Three Charming Midwest Destinations to Book Now for Festive Holiday Cheer

Oct 16, 2025

We’re not trying to rush through Autumn by any means, but now is definitely the time to book your holiday festivities and getaways. Thinking ahead for those holiday celebrations can save you a lot of stress, and secure your spot before they book up fully. On today’s blog, we’re fast forwarding a bit to winter holiday getaways that you can book today. We’ve got three spectacular family-friendly destinations serving up that home-away-from-home experience for the holidays. From brunches with the big-man himself to seasonal crafting classes to special brunch reservations, you’ll find that early holiday planning will be in your favor! Once you’ve got those bookings made, you can get right back to those spooky costume parties and planning your Thanksgiving menus.

So, what are you waiting for? Hop in your new car from Classic in Waukegan and let’s hit those snowy roads to winter holiday fun! (In two months, that is!)

Santa Claus, Indiana is fondly known as “America’s Christmas Hometown”, and with good reason! This charming small town offers both Indiana and the US’s first themed attraction, Santa’s Candy Castle, opened in 1935. In 1936, Santa Claus Town expanded with the addition of Santa’s Workshop and the Toy Village! Starting Thanksgiving weekend, things begin to jingle and twinkle with pure holiday magic: Santa Claus Land of Lights at Sun Outdoors Lake Rudolph is a local festive favorite; the Live Reindeer make an appearance at Santa’s Toys; the Santa Claus Arts & Crafts Show offers holiday gift shopping and artisan made goods; Santa storytime at Santa Claus Museum and village; Christmas in Dale’s Light Show is open, enjoy Candlelight evenings on the Farm, Christmas Dinners and Breakfasts with Santa; the annual Santa Claus Christmas parade, and a whole lot more!

Santa’s Candy Castle is open for visits and offers a whimsical blend of historic old-world charm with modern-day fun and games. Enjoy a selection of vintage, old-fashioned candy, 35 different flavors of hot cocoa, frozen hot chocolates, and more. Santa’s Toys offers a selection of nearly 3,000 different toys and games for all ages. Evergreen Boutique and Christmas Shop offers an assortment of gorgeous clothing, accessories, and jewelry, plus one-of-a-kind holiday items and home decor such as candles, ornaments, tree trimmings, and more. Several local hotels and motels in the area continue the holiday and Santa Claus theme with cozy winter accommodations, too.

Frankenmuth, Michigan is better known as “Little Bavaria”, really leans into the magical holiday spirit full force in its mere 2 square miles. From mid-November, Main Street explodes with festive joy as more than 150 decorated, sparkling lit trees line the street. You’ll find Christmas and holiday decorations in each storefront, colorful light displays of seasonal cheer and famous characters, and more. And it’s all culminating at the center of town in a 40-foot Christmas tree featuring 23,000 synchronized lights for a 7-minute long light-and-music show for the holidays.

Bronner’s Christmas Wonderland spreads across 5 acres of different Christmas tree trims, gift options, ornaments, and more; while you’re there, be sure to check out the Silent Night Memorial Chapel, a recreation of the chapel in Obendorf, Austria, where the song “Silent Night” was first performed. Be sure to check out Christmas Lane in the evening when you’re done shopping for a brightly lit and festively decorated road that bursts into Christmas joy when the sun goes down. Grandpa Tiny’s Farm is a historic working farm located just across the street from Bronners. Each year in December, the farm puts on weekend Christmas experiences including 2 special guest reindeer visitors! The Frankenmuth Ice Rink also returns annually to Zehnder Park in the center of town and is open all week long to the public. Be sure to check out the full Christmas itinerary on the town’s local seasonal calendar!

Elkhart Lake, Wisconsin is a rockin’ good time during the holiday season. This cozy town features storybook level charm with twinkling lights, wholesome decorations, and plenty of holiday spirit. Enjoy the Old World Christmas Market which is open daily from 10AM to 5PM starting December 5th through the 14th, now in its 26th year, featuring artisanal goods and handmade gifts. Book a special holiday brunch with real live reindeers, a breakfast with St Nick Himself, or a Christmas Day Brunch for an extra special family memory. The Hard Left Lounge will be hosting special holiday spirits and libations starting in November, creating a warm and friendly holiday atmosphere and cozy retreat from holiday hecticness. The Pankratz Arts Exchange hosts their annual winter show at The Theater at the Shore Club featuring classic holiday favorites and cheer. Nearly a dozen local shops are also offering extended retail hours and hosting their 14th Annual Holiday Open House on December 6th from 12PM-4PM. For families, you won’t want to miss festive events like “America’s Christmas Tree Lighting” on December 4th, Cookie Decorating and Ornament/Stocking Decorating for Kids on December 6th and 13th, Horse Drawn Wagon Rides on December 6th, 13th, and 24th, and more! For adults, don’t miss Ole Smoky Christmas Cocktail Class on December 4th, the Sip and Spruce event on December 5th, Naughty but Nice Christmas Cocktails on December 12th, and more.