The Midwest is known for its warm hospitality and seasonal festivities. So, it’s no surprise that some of our favorite communities transform into jaw-dropping scenes of lights, markets, and holiday cheer this season. And best of all? While countless visitors love strolling the historic streets of Galena, Illinois, or experiencing the unique year-round Christmas celebration in Santa Claus, Indiana, these towns aren’t just vacation spots. They’re also vibrant communities, ideal for people looking for a small town to call home.
No matter which holiday you celebrate, if you’re looking to get out and explore some quintessential Midwest towns this season, we’ve rounded up some of our favorite winter wonderlands. Each of these towns celebrates the holidays uniquely and offers distinctive living experiences, whether it’s your primary home or weekend go-to.
Galena, IL: A Historical Holiday Getaway
Image credit: Visitgalena.com
Take one trip to Galena at this time of year, and you’ll see why Midwest Living recently named it one of the top holiday shopping destinations. Galena’s well-preserved 19th-century buildings and cobblestone streets are the ultimate trip back in time. The town is aglow in December with holiday lights, with especially amazing displays lining Main Street.
While here, visit the Night of the Luminaria for a stunning display of over 5,000 candle-lit luminaries. From there, explore the local shops – more than 100 in downtown Galena alone, including bookstores, gift shops, and high-end cooking accessory shops. Afterward, grab a bite at the historic Log Cabin Steakhouse and stay at the cozy DeSoto House Hotel.
And if you’re here in early December? Don’t miss the annual holiday parade along with the Holidaze Festival.
Resident Insights: Galena is a popular second-home destination for Chicagoans. During your next visit, check out the town’s historic homes, particularly those near Main Street. These houses are highly sought after, offering a blend of vintage charm and modern comforts that give them broad appeal among buyers.
New Glarus, WI: A Swiss-style Holiday Retreat
Image credit: Fabulous Wisconsin
New Glarus, located about a half hour southwest of Madison, proudly preserves its Swiss heritage, reflected in its architecture and customs. This heritage comes alive during the holiday season with Swiss-inspired decorations and plenty of festivities for all ages.
If you’re planning a trip to New Glarus, check out the Swiss Christmas Market for artisan crafts and traditional Swiss treats. Plan to visit in early December to check out the annual tree lighting.
After a long day of shopping and snacking, settle down for a meal at Glarner Stube, which serves classic dishes, including its house fondue menu. Once you’ve filled your melted cheese quota, check into Chalet Landhaus Inn for a truly authentic Swiss experience.
Of course, no trip to New Glarus is complete without a visit to New Glarus Brewing Co., the local brewery that’s famous for selling its beers in Wisconsin and Wisconsin only. Many an Illinois resident has made a run for the border to pick up a case or two of Spotted Cow, but during the holidays, you might be tempted to try one of New Glarus’ seasonal brews like Fat Squirrel Nut Brown Ale or Edel-Pils German Pilsner.
Resident Insights: “America’s Little Switzerland” offers a European living experience, with quaint, chalet-style homes popular among buyers. Established as a Swiss Colony in 1845, the town has retained its Alpine-style architecture, cultural festivals, and Swiss shops, restaurants, and experiences. And it’s all just 28 miles south of Madison.
Santa Claus, IN: Christmas All Year Round
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Originally established as Santa Fe, the town was forced to change its name in 1856 when the Post Office Department informed residents that they would no longer deliver mail because there already was a Santa Fe in Indiana. A vote was held and Santa Claus emerged the winner. Over the years, Santa Claus has transformed into a year-round Christmas-themed town, complete with street names and businesses reflecting the town’s unwavering holiday spirit.
If you plan a December visit, swing through the Santa Claus Museum & Village. And don’t miss the three-week-long Santa Claus Christmas Celebration, a town-wide event with parades and festive activities.
Before heading home, enjoy a meal at the festive Santa’s Lodge. Even if you don’t visit during the holidays, this landmark is a must-try, offering holiday-themed dining year-round. Opt to stay over, and you can dip in their indoor or outdoor pools or try catch-and-release fishing, weather permitting.
Resident Insights: The town’s unique theme makes it an attractive spot for those seeking a friendly, festive atmosphere year-round. With fewer than 3,000 residents, Santa Claus has a small-town, rural vibe, with highly-rated public schools.
Some additional towns topping our holiday travel wish list?
Home to Bronner’s Christmas Wonderland, enjoy traditional German fare at the Bavarian Inn Restaurant. Real estate here offers a blend of traditional German-style architecture and modern homes.
Visit the Shipshewana Light Parade and enjoy Amish cuisine at the Blue Gate Restaurant. The local housing market is known for its rural charm and spacious properties.