Can’t Miss Scenic Stops in Wisconsin and Illinois for Cold Weather Trips

Nov 12, 2021

With the blustery winds of late Autumn ushering in a cold front, we thought it might be nice to give you something to look forward to this Winter! We’re sharing a great list of can’t miss scenic destinations to visit in the Late Autumn and the Winter. Pile on into your new car from Classic and bust through your cold-weather cabin fever!

Our list is chock full of memorable sites to visit and beautiful scenery. So let’s hit the road and liven up those winter blues, because this is most certainly drive-over country!

Cool Places to Visit in Wisconsin & Illinois As Weather Gets Colder

Twelfth Night Holiday Tree Bonfire; Pleasant Prairie WI

20 Miles from Classic Car Dealerships

This historic village tradition takes place every January at Park Drive in Pleasant Prairie. The upcoming year’s event will be on January 6th 2022 at 6PM. Everyone in the village takes down their trees and participates in a community tree burning. There will be hot chocolate and holiday caroling! Just a short drive away with some beautiful scenic lakeside views in the evening.

Wilmot Mountain; Kenosha, WI

30 Miles from Classic Car Dealerships

Grab a season pass now to ensure an exciting time all winter long! Beautiful mountain views, wintersports, snowshoeing, skiing, and special events galore at the Wilmot Mountain resort. Great for weekend getaways or day trips! It’s got gorgeous views and scenery so you’ll want to bring a camera for sure.

Winterfest; Lake Geneva WI
45 Miles from Classic Car Dealerships

Lake Geneva is gorgeous any time of year, but Winter is especially beautiful. Stop by on December 4th and attend the 46th Annual Electric Christmas Parade. Or plan a winter getaway for the family to Winterfest 2022 in February; would be a great holiday gift alternative! Winterfest is home to the only US National Snow Sculpting Championship and it’s chock full of talented artists who sculpt the ice and snow in magnificent forms. And there’s lots of fun to be had on the beach such as bonfires, s’mores roasting, and hot cocoa! You might even want to try a hovercraft ride if you’re feeling brave.

Ice Skating at Edgewater Skating Rink; Madison WI

128 Miles from Classic Car Dealerships

Located on Lake Mendota, this beautiful skating rink has lakeside views and the twinkling skyline of Wisconsin’s State Capitol. The rink hosts special events and themed skate nights throughout the season. Enjoy family skating events and take plenty of memorable photos. A trip here would be a great option for a holiday gift excursion instead of going with Big Box Retail gift items.

Snowtubing at Cascade Mountain; Portage WI
153 Miles from Classic Car Dealerships

There’s nothing more fun than sliding down a pile of snow at warp speed, laughing all the way down as you relive childhood bliss! Gather your friends and family and enjoy a fun filled afternoon of snowtubing and other winter sports at Cascade Mountain. Enjoy the gorgeous mountain scenery along the way!

Garden of Lights; Green Bay WI

172 Miles from Classic Car Dealerships

Just because the leaves have fallen and the temps are dropping doesn’t mean you can’t still have a blast at the Botanical Gardens! More than 300,000 twinkling lights compose the exquisite displays of nature-inspired light and sculpture at the Garden of Lights experience. Enjoy a walking tour or a Horse-Drawn Wagon experience. A perfect gift for the whole family if you’re going the “giving an experience” route over toys or goodies.

Winterfest Sled Dog Race; Merrill WI
255 Miles from Classic Car Dealerships

With over 100 sled dog teams competing in past races, this is a great event for all ages to attend. The race awards prizes for the Top 6 competitors. You’ll find lots of other family friendly activities all weekend long, and even try your hand at some of the kid-friendly mini races! Events will be announced by the Merrill Chamber of Commerce as it gets closer to January/February.

Wisconsin Great Northern Railroad; Trego WI

377 Miles from Classic Car Dealerships

This scenic 15-mile stretch of track runs along the Namekagon River and boasts some truly stunning views. Book the bed-and-breakfast ride or a dinner excursion for a truly unique and unforgettable experience. Fun for all ages and great for groups! Would make a lovely family or friends trip for the holidays, or even a romantic date-night experience.

The Ice Caves; Apostle Island National Lakeshore

420 Miles from Classic Car Dealerships

These stunning ice caves are located in the Meyers Beach area of the Lakeshore region. The Ice Caves are only open during certain times of the year, and access to the area may be closed in cases of inclement weather. But as soon as Lake Superior’s surface has adequately frozen for safe travel, you’ll be able to explore the ice caves in person! Behold the magnificent icicles and crystalline surfaces of the lake and sandstone cliffsides. It’s a round trip distance of 3 to 6 miles depending how far you choose to walk on the trail. Great for busting winter boredom and cabin fever!

White Pines Ranch; Oregon IL

126 Miles from Classic Car Dealerships

The Ranch is a beautiful 200 acre swathe of land with wooded areas, a sandstone canyon, horse trails and pastures, and places to hike. Bring the kids and enjoy a day of horseback riding, visit with the local animals, and just take in the breathtaking views. Enjoy the peace and quiet solitude of the area when snow blankets the pastures and creates a magical winterscape! You can even enjoy workshops such as wilderness survival, enjoy some cross-country skiing, have a blast sledding, or kick back and relax with some crafting. There’s lots to do at any age! Book a stay and enjoy a late autumn, early winter getaway as an early holiday gift for the whole family.

Depot Pond; Batavia IL

70 Miles from Classic Car Dealerships

If you’re visiting in Autumn you can enjoy a leisurely stroll along the riverwalk which connects Depot Pond and Fox River. It’s got some truly beautiful views of the riverside and shorelines. A classic spot for ice skating and winter activities as soon as the ice measures 8” thick or more! It has even inspired several painters and artists to capture the whimsical winter wonderland and wide-eyed joy of children learning how to skate. Pending on weather and seasonal closures, you might even want to visit the Batavia Historical Society’s Depot Museum nearby.

Starved Rock State Park; Oglesby, IL

123 Miles from Classic Car Dealerships

This state part is beautiful all year round, but visiting during the autumnal Golden Hour or in the early weeks of winter with fresh snowfall are a real treat! Whether you’re hiking or perhaps birding in search of a Bald Eagle and the migratory birds or just taking your camera for a spin in hopes of catching a whitetail deer mid-leap, you’ll find plenty of exciting things to do here. The region includes the St Louis Canyon, French Canyon, and Wildlife Canyon and their beautiful waterfalls. Enjoy views of the Illinois River as well as Starved Rock Dam as you explore these sandstone glacial canyons. A wonderful place to visit during each season to observe the change in the landscape and scenery.

Do you have a favourite place you like to visit in the area?

We’re always interested in hearing from our readers about new places to visit in Wisconsin and Illinois. Let us know your picks and we may just feature your suggestion in a future post!