Osthoff Resort in Elkhart Lake, Wisconsin.

Osthoff Resort in Elkhart Lake, Wisconsin.

Each year, I always look forward to the New Year. But by the time January and February arrive, I think we're all ready for a break. I want to change my routine and scenery and head for the open road. Before Covid hit we mostly flew everywhere we wanted to visit but, following the pandemic, we have now learned to fully embrace the joys of traveling by car. And, to be honest, my palms get sweaty thinking about flight cancellations and the horrors in general of going to an airport, not to mention my fear of flying.

There's no better way to discover the U.S.A. than on an old-fashioned road trip (aka mini-mental health break). Where else will you find restaurants with names like the Pig Hip Inn (Broadwell, Illinois) or discover fabulous, carnival-like antique malls (Livingston, Illinois), or see the world's largest rocking chair (Casey, Illinois) unless you're taking the roads less traveled?

So, whether you're looking for an old-school dining experience, snowy ski trips, world class art, lakefront retreats or sleigh rides, here are some recommendations for getaways that are not too far away and offer delightful activities for the whole family, even in the dead of winter.

Wisconsin Dells (Located 2 hrs. 52 minutes from Chicago): The "Dells" are located in Wisconsin's Heartland, in the middle of the southern half of the state and feature beautiful rock formations and waterways plus a variety of year-round family-friendly activities. It's also the home of an old fashioned supper club experience that still exists at The Del-Bar Supper Club. Since 1943, this local favorite, located at 800 Wisconsin Dells Parkway, has been serving it up "old school." Besides throwback restaurants, the "Dells" offer indoor water parks (Noah's Ark Waterpark), local wineries and breweries, Christmas Mountain skiing, snowboarding and tubing (through March) and, of course, Asgard Axe Throwing! The rustic Baker's Sunset Bay Resort is a fun choice for lodging (921 Canyon Rd.) and it's pet friendly too!

Red Ridge Ranch Sleigh Ride experience near Baker's Sunset Bay Resort in the Wisconsin Dells.

Red Ridge Ranch Sleigh Ride experience near Baker's Sunset Bay Resort in the Wisconsin Dells.

Indianapolis, IN. (Located 3 hrs., 6 minutes from Chicago): In downtown Indianapolis, don't miss Indy's Bottlework District that offers big city culture in a 12-acre, mixed-use neighborhood. Here, you will find local indie shops in historic industrial buildings like Circle City Industrial Complex, a 500,000 square-foot warehouse in the old Schwitzer car manufacturing facility. Other places worth a visit are Good Neighbor (clothing, gifts, perfumes and more) and the Living Room movie theater. For dinner, head out of the district to Public Greens, a modern, community-driven restaurant (that is also an urban micro-farm) which shares its profits to feed Indy’s under-served youth each week. The Bottleworks Hotel, formerly the world's largest Coca Cola bottling plant, is the place to stay (850 Massachusetts Avenue).

Elkhart Lake, WI. (Located 2 hrs. from Chicago): Wisconsin's charming resort town of Elkhart Lake is also a beautiful winter wonderland with amenities ranging from horse-drawn wagon rides to plentiful shopping, dining and lodging options. The AAA Four Diamond Osthoff Resort sits at the entrance of Elkhart Lake and is the largest of three resorts that share the area (Siebkens Resort, since 1916, and Victorian Village Resort). Foodies will enjoy the L'ecole de la Maison Cooking School (within the Osthoff) and those looking to relax, will love the Aspira Spa.

Casey, IL. (Located 3 hrs. 35 minutes from Chicago): Casey, Illinois, population 2,635, is the Guinness Book of World Records capital of the world with several super-sized items in the form of outdoor sculptures that are included in the record book! Local craftsman and businessman, Jim Bolin, has built fourteen record-qualifying items including the World's Largest Wind Chime, Rocking Chair, Pitchfork, Golf Tee, Yardstick, Wooden Token, Dutch Wooden Shoes, Mailbox, Pencil, Birdcage and more! Unique and Insta-worthy!

