from Beantown. This Canadian ski resort is like a quick trip to Europe, complete with a pedestrians-only village covered in twinkling lights at the base of the slopes. Stroll along the snow-covered streets and try a maple syrup popsicle, which locals make by pouring syrup on frozen ice-topped oak casks. After a day of schussing down the 100 nearby trails, kick your feet up at the Fairmont Tremblant, a gorgeous mountain chalet with one of the region’s best restaurants, Choux Gras Brasserie. Here, you can tuck into French favorites such as roasted bone marrow, bouillabaisse, and duck confit. As for late-night activities, ride the gondola to the cliff-top casino to try your hand at cards or dance the night away during one of Bar Café d'Epoque’s legendary ragers.

Andover may not look like much at first glance, but this New Hampshire nabe has a strong arts program and family-friendly ski areas. A sweet German couple welcomes guests to the Highland Lake Inn, a charming B&B in a renovated 1767 farmhouse, and is happy to recommend local activities such as seeing a show at the New London Barn Playhouse or catching a film, concert, and comedy show at the Capitol Center for the Arts. Meanwhile, adventure-seekers can go dog-sledding with Valley Snow Dogz, skiing at Ragged Mountain Resort, or snowmobiling with the Andover Snowmobile Club.