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The Sweetest Small Towns in the U.S. to Visit This Winter

By Ashlea Halpern

12.03.19

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Leavenworth, Washington, offers a Bavarian-style winter wonderland nestled deep in the Cascade Mountains.

Photo by Checubus / Shutterstock

Leavenworth, Washington, offers a Bavarian-style winter wonderland nestled deep in the Cascade Mountains.

Bigger isn’t always better when it’s time to get away. Case in point: These smaller, off-the-radar enclaves across the United States are well worth the wander come wintertime.

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Although it may be tempting to hole up and hide out during the coldest, bleakest months of the year, there’s a lot to love about winter if you’re willing to embrace the chill. We’ve rounded up more than half a dozen super-sweet small U.S. towns that have made an art out of winter merrymaking. So bundle up, strap on some snowshoes, and fill your flask with hot buttered rum—these charming winter getaways will cure even the nastiest cases of seasonal affective disorder.

Leavenworth, Washington

Deep in the Cascade Mountains, about 2.5 hours east of Seattle, awaits a Bavarian-style wonderland with strolling carolers, twinkling Christmas lights, and the scent of roasted chestnuts wafting through the air. Leavenworth’s German-influenced, timber-framed buildings are set against a backdrop of snow-blanketed mountains, making this Old-World fairy-tale village the stuff of postcard dreams. During its annual Christmas Lighting Festival, more than half a million bulbs glow with special tree-lighting ceremonies that take place during the first three weekends of December.

But the fun doesn’t stop there. Leavenworth also has a Nutcracker Museum with more than 6,000 crackers to its name (including ones dating back to ancient Rome) and the family-run Leavenworth Reindeer Farm, where travelers can feed, pet, and take selfies with woodland caribou. Other family-friendly outings include the Leavenworth Ski Hill, which has a 100-foot tubing hill and rope tow; the five-mile Icicle River Trail, popular with Nordic skiers thanks to its picturesque mountain views and breezy terrain; and old-fashioned sleigh rides at Red-Tail Canyon Farm. Over at Lake Wenatchee State Park, you’ll find 28 miles of well-groomed cross-country ski trails, including a leg starting just a stone’s throw from downtown.

Leavenworth is also a fine place to knock out a bit of holiday shopping: Hunt for wooden puzzles at the Wood Shop, loose-leaf teas and herbal tisanes at Cup and Kettle, German cuckoo clocks and steins from Alpen Haus Gifts, and boxes of elegant chocolates from Schocolat. When your feet need a rest, slip into Doghaus Brewery, a nanobrewery housed in the former morgue of the Cascade Sanitarium.

There is no shortage of places to stay in Leavenworth, including several behemoth hotels. For a more intimate experience, head to Abendblume B&B, a romantic storybook inn with seven beautifully appointed rooms. Ask for the Tannenbaum unit, a handsome suite with two fireplaces, a whirlpool tub, wet bar, and a balcony from which to take in panoramic views of the Cascades.

Cross-country skiers flock to Copper Falls State Park near Ashland, Wisconsin, to whoosh by dramatic gorges and frozen waterfalls during winter.

Ashland, Wisconsin

This Photoshop-pretty port town on the southern side of Lake Superior is home to only 8,209 people, but it boasts an Olympic Village’s worth of outdoor activities. Snowmobilers can choose from more than 200 well-maintained trails, while cross-country skiers flock to Copper Falls State Park in Mellen, 25 miles north, for a quartet of loops cutting past dramatic gorges and frozen waterfalls. Downhill skiers, meanwhile, get their kicks at Mt. Ashwabay in Bayfield, 21 miles south, where the longest run is 1,500 feet and the highest vertical drop 317 feet. Time your visit to February 15, 2020, to partake in Ashland’s 24th annual Book Across the Bay, an event that sees thousands of competitive and recreational skiers and snowshoers trekking six miles across frozen Lake Superior—at night, with the course lit solely by candles and stars. (BYO gear or plan to rent skis or snowshoes at Solstice Outdoors.)

The town of Ashland sits right on Chequamegon Bay, an inlet of Lake Superior, and is best known for its smallmouth bass fishing in summer. But the subzero temperatures don’t stop bundled-up anglers from hunting for lake trout, coho salmon, whitefish, walleye, and perch in winter. To try your luck at ice fishing, book a half-day or full-day outing with the pros from Jeff Evans Fishing, a Wisconsin outfitter founded by a U.S. Coast Guard charter boat captain.

It’s easy to get distracted here by the great outdoors (tip: Ashland also makes an excellent base for exploring the magnificent ice caves on Apostle Islands National Lakeshore, about 40 miles away), but the downtown area is ridiculously charming, too. Take a self-guided tour of the eight-block Main Street business district to see why Ashland is nicknamed the “Historical Mural Capital of Wisconsin”; tuck into wild rice meatloaf or a Cajun-style Lake Superior whitefish sandwich from Deep Water Grille; or warm your bones with an Old Fashioned from H.P.L. Bar, the closest this low-key town gets to Chicago-caliber craft cocktailing.

