America’s Best Towns for the Holidays

A combination of luxe living and quaint charm helped this Rocky Mountain town capture the spot as the merriest of them all. Wandering along Cooper Avenue, you may chance upon cookie exchanges, public s’mores roasts, or elf meet-and-greets. But the two most famous hotels in town act as the nerve centers for holiday cheer. The lobby of the Hotel Jerome regularly hosts carolers, while the Ajax Tavern and Element 47 at the Little Nell both serve fabulous holiday meals, with indulgences like venison loin with huckleberries, black truffles, and chestnut-and-caramel profiteroles. The Little Nell also hosts the all-you-can-sip Bottomless Dom Perignon New Year’s Eve Party.

Ski season kicks into high gear during the holidays in this Colorado wonderland. December brings the festivities of Snowdaze—where the fresh powder is celebrated with live concerts every evening—and Holidaze, which includes the village’s tree lighting during the winter solstice and a New Year’s Eve torchlight parade down Golden Peak, followed by fireworks. Any time of year, readers love Vail’s liquid nourishments, ranking the town highly for its hot coffee (compare local favorites Yeti’s Grind and Loaded Joe’s) and equally warming cocktails. You might toast the New Year with a Rosemary Lemon Drop (rosemary-infused vodka with lemon juice and a sugar rim) at the icicle-decorated bar Frost, inside the recently renovated Sebastian Vail.

Readers may be drawn to this former artists’ colony in Maine as a beach getaway, but the holiday season brings the perks of winter on the sand: lower prices and overall calm, with just enough festivity to keep things humming. Mid-December’s Christmas by the Sea Festival typically includes a bonfire on the beach and a soul-warming chowder fest. From Ogunquit, you can also easily reach two shopping areas for getting through your list: the Kittery Outlets and, an hour away, Freeport. For distinctive local shopping, browse the Harbor Candy Shop, where the gift boxes include a Vegan Sampler, featuring soy truffles, marzipan, and orange peel enrobed in dark chocolate.

The banner event during the holidays in this island town started in the 1970s, because too many locals left to shop in Cape Cod. Today, during the annual Christmas Stroll—typically the first weekend in December—you can shop downtown amid dozens of seven-foot, decorated Christmas trees, and take part in wine tastings, ghost walks, and home tours. Pick up some gifts at Murray’s Toggery Shop (the mother ship for holiday-ready Nantucket Reds pants) and Jessica Hicks, the boutique of a local jewelry designer. For more tree-gazing, go to the Whaling Museum, which houses 80 trees decorated by local artists, merchants, and kids. 

This Florida town lacks snowman-building material, but the snowbird-style winter wonderland still lures holiday revelers with its luxury stores, cool boutiques, and festive ambience. Third Street South is the headquarters for the official tree, evening “snow” showers during Thanksgiving week, and gorgeous window displays, like those at department store Marissa Collections in the Old Naples Historic District. Continue shopping along Fifth Avenue South, and check out whimsical clothing and gift shop Wind in the Willows, whose window won Best in Show at the 2013 local holiday decorating contest. Of course, the holidays are about more than retail; catch the Naples edition of the worldwide TUBA Christmas, a concert on Fifth Avenue South’s Sugden Plaza featuring brass tubas, euphoniums, and baritones.

Breckenridge gets revved up during the holidays, as ski season swings into high gear. Indeed, this resort town skates the fine line between thrills and low stress, ranking well in the survey for both adventure and safety. On the first weekend in December, the traditional lighting of the town’s official tree coincides with the Running of the Santas, in which hundreds of red-clad, supersize elves take to the streets; on December 31, there’s a torchlight parade down the mountain, followed by fireworks. Readers also loved the après-ski watering holes, from the house-made brews at Breckenridge Brewing to the martinis and flights of Colorado beers at Base 9 Bar.

Grande dame hotel The Greenbrier is the epicenter of the holidays in the Lewisburg area. The 18th-century resort trims the lobby with opulent decorations, holds ribbon-tying seminars in its Christmas Shop, and offers weekday discounts on treatments at its legendary mineral-springs spa. While you can hear the West Virginia Symphony play at Lewisburg’s own Carnegie Hall, the town may otherwise win the Silent Night award, getting high marks for peace and quiet. 

Winter weather doesn’t really kick in until January in this Outer Banks town, so the holiday season is typically still a good time to paddle a kayak or take a boat tour along Taylor’s Creek. The Christmas lights take to the water too: one of the biggest holiday events is the Crystal Coast Christmas Flotilla, a twinkling-lights-strewn boat parade held on the first weekend in December. Readers’ favorite cuisine in this low-key town are the sandwiches: try the double crab cake Cranky Crab at the Beaufort Grocery.

