America’s Prettiest Towns in the Winter

This winter mecca for outdoor enthusiasts is becoming less of a secret gem with every passing year. Visitors who come to this picturesque town in Idaho will find themselves within close proximity to several ski areas like Bald Mountain and Sun Valley, as well as other activities in Sawtooth National Forest and Galena Peak. There’s also loads of literary history to uncover (this was Ernest Hemingway’s final residence and he loved to fish and hunt here). Ketchum’s tidy downtown offers boutique hotels and resorts, upscale shops and galleries, fine-dining restaurants, and live music events that ramp up during the winter months. For night owls, the town has also been awarded the Gold Tier status from the International Dark-Sky Association (the first in the country), and nearly a million acres near town are part of the Central Idaho Dark Sky Reserve. Stargazers can pack a thermos and head to Sun Valley Lake for the best views.  

Just because it’s not beach season doesn’t mean there aren’t plenty of reasons to visit Nantucket, the island off Cape Cod. If you travel here in the winter, you’ll have far fewer crowds, off-season prices, and (unbeknownst to many) less frigid temperatures than the mainland. Keep an eye out for Nantucket’s annual holiday celebration that starts the day after Thanksgiving. During this time, hundreds of festooned Christmas trees line downtown Nantucket’s cobblestoned streets. Elegant local shops offer mulled wine, deserted beaches beg for romantic walks, and reservations are a cinch at the island’s best restaurants. To get here in the winter, there are several daily passenger and car ferries, or you can connect in Boston Logan International Airport for a 40-minute flight. With any luck, you’ll get caught in a snowy Nor’easter and have to stay a few extra days.

Surrounded by three freshwater lakes, Charlevoix in northern Michigan sees an influx of summer crowds during boating season. However, those who brave the winter will be rewarded with its pristine setting, which lends itself to frequent snowfalls (attributed to lake-effect snow). Charlevoix’s picturesque downtown is highlighted by its main strip, Bridge Street, where maturing trees are adorned with holiday lights. After browsing the local shops and galleries, bundle up and stroll to the marina, explore the Earl Young mushroom homes, and visit the lighthouse on the pier where winter waves from Lake Michigan can get fierce. Within a short drive are more great towns like Petoskey, Harbor Springs, and Boyne City (though none have the drawbridge like Charlevoix). Plus, the entire region is known for downhill and cross-country skiing, snowmobiling, and occasional Northern Lights sightings. 

Entering Vail, a Colorado town that was modeled after European alpine villages like Zermatt in Switzerland, is like stepping inside a fairytale. Located at the base of one of the country’s most popular ski mountains, Vail opened for its first season in 1962 after being built from the ground up (other Colorado ski areas were mining towns first). You’ll hardly have time to consider the lack of history here, with its wide, pedestrian-friendly (and heated) streets offering a plethora of stylish restaurants, après-ski bars, and ritzy lodging options that attract winter travelers from all over the world. Nearby slopes offer over 200 trails, 31 lifts, and other snow-focused activities. Meanwhile, non-skiers can take sleigh rides, go dogsledding, enjoy snowshoeing, or head to a mountainside hot tub or day spa. Yes, Vail sets a high standard when it comes to family travel in the winter. It also helps that there’s an idyllic ice-skating rink smack dab in the town center. 

Set within Vermont’s low mountains and dotted with church steeples, this quintessential New England town oozes with yesteryear charm and even more so when blanketed with a fresh coat of snow. Strolling through Woodstock’s village takes just a few minutes. Here, you’ll find the elegantly preserved Woodstock Inn, circa 1892, along with Federal and Greek-Revival houses and stately homes along the Ottauquechee River. Spend your days exploring the area’s antique stores, cheese farms, and covered bridges (there are three!), or hit the slopes. In fact, you can catch a free shuttle to Suicide Six, Woodstock’s ski area, and then finish the day by dining on fondue or thin-crust pizza. If you’re staying at the inn, return to find complimentary hot cocoa and tea in front of the massive lobby fireplace.

