❄️ Winter Wonders in Wisconsin: Your Ultimate Driftless Region Bucket List

Looking for things to do in Wisconsin in winter that don’t involve hiding under a pile of blankets? Allow us to introduce the Driftless Region—a magical land of bluffs, frozen waterfalls, charming towns, and holiday cheer that refuses to drift into boredom once the snow starts falling.

From cross-country skiing and ice fishing to quirky festivals like the "Droppin’ of the Carp," this guide is your one-stop-shop for winter fun in Wisconsin—and trust us, this bucket list is so good, it’ll make even snow-haters crack a frosty smile.

🏔️ What Is the Driftless Region, Anyway?

Let’s start with the basics. The Driftless Area is a unique geological region in southwest Wisconsin (plus parts of Minnesota, Iowa, and Illinois) that the glaciers skipped during the last Ice Age. That means no flattened land—just bluffs, valleys, caves, and wild beauty, especially when coated in a glimmering layer of snow.

The Wisconsin side of the Driftless Region is home to small towns like La Crosse, Viroqua, Prairie du Chien, Sparta, and Onalaska—each offering its own winter magic.

Now, let’s hit the trails, towns, and toboggans.

🎄 Can’t-Miss Holiday Events in Early December

December kicks off with a sleigh-full of festive fun:

🌟 Rotary Lights at Riverside Park – La Crosse, WI

• Dates: Nov 28 – Dec 31, 2025
  
  
• Over 3 million twinkling lights, a 140-ft animated tree, live Nativity scenes, bonfires, carriage rides, Santa visits, and even ice skating (weather permitting).
  
  
• Walk or drive through this beloved Wisconsin tradition while donating to local food pantries.
  
  

🚂 CP Holiday Train – La Crosse Stop

• Date: Dec 11, 2025
  
  
• A holiday-decorated train pulls in for a free live concert on a boxcar stage, with performances and food drive support. It’s Christmas on rails, and yes—it’s as magical as it sounds.
  
  

🧣 Run, Rock, and Revel with Holiday-Themed Activities

🎽 Ugly Sweater 5K – Dec 6, 2025

• Grab your goofiest holiday sweater and run from Myrick Park to Rotary Lights.
  
  
• Kids under 10 run free with a donation! Expect warm drinks, music, and festive cheer at the finish line.
  
  

🎶 “A Holly Jazzy Christmas” – Dec 11–12

• Big-band jazz meets holiday vibes at the Cappella Performing Arts Center in La Crosse. Cozy up with this toe-tapping concert that’ll have you swinging all the way home.
  
  

🎻 La Crosse Symphony Holiday Glories – Dec 20

• Enjoy soprano vocals and audience sing-alongs at the Viterbo Fine Arts Center—because nothing says “holiday magic” like a symphony of carols under velvet lights.
  
  

🖼️ Culture with a Holiday Twist

🖌 First Friday Downtown Art Walk – Dec 5

Explore La Crosse galleries, artist receptions, and live music while sipping seasonal sips.

🕯 Holidays at Hixon House Tour

Also on Dec 5, step back into a 1940s candlelit Christmas at this mid-century home decked out in period décor.

🎿 Outdoor Adventures Worth Layering Up For

Let’s talk trails. The Driftless Region is a winter playground for nature lovers, with groomed ski trails, frozen waterfalls, and scenic snowshoe paths.

Top Spots for Cross-Country Skiing & Snowshoeing

• Kickapoo Valley Reserve – La Farge
  
  
  
  • 10+ miles of groomed trails
    
    
  • Ice caves, sandstone cliffs, and peaceful forest paths
    
    
  • Rentals available
    
    
• Wildcat Mountain State Park – Ontario
  
  
  
  • Bluff-top views with multiple overlooks
    
    
  • Family-friendly with cozy rest shelters
    
    
• Wyalusing State Park – Bagley
  
  
  
  • Ski through wooded loops overlooking the Mississippi
    
    
  • Snowshoe to frozen waterfalls and caves
    
    
• Governor Dodge State Park – Dodgeville
  
  
  
  • 12+ miles of skiing, snowmobiling, and sledding hills
    
    
  • Fish, slide, or ski—all in one place
    
    
• Blue Mound State Park – Blue Mounds
  
  
  
  • Known for top-tier Nordic ski trails in southern Wisconsin
    
    
• Perrot State Park – Trempealeau
  
  
  
  • Ski along bluffs and eagle-watch at Brady’s Bluff
    
    

🐟 Ice Fishing & Sledding: Chill Thrills Await

If your idea of winter fun includes frozen lakes and flying down hills, you’re in luck.