This California town with a rocky coastline doesn’t experience much in the way of winter, but the chilly air makes the crashing waves and neighboring wine country seem all the more enticing. Carmel has its own tree lighting—a huge resident tree at the corner of Junipero and Ocean avenues—and the quiet days of early December also make it a little easier to get a table at nearby restaurants like La Bicyclette and Flying Fish Grill. December also brings the Inns of Distinction Tour, which includes the Cypress Inn (dating back to 1929) and the cottage-style Wayside Inn, as well as wineries such as Heller Estate and Cima Collina. Carmel also ranked well for its distinctive shopping; pick up French linens and antiques at Jan de Luz.

The holiday season ushers in serious wattage—star-powered and otherwise—in this Utah mountain town. In late November, Park City holds its annual Electric Parade, in which locals light up their trucks, cars, and bicycles and crank up the holiday tunes as they parade down Main Street. On Christmas Eve, Saint Nick spends the day skiing the slopes and then leads a torchlight parade down the PayDay trail. January’s Sundance Film Festival draws a Hollywood crowd, yet Park City also scored well with readers for feeling family-friendly. During the holidays, kids and sweet tooths of all ages will love the life-size gingerbread house (nearly 13 feet tall, made with 11,000 cookies) at Montage Deer Valley.

The holiday season coincides with the kickoff of high season in this northwest Florida town, which also ranked well for beach vacations, family getaways, and boutiques. So it’s a good place to browse for notable gifts, from the heirloom-quality porcelain at Santa Rosa Pottery to the pre–World War I cookbooks at Kitchen Garden Books & Antiques. Folks who don’t want to put on holiday pounds might consider the 40-mile Winter Solstice Run, which begins in Santa Rosa at dawn on December 19, 2015, and goes along beaches, lakes, and through state forests (good news: there are also shorter versions and a relay). Luckily, the town also boasts year-round running weather.

Late fall and early winter are a good time to score lower rates in this family-friendly town, but that doesn’t mean that the place has gone totally quiet. Showstoppers around Myrtle Beach include the twinkling Christmas trees and 5,500 hand-lit candles at Brookgreen Gardens as well as the Festival of Trees—with themed trees for all 50 states—at Ripley’s Aquarium. Readers had a weakness for Carolina barbecue in this classic-boardwalk beach town: you can stay true to the season by ordering barbecued turkey at Waterscapes, in the Marina Inn at Grande Dunes, where the bird is lovingly slathered with the mustard-accented, South Carolina–style sauce.

History-rich Williamsburg, where tricornered hats count as timeless fashion, scored highly for colorful people-watching. This time of year also offers plenty of events that let you experience a holiday season like the colonists would: in Jamestown you can watch as wild turkeys are roasted and puddings are prepared, and see how settlers may have observed Christmas (including a few long-gone English traditions like an anti-Santa called Lord of Misrule). Readers’ favorite meal around here was brunch: try the Virginia ham and biscuits, with the Special Rebel Cocktail (tomato juice, beer, and spices), at the Old Chickahominy House.

If a flashing-neon-colored holiday makes you cringe, head to this tony town in Rhode Island, where only white lights are encouraged on homes and restaurants, to conjure an old-fashioned candlelit vibe. Touching on its upper-crust history, the Mansions of Newport Tour takes you on a stroll through Gilded Age icons like The Breakers, the Elms, and the Marbles, all decked out in sumptuous trees, fine china, and decorations. Since crowds are lighter, it’s a good time to try Newport’s high-ranking restaurants like the locally sourced Tallulah on Thames; every Sunday during winter it offers a three-course, prix fixe Family Dinner Night.

This military town along the Chesapeake Bay does plenty of pomp, circumstance, and tailgating during the holiday season. Annapolis ranked well for Christmas lights, notably the drive-through Lights on the Bay in Sandy Point State Park, which starts up in mid-November. Downtown Annapolis also keeps its shops lit and open until midnight on a few Thursdays during December. To celebrate alongside the military locals, you can hear Handel’s Messiah performed by the Naval Academy Glee Club in the Naval Academy Chapel, or just sit tight until the Military Bowl, which comes every yaer in late December, at the U.S. Navy–Marine Corps Memorial Stadium. No surprise, the locals also scored well for being passionate sports fans.

Forget green: the prime holiday color in this Central Coast town is red, as in Pinot Noirs, Cabernets, and Syrahs. During the holidays, wineries offer low-key tastings, music performances, and great gift opportunities; check out Parrish Family Vineyard, whose tasting room is a short walk from downtown’s City Park. Mid-December also brings the many-blocks-long Vine Street Victorian Showcase, with open houses, floats, and carolers amid the decorated historic homes. For some seasonal house envy, go to Hearst Castle, about an hour away, which will be adorned much as it might have been for former resident William Randolph Hearst.

