7 Merry Cities to Spend Christmas

From Boston’s cobblestoned streets to Taos’ paper lanterns, these are the country’s most festive cities

Photo Sasabune Omakase Modified: Flickr/erin/CC 4.0

Whether you’re getting away from your family or visiting your relatives, Christmas travel is all about finding that warm and fuzzy feeling of snuggling by a fireplace, listening to carols, and exchanging carefully considered gifts. But not all destinations are created equal when it comes to twinkling lights, sweet shop windows, and the general jolly spirit of the season. Some cities really come into their own around the holidays, with festive details big and small that visitors and locals savor.



The historic cobblestoned streets and heaps of New England charm play in Boston’s favor over the holiday season. Holiday markets sell local artisans’ works; restaurants with cozy fireplaces serve classic, hearty roasts (or roasted lobster) and holiday dinners; and families can warm up with hot chocolate after ice-skating on Frog Pond.

Stay: XV Beacon is one of Boston’s most modern and charming boutique hotels and it puts you within steps of the classic cobblestoned streets of Beacon Hill, where cute cafés are only outnumbered by local boutiques. 

Eat: Spend Christmas Eve at the sleek Bistro du Midi, indulging in a Provençal menu of Christmas-inspired dishes.

Play: Skating on Boston Common’s Frog Pond is fabulous Boston fun, take the kids to Boston Ballet’s production of "The Nutcracker," or join in the candlelit carol singing at Trinity Church.


From the Christmas tree in Daley Plaza to the brightly lit and wildly decorated holiday train, Chicagoans play on all aspects of the Christmas spirit. The lights on the Magnificent Mile, snowy trips for pretzels and hot mulled wine at the city’s huge Christmas market, and ice-skating in Millenium Park make for high-energy holiday activities. (Photo courtesy of Flickr/Marit & Toomas Hinnosaar)

Stay: The Sax Chicago, right on the Chicago River, has a fun and whimsical design, with romantic touches and bold colors throughout. The hotel’s restaurant, Bin 36, is a chic and relaxed watering hole that serves as breakfast spot, wine and cheese bar, and cocktail lounge.

Eat: Sink into a red leather armchair and settle in for your Christmas steak at Drake Bros in the Drake Hotel.

Play: Bring the kids to Navy Pier’s Winter WonderFest, complete with rides, a huge Christmas tree, and live music, and stare out at the giant tree while last-minute shopping at Macy’s.

Park City, Utah

Find the ultimate white Christmas in Park City, Utah, where Main Street looks out onto snowcapped mountains and days are spent skiing the slopes. Stroll down Main Street, popping into little boutiques, and join the annual Torchlight Parade on Christmas Eve.

Stay: Spring for a luxe holiday getaway at the Montage Deer Valley, where your hardest decisions will be whether to ski or après-ski.

Eat: Sneak into a cozy table at Canyons Resort’s Alpine House for comforting holiday fare and a long list of wines, like robust reds that pair well with the snowy mountain outside.  

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Play: Zip up that red velour suit, because every December the city hosts a Santas Ski Free day. Or watch as a lone (hired) Santa Claus skis the slopes himself before delivering treats to kids.