Whatever you get up to by day, build your nest at night in one of six rustic suites at the Northwoods forest-inspired Second Wind Country Inn, where the rooms have evocative names like Pine Cone Hollow and Lumberjack Loft.

The small town of Dahlonega, Georgia, turns up the wintertime cheer during its six-week Old Fashioned Christmas celebration.

Dahlonega, Georgia

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Think the cheerful streets of this north Georgia town look like they belong in a Hallmark movie? You should be a location scout. The 2016 hit rom-com Christmas in Homestead was filmed here, and like that film’s made-up, Christmas-crazy village of Homestead, Iowa, this 7,007-resident town is wild about all things Saint Nick.

Kicking off its six-week Old Fashioned Christmas celebration on November 29, Santa Claus sets up shop at the Visitors Center Plaza Downtown; carolers sing to passers-by cupping hot cocoa; and extravagant light displays glitter in storefront windows. There are Christmas parades and mistletoe bazaars, a dramatic tree-lighting ceremony in the town square, horse-drawn carriage rides, ugly sweater wine tours, holiday concerts by the North Georgia Chamber Symphony, and sleigh bell tours of the Inns of Dahlonega, a league of dressed-to-the-nines bed-and-breakfasts.

The five-bedroom Old Storehouse Inn, in particular, is a delightful B&B on North Meaders Street, walkable to most of the festivities. After you’ve had your fill of Christmas cheer, devote a day to seeing everything else that makes Dahlonega a popular Southern getaway. Make the rounds to the tasting rooms of local wineries and vineyards (Cavender Creek, Wolf Mountain); pan for your retirement at the 122-year-old Consolidated Gold Mine; or spend an afternoon outdoors scouting the area’s many waterfalls, including a stunning 600-foot cascade in Amicalola State Park.

Ogunquit, Maine

Winter may seem like an odd time to visit New England, but one glimpse of this coastal community in southern Maine and you’ll swear you stepped inside a snow globe: Ogunquit’s 921 residents take their holidays seriously. Annual Christmas by the Sea festivities include gallery tours, choral concerts, a tree-lighting ceremony at Veterans Park, visits with Santa Claus, an annual arts-and-crafts showcase at the local fire station, ornament-making workshops, hay rides, and a beachfront bonfire that ends with a respectable blast of fireworks. The high point, however, might be the Ogunquit Ocean Rescue Polar Plunge, where local service members take a quick dip in the frigid waters of Ogunquit Beach as part of a Toys for Tots fund-raiser.

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Missed the memo? No problem. Anytime is a good time to wander the docks at scenic Perkins Cove, with brightly painted rowboats and fishing dories bobbing against snow-caked cliffs. Put on ice cleats and crunch along the 1.7-mile Marginal Way, a public walking path that hugs the shoreline and showcases some of the town’s grandest houses. For a more adventurous outing, hit the snowshoeing trails in the nearby Mount Agamenticus Conservation Region, the largest swath of coastal forest between Acadia National Park and the New Jersey Pine Barrens, or go downhill skiing at Powderhouse Hill in South Berwick, 30 minutes west of Ogunquit.

To sleep, reserve one of eight rooms at the 119-year-old Rockmere Lodge, a traditional shingled Victorian overlooking the Atlantic ocean. While it’ll be too chilly to hang out on the wraparound verandah, guests are welcome to huddle around the B&B’s Italian-tile fireplace, mug in hand, and admire the inn’s myriad Christmas displays.

El Santuario de Chimayó, located north of Santa Fe, New Mexico, is said to contain “holy dirt” capable of miraculous cures.

Chimayó, New Mexico

To travelers who won’t embrace a snow drift no matter how many tree-lighting ceremonies we throw their way, we offer Chimayó, a sweet dream of a winter getaway in the American Southwest. Just 40 miles north of the snowbird paradise Santa Fe, this mystical little town has 3,177 residents, a robust textiles scene, and dirt so sacred that people come here from all over the world to touch it.

Although Pueblo Indians lived in this neck of the Northern Rio Grande Valley for thousands of years, the village of Chimayó wasn’t officially “founded” until 17th-century Spanish settlers swept in and claimed it. The first stop for first-timers is usually the beautiful El Santuario de Chimayó, a national landmark whose Our Lord of Esquipulas Chapel was completed in 1816; its Holy Child of Atocha Chapel followed four decades later. Worshippers make pilgrimages on bare feet to get here, specifically to visit “el pocito,” a tiny room to the side of the altar where there is a dirt hole in the stone floor. Disciples get on their knees to scoop hallowed earth from the hole and rub it on their hands and feet, crucifixion-style. Some people bottle it up and bring it home, believing it can cure arthritis, depression, and even cancer.

The Chimayo Museum, located in the hamlet’s once heavily fortified Plaza del Cerro, is another must-see (though it’s only open on Fridays in winter). It’s housed in a traditional adobe home with white-washed, mud-plastered walls and hardened mud floors. Swing by to browse photographs from early 20th-century Chimayó, many of which were taken by missionary school teacher Prudence Clark.