Locals in this quaint Sonoma County town struck readers as brainy, literary types—and one of their biggest holiday traditions is the beloved Dickens Dinners at the Madrona Manor, featuring lobster shepherd’s pie and Christmas puddings that would make even Scrooge smile. Continue feasting during the Wine Country Walking Tours’ four-hour Holidays in Healdsburg tour, where you explore downtown shops and wineries, nibbling on freshly baked artisan breads, juniper honey, and handmade chocolates. For gourmet gifts, pick up kitchen gadgets and locally sourced foodstuffs at Healdsburg Shed.

Telluride scored highly for being pleasantly quirky, and that flair comes through clearly this time of year. The town’s big tree lighting happens on the Ski Tree, made totally of old skis, and accompanies a bonfire comprising more old-and-broken skis. On New Year’s Eve, you can watch more than a hundred ski instructors do a zigzag-patterned torchlight parade down the mountain. Year round, T+L readers loved the local nightlife. Go barhopping from Hotel Madeline’s sleek SMAK Bar to New Sheridan Hotel’s Historic Bar, which has kept the same mahogany-paneled look since 1895.

Bundling up for the holidays in this San Diego enclave means wearing a wetsuit when you surf or stand-up paddleboard—or, on land, perhaps adding a scarf to your ensemble. Indeed, the locals were rated attractive and stylish, and the area offers both high-end and beachy shopping options. The best dining comes with plenty of cheer. Farm-to-table pioneer A.R. Valentien, in the Arts and Crafts–style Lodge at Torrey Pines, hosts Thursday evening Artisan Dinners during the holidays, where you can sit at communal tables and pass plates of seasonal game, wild mushrooms, and locally sourced goodies like a pecan-and-persimmon brioche bread pudding.

This waterfront New England town is steeped in history, with settlements dating back to the 1600s. Winter’s a festive time to explore its 10-acre time capsule, the Strawberry Banke Museum: during December you can skate on its open-air Puddle Dock Pond, or walk the candle-box-lined paths to see decorated homes from centuries past. Portsmouth offers one big 21st-century draw, too: tax-free shopping statewide. Load up on classic toys and kids’ books at downtown’s G. Willikers!

This Jersey Shore town has a strong Victorian streak—its easily recognized by its quaint architecture—and the holiday season pushes it a little further on the Dickensian scale. The walkable Washington Street Mall gets draped in greenery and hosts its annual Hospitality Nights, when merchants hand out treats (in 2015, December 10–11). Angle for samples from the Original Fudge Kitchen, which also offers great fudge-and-saltwater-taffy gift boxes. If you have kids, check in to Congress Hall, where the Grand Lawn across from the beach turns into a beachy winter wonderland complete with a train, concerts, gingerbread decorating, and breakfast or brunch with Santa. 

During the holiday season, Charlottesville quiets down, as college students cram for finals and then head home. Any visitors get the perk of experiencing the Holiday Evening Tours of Jefferson’s Monticello. Charlottesville scores points for its cool, gift-friendly bookstores like downtown’s New Dominion Bookshop, the oldest indie bookstore in the state, and the used-book gold mine Read It Again, Sam. Readers also rated the town well for its local wineries; King Family Vineyards sells gift-wrapped bottles of Cabernet Franc.  

A casino and boardwalk don’t exactly conjure images of plum puddings and carolers, yet T+L readers appreciate Atlantic City’s wild weekend spirit and vivid people-watching. Festivities this year include the Running of the Santas pub run and come to a peak at New Year’s Eve; the biggest party may be at the Crystal Room in the sleek Chelsea, the town’s first non-casino hotel to open in decades.

If holiday stress takes much of the joy out of your world, this quaint wine-country town offers the ultimate antidote: it ranked near the top for spa vacations. Willow Stream Spa at the Fairmont Sonoma Mission Inn & Spa, for instance, does seasonal treatments like the balancing Harvest Kur mud wrap and body treatment, with grapeseed oil, as well as a beta-carotene-rich Pumpkin Enzyme Facial, which promises to minimize lines. While you’re shopping around the town’s plaza for relatives back home, you can admire the holiday window displays, then check out the civilized bottles of olive oil and rare artisanal cheeses at gourmet food market Epicurean Connection.

There’s no chance of a white Christmas in this mild-weathered Orange County beach town. Instead of watching the sky for snowflakes, you can scan the waves for migrating whales—or focus your attention on the holiday series of champagne, spirits, and pastry tastings at the Montage Laguna Beach. The gallery-lined town ranks well for its art scene, and the holiday season brings the Sawdust Winter Fantasy, an arts and crafts festival that spans five weekends in November and December; the little village complex with sawdust-covered paths offers jewelry, blown glass, woodwork, and paintings, as well as a petting zoo and Santa sightings.