World's largest mailbox in Casey, Illinois. You can even mail letters inside! (Photo by Kevin Ramos-Guinness World Records)

World's largest mailbox in Casey, Illinois. You can even mail letters inside! (Photo by Kevin Ramos-Guinness World Records)

Lake Geneva, WI. (Located 1 hr. 28 minutes from Chicago): During the winter, check out the Ice Castles (at Destination Geneva National), an awe-inspiring display of icicles (check availability first). For lodging, first choice, French Country Inn (W4190 West End Rd.), second choice, The Geneva Inn on the Lake (N2009 S. Lakeshore Dr.). In season, don't miss Richardson Adventure Farm in Spring Grove (909 English Prairie Rd.); Ten Chimneys (home of Broadway legends Alfred Lunt and Lynn Fontaine (Genesse Depot, WI); Mars Resort (best Friday night fried walleye, W4098 S. Shore Drive); Anthony's Steakhouse & Seafood, since 1978, an old-fashioned supper club located at W3354 State Rd. 50. or ziplining on a Lake Geneva Canopy Tour. And, for Victorian charm, try the 19th century Baker House hotel on the lake.

Ziplining on a Lake Geneva Canopy Tour.

Ziplining on a Lake Geneva Canopy Tour.

Saugatuck, MI. (Located 2 hrs. 16 minutes from Chicago): Saugatuck offers something fun to do in every season. In winter, enjoy sledding, tubing, skiing or snowshoeing at the Saugatuck Dunes State Park, Oval Beach Trails or Schultz Parks. Off the slopes, warm up with a Michigan-made red wine or dark porter at one of the area's wineries, breweries or cideries. At Virtue Cider in Fennville, you can even take a sleigh ride across the property. Try the small, exclusive Lake Shore Resort with private lake access at 2885 Lakeshore Drive.

Milwaukee, WI. (Located 1 hr. 31 minutes from Chicago): Milwaukee is a city teeming with great museums and great beer. Both the Pabst Brewing Company and Miller Brewing Company call this city home. Visit the acclaimed Milwaukee Public Market in the Historic Third Ward, a revitalized warehouse district; The Milwaukee Public Museum (home to fossils, a butterfly garden, and more); the Harley-Davidson Museum; Lakefront Brewery; Pabst Mansion and the Mitchell Park Horticultural Conservatory. As an homage to the city's rich beer history, be sure to take a Miller Brewery Tour! Stay in the art-filled boutique hotel, Saint Kate Arts Hotel, centrally located at139 E. Kilbourn Ave.

Bottleworks Hotel, formerly the world's largest Coca Cola bottling plant, in Indianapolis, Indiana.

Bottleworks Hotel, formerly the world's largest Coca Cola bottling plant, in Indianapolis, Indiana.

Geneva, IL. (Located 54 minutes from Chicago): Geneva, Illinois, a perfect destination for people looking for a small town getaway. Wander the city, check out the murals and outdoor sculptures, shop the many antique stores and browse local, independent shops selling a variety of home goods and specialty foods. For an elegant and atmospheric spot to stay, try The Herrington Inn & Spa, right on the Fox River, at 15 S. River Lane.

Harbor Country, MI. (Located 1 hr. 15 minutes from Chicago): Take your pick of the eight charming lakefront towns known as Harbor Country, Michiana, Grand Beach, New Buffalo, Union Pier, Lakeside, Harbert, Sawyer and Three Oaks. Besides the usual winter activities like cross-country skiing, snowboarding and sledding, the restaurants scattered throughout these towns make it worth a visit too. In New Buffalo, pop in for a burger at Stray Dog Bar & Grill. In Union Pier, grab dinner at Timothy's where the kiddos will have fun trying to spot the "moving tree." For unique lodging, stay in the rustic cottages at the Firefly Resort near the beach (built in the 30s, 15657 Lakeshore Road, Union Pier).

Kohler, WI. (Located 2 hrs. from Chicago): Enroute to Kohler, make sure to pop in at the Mars Cheese Castle, a specialty food store in Kenosha described as a "cheese landmark." In Kohler, head to the classic hotel, the American Club, where you can experience Destination Kohler (and its famous Kohler Waters Spa) as well as outdoor adventures at the River Wildlife preserve, a 500-acre wilderness playground. Try cross-country skiing through rolling trails, ice skating and curling at Winter Wonderland and fireside dining at the River Wildlife Lodge, the preserve's charming log cabin outpost.

(This article has been updated from the original on 12-18-23)

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