Ice Fishing Spots

• Lake Onalaska
  
  
  
  • Easy access and big catches (bluegill, perch, crappie, pike)
    
    
  • Nicknamed the “Sunfish Capital of the World”
    
    
• Mississippi River Backwaters
  
  
  
  • Head to Ferryville, De Soto, or Prairie du Chien
    
    
  • Bring a shanty and fish beneath soaring eagles
    
    

Sledding Hills Worth the Climb

• Governor Dodge State Park
  
  
  
  • Classic tobogganing fun near Twin Valley Lake
    
    
• La Riviere Park – Prairie du Chien
  
  
  
  • Chill, kid-friendly sledding with wide-open safety zones
    
    

🦅 Scenic Views & Wildlife Watching

Grandad Bluff – La Crosse

Breathtaking views of the city and Mississippi River. Sunrise or sunset? Either way, it's a win.

Mississippi River Eagle Watching

Top viewing spots:

• St. Feriole Island
  
  
• Lock & Dam #8 (Genoa)
  
  
• Ferryville
  Watch bald eagles dive for fish in one of the best birding areas in the Midwest.
  
  

🛼 Indoor Fun for Chilly Days (Or Just When You Need to Thaw Out)

For Families and Kids

• High Roller Skating Center – La Crosse
  
  
• Jump Start Adventure Park – Trampolines, cosmic jumps, ninja courses
  
  
• Play Grounds of La Crosse – 17,000 sq. ft. of soft play and climbing structures
  
  
• Children’s Museum of La Crosse – 3 floors of hands-on fun including a pretend Kwik Trip (how Wisconsin is that?!)
  
  

For Adults (or the Young at Heart)

• The Great Escape + Driftless Axe – Test your puzzle-solving skills or throw axes like a Viking
  
  
• Pearl Street Brewery Tour – Sip local craft brews in a cozy historic taproom
  
  

⛸️ Ice Skating, Anyone?

• Lake Neshonoc – Outdoor natural rink surrounded by Driftless hills
  
  
• Onalaska Omni Center – Public indoor skating on Sundays
  
  
• Green Island Ice Arena – Indoor rink, no weather worries
  
  

🛍️ Winter Markets & Local Holiday Shopping

Viroqua Public Market

Feels like a European indoor street market with food, crafts, and vintage finds.

Driftless Area Holiday Craft Fairs

Pop-up markets across local towns feature handmade gifts, treats, live music, and—of course—hot cocoa.

🎅 Unique Events & Guided Experiences

Sparta Kriskindlmarkt – Weekends through Dec 21

Like a Hallmark movie come to life.

• Over 40 vendor huts
  
  
• Mulled wine, artisan gifts, fire pits, Santa sightings
  
  
• Carriage rides + live music
  
  

Kickapoo Valley Winter Festival – La Farge

• Horse-drawn rides, sledding, ski demos, and ice cave hikes
  
  
• Free and family-friendly
  
  

Wildcat Mountain Candlelight Hike – Ontario

Lantern-lit trails, bonfires, and cocoa under the stars? Yes, please.

🎇 New Year’s Celebrations, Driftless Style

Grandad Bluff Fireworks – La Crosse

Family-friendly show at 6 PM AND midnight spectacle with citywide views.

Carp Fest & Droppin’ of the Carp – Prairie du Chien

• Dec 29–31
  
  
• Count down to the New Year with a 30-lb frozen carp named Lucky being lowered from a crane
  
  
• Enjoy bonfires, games, ice fishing, fireworks, and music
  
  
• Quirky, charming, unforgettable
  
  

📅 Bonus: Stay Plugged In with the Driftless Club

Want even more winter fun at your fingertips?
Sign up for the Driftless Club to get:

• One quick text every Thursday night with weekend plans
  
  
• One Sunday email to plan your week
  
  
• Exclusive offers from local businesses
  
  
• And zero spam—just vibes

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