Celebrate the Holiday Season in One of These Festive Spots

From Thanksgiving through the new year, you’ll discover that Nantucket, Chicago, New Orleans and Breckenridge are brimming with holiday cheer.

by NEA Member Benefits


Nantucket, Massachusetts

Winter is the quiet season on Nantucket, when islanders revel in sweet, time-honored traditions. The holiday fun begins with a jolt on Thanksgiving morning, with the Cold Turkey Plunge into the bracing waters of the Atlantic at Children’s Beach.

Holiday decorations reflect this New England island’s maritime heritage. A large wreath graces the Brandt Point Lighthouse, trees sprout from the bows of boats, and strings of lights illuminate sailboat masts. The Nantucket Historical Association Whaling Museum displays dozens of decorated evergreens at its Festival of Trees.

Nantucket’s holiday highlight is the annual Christmas Stroll weekend (taking place November 30 - December 2 in 2018). It seems everyone on the island wanders the downtown cobblestone streets, which are filled with decorated storefronts and Victorian carolers. A town crier announces the arrival of Santa Claus—by Coast Guard cutter!

Chicago, Illinois

The Second City is second to none when it comes to holiday revelry. On Thanksgiving morning, thousands of spectators line State Street for the McDonald’s Thanksgiving Day Parade. Large inflatable balloon characters, decorated floats and marching bands highlight the event, an annual tradition since the Great Depression.


Downtown’s Daley Plaza hosts Christkindlmarket, the largest open-air German Christmas market outside Europe. It features market stalls selling holiday ornaments, toys, food and other gifts, along with live entertainment by choirs and bands. The Magnificent Mile Lights Festival kicks off the holiday season with a festive lights display and parade that brightens one of the city’s key shopping districts along Michigan Avenue.

Along the Lake Michigan waterfront, Navy Pier celebrates the season with Winter WonderFest, an enormous indoor winter playground filling a 170,000-square-foot arena. It’s a heady mix of holiday decorations and kid-pleasing attractions, including a skating rink, carnival rides, North Pole scenes and visits with Santa.

New Orleans, Louisiana

No city knows more about celebrating than the Big Easy. In November and December, visitors enjoy a busy roster of holiday events along with mild weather and some of the best hotel rates of the year. On Thanksgiving, you’ll find special dinner menus at many restaurants. Here’s your chance to try that Cajun specialty, a turducken: a turkey stuffed with a duck stuffed with a chicken.


More than 1 million lights illuminate the moss-draped cypress and live oaks in City Park during the holidays. Celebration in the Oaks activities include a 2-mile train ride through the lights and the animated “The Cajun Night Before Christmas” display.

Holiday decorations also festoon the French Quarter, downtown streetcars and the Riverwalk shopping district along the Mississippi. Elegant historic homes of the Garden District and French Quarter open their doors in December for holiday home tours. It’s a rare chance to peek inside these antebellum charmers, decked out in holiday finery.

Breckenridge, Colorado

Dreaming of a white Christmas? The odds are good in this mountain resort community, which sits high in the Colorado Rockies at 9,600 feet. The historic gold and silver mining town 80 miles west of Denver looks more picturesque than ever during the holidays. Opening day of the Breckenridge Ski Resort, usually in mid-November, kicks off the holiday celebrations here.

On the first weekend in December, hundreds of Santas race down Breckenridge’s Main Street, followed by a Bernese Mountain Dog parade, the arrival of Santa Claus by horse-drawn carriage and the lighting of the town tree. The Breckenridge Arts District hosts a Handmade Holiday Market, with music, artists’ demonstrations and a variety of craft items priced at $50 or less for holiday shopping.

Breckenridge rings in the New Year with activities in town and on the mountain. The “glow worm parade” kicks off the evening, with kids ages 5-13 skiing down a beginner slope with glow sticks. Then comes the long-standing torchlight parade down the ski slopes, along with parties in town and fireworks visible from the Blue River Plaza. Early risers on New Year’s Day often can enjoy uncrowded slopes.

Plan your holiday getaway today