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Despite its small population, Chimayó has an enviable clutch of excellent handicraft shops. Handwoven vests, coats, blankets, rugs, pillows, place mats, and purses are all for sale at Ortega’s Weaving, a family-run store whose heritage crafting traditions date to the early 1700s. At Centinela Traditional Arts, Lisa and Irvin Trujillo work with a group of longtime spinners, weavers, and colcha embroiderers to produce natural-dyed, handwoven wool blankets and rugs, many in the signature Chimayó style (two stripes and a center design, an outgrowth of Saltillo tapestry techniques). The nearly century-old El Potrero Trading Post, meanwhile, sells Mexican tin retablos, bultos, Zuni fetishes, and petite bags of molido, a potent powder made from sun-dried Chimayo heirloom chilies.

When it comes to a home base, you can’t beat Casa Escondida, an antiques-stuffed B&B with nine rooms (five of them pet friendly). From the gorgeous kiva fireplaces and Saltillo tile floors to the ristras of dried chilies hanging on the front porch, this place checks all the right boxes.

Lewisburg, West Virginia

Fewer than 4,000 people get to call this beguiling mountain town in the heart of Greenbrier Valley home, but that’s good news if you’re swooping into the area for a break from a buzzy city. Drop your luggage at Maison Marcel, a 1920s manor house turned B&B less than one mile from downtown Lewisburg, and head for the nearest leg of the 78-mile Greenbrier River Trail, a former railroad turned public green space that Backpacker magazine named one of the best hiking routes in the country.

Lost World Caverns is another draw. Located 120 feet below ground, the caverns remain a cool 52 degrees year-round. It takes 45 minutes to walk the half-mile cave loop, whose highlights include a 28-foot stalagmite and a 30-ton compound stalactite called the Snowy Chandelier, or you can throw on a headlamp and sign up for a more immersive three- to four-hour guided tour. Also underground: the declassified Cold War bunker at the Greenbrier, a 240-year-old resort in White Sulphur Springs, about 15 minutes from Lewisburg. Ninety-minute daily tours of the once top-secret government fallout shelter are open to the public, although advance reservations are necessary.

In the town of Lewisburg proper, shop for pottery, paintings, and hand-crafted jewelry at WV Fine Artisans and Cooper Gallery; sample handcrafted Appalachian hard cider and dry aged mead made from heirloom apples and wildflower honey at Hawk Knob; and explore the local food scene, where the options run from old-school fancy (escargot at the French Goat, the sister property of Maison Marcel) to lowbrow delicious (chili slaw dogs at Jim’s Drive In).

Time your visit to January 24–25, 2020, to catch 50 bands playing seven venues throughout downtown Lewisburg as part of its eighth annual West Virginia Winter Music Festival. And be sure to check the events calendar at Carnegie Hall before setting out: One of only four Carnegie auditoriums in the world, it hosts Shakespearean theater, jazz pianists, cowboy-themed Christmas shows, and more.

Saranac Lake is located five hours north of New York City and 90 minutes from the Canadian border in New York’s Adirondack region.

Saranac Lake, New York

For more than a century, this 5,242-resident town in the Adirondacks has staged one of the best snow-and-ice festivals in North America. Located five hours north of New York City and 90 minutes from the Canadian border, Saranac Lake is the beguiling host of the 10-day Winter Carnival, which runs from January 31, 2020, through February 9, 2020. The theme changes each year (the upcoming is “Myths and Legends!”), but a celebration of winter sports is always paramount. Highlights include arctic golf, pond hockey, snowshoe softball, ice skating, innertubing, cross-country ski races, and an Ice Palace fun run. (The Ice Palace, by the way, is a life-sized castle carved from frozen water. Pretty spectacular, especially lit up at night.) If that isn’t enough entertainment to get you bundled up like Randy from A Christmas Story, the carnival also puts on two parades with floats, three mega fireworks shows, and a couple of frying pan tosses, which are exactly what they sound like.

Winter Carnival aside, Saranac Lake is worth visiting because it has no shortage of unique diversions: Take a spin on one of 24 hand-carved figurines that represent Adirondack-indigenous animals on the sweet-as-can-be Adirondack Carousel in William Morris Park; sign up for a lantern-lit sleigh ride at Lake Clear Lodge; or tackle approximately 14 miles of cross-country, snowshoeing, and mountain biking trails at Dewey Mountain Recreation Center, 10 of which are groomed and lit for night activities.

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To eat, head to Origin Coffee Company for a cardamom cortado and fancy toast (wild berry jam, Asgaard Farm goat cheese, lime zest, and black pepper on Rock Hill Farm bread), followed by a Frenchified lunch at Left Bank Café and dinner at the casually refined Fiddlehead Bistro, which sources the meat, dairy, and veggies on its ever-changing seasonal menu from regional farms.

To sleep, consider Hotel Saranac from the Curio Collection By Hilton, a newly renovated inn with 78 guest rooms and 24 suites. For those traveling on a more generous budget, there’s the Point, a Gilded Age lodge built by the Rockefellers during the Great Camp Era. Today the 75-acre estate is open as a five-star, adults-only Relais & Châteaux getaway loaded with Old-World charm. From the fine American landscape paintings to the kid-glove service, it’s a throwback unlike any other.

This article originally appeared online in November 2018; it was updated on December 3, 2019, to include current information.

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