American Cities and Towns With the Most Holiday Spirit

Johnny Johnston has lived in Los Angeles for 20 years, but when he goes home for the holidays, he finds himself enchanted all over again by the winter wonderland where he grew up: Vail, CO.

“From the moment you drive into the valley, the streets and public spaces are all lit with Christmas lights, creating a Norman Rockwell moment,” says the broker for Sotheby’s International Realty. Even if his mom still hassles him about what shirt he wears to his aunt’s dinner party, “Vail is the most beautiful place I’ve ever seen for the holiday season.”

Many Travel + Leisure readers agree, ranking the Colorado mountain town at No. 2 for seasonal cheer in the America’s Favorite Places survey. Readers evaluated hundreds of towns in dozens of features, from romance to thriving art scenes to irresistible bakeries. To determine the best towns for the holidays, we combined the scores in a few festive categories: department-store shopping, notable restaurants, and Christmas lights.

Plenty of the top 25 holiday towns offer creative spins on holiday traditions, too, whether they look like winter wonderlands or not. In a South Carolina town, you can have your turkey dinner in barbecue sauce. In one mountain town, the annual tree lighting involves a faux pine made of recycled skis. And in places from Healdsburg, CA, to Charlottesville, VA, you can pick up holiday gifts—local wines, French linens, or antique cookbooks—that you’d never find at the mall back home.

Another kind of holiday magic (low-season rates and fewer crowds) can create a blissful version of Silent Night. That’s why Far Hills, NJ, resident Gavin Macomber has spent a few Christmases by the beach in Nantucket, MA. “It’s fun to walk around town sipping hot chocolate and watching snow fall,” says the founder of Andegavia Cask Wines. “Nantucket is particularly peaceful this time of year—which makes it an ideal place to escape to during the holidays.”

No. 1 Aspen, CO

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 Cristal New Year’s Eve Party.

No. 2 Vail, CO

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.

No. 3 Ogunquit, ME

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.

No. 4 Nantucket, MA

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. Nantucket also scored well with readers for feeling both mellow and romantic.

No. 5 Naples, FL

This Florida town lacks snowman-building material—it ranked highly in the survey for warm weather and beach getaways. But the snowbird-style winter wonderland still lured 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.

Read the full list HERE.

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