Northern California’s Monterey Bay is hardly a snow destination, but that's exactly why it’s on this list. Though temperatures dip in the winter season, Carmel-by-the-Sea offers a distinctly Mediterranean climate. Here, invigorating beach walks lead to spotting migrating humpback whales in the distance. The town itself is known for quaint bed-and-breakfasts, local shops, restaurants, galleries, museums, wineries, and charming houses that have no street numbers (mail is retrieved at the local post office). There are also no traffic lights, chain names, or fast-food joints. Walk along Scenic Drive to see these preserved homes along the beach. For nature lovers, there are plenty of activities that do not require a ski jacket. Drive to dozens of coastal trails, explore John Steinbeck history, and take day trips to Pebble Beach and Big Sur along the newly-reopened Highway 1. 

Halfway between Philadelphia and New York City, this preppy New Jersey town is best known for its ivy league university, but Princeton is much more than just a college town. The downtown area’s pretty streets and alleys (best with a dusting of snow) hold boutiques, bookstores, upscale restaurants, ice cream shops, and even an indie cinema. Come during the holidays when Princeton reveals a lovely set of decorations, especially in Palmer Square, and late-night store hours. After wandering through town, take a wintry walk around campus -- the set of many films -- and search for key buildings in the Gothic Revival style. Enjoy a free choral concert at the Princeton University Chapel or visit the Frist Campus Center (former physics laboratory) to see where Albert Einstein lectured. He spent the last 22 years of his life here and it’s easy to imagine him taking nature walks, playing violin, and discussing quantum theories with his colleagues. You’ll never be more inspired to set up shop in the library -- this is intellectual inspiration at its finest.  

Located on Baranof and Chichagof Islands, the breathtaking town of Sitka is known for its natural scenery of snow-capped mountain peaks and sea. Plus, the fact that it is only accessible by air and sea helps keep the crowds at bay. Those who do come here -- often cruisers since this is a popular port of call -- get the chance to explore the downtown area where most points of interest are within walking distance of one another along the waterfront. There are 22 places on the National Register of Historic Places where you can learn about the town’s Russian heritage and trading settlement. In addition checking out the museums, historic sites, and onion-domed cathedral, visitors can talk to friendly locals to learn more about the town. For outdoor pursuits, head across Sitka Sound to the impressive Mount Edgecumbe, a dormant volcano with a cone similar to Japan’s Mt. Fuji. Hiking and wildlife-viewing are among the many outdoor activities available. 

This postcard-perfect New England town may be best known for its glittering summer coastline, but from Thanksgiving to mid-March (after the crowds retreat), it transforms into a peaceful winter wonderland. Kennebunkport’s downtown area, along Dock Square, is peppered with colorful buildings housing specialty shops and cozy restaurants that peek through the regular fresh dusting of snow. For short excursions, drive past the beautiful homes along Ocean Avenue, take a deserted beach walk, and visit nearby farms like Laudholm and Harris. Active types can go Nordic skiing and snowshoeing in the fields and winter woods before heading back inside for a hot chocolate by the fire. During the holidays, Kennebunkport puts on the Christmas prelude -- a two-week event starting in early December with Christmas carols at the Franciscan Monastery, horse-drawn sleigh rides, and Santa arriving by lobster boat. Meanwhile, in February, couples will find Valentine’s Day hotel specials, wine and cheese tastings, and romantic candlelight dinners.

Best known for its Oktoberfest and Christmas-lighting ceremonies, this scenic Bavarian-style village in Washington’s Cascade Mountains is magical in the wintertime, and a favorite weekend getaway for Seattleites. The historic downtown, once a former mining center, is now home to gingerbread architecture, kitschy stores, quaint lodging options, and restaurants that prepare Bavarian-influenced dishes. Even the local gas stations and supermarkets stick to the German theme. The area also offers lots of outdoor sports. With plenty of trails and nearby Stevens Pass Mountain Resort, there are endless opportunities to go hiking, resort skiing, and backcountry alpine skiing. Return to town and load up on brats, beers, and schnitzels, or stop by one of the many international restaurants and cozy wine bars.

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