From Ice Roads to Yurts: Bayfield’s Winter Adventures

Throughout millennia, the place we know as the Apostle Islands has left an indelible, almost mythical impression on everyone who’s been there. From lifelong residents with generational ties to casual first-timers—the Bayfield area inspires a profound sense of awe through every season.  

Its first residents, the Ojibwe people, developed a sophisticated and reverent relationship with the lake and land, honoring its bounty and beauty. To this day, Madeline Island, known as Mooningwanekaaning remains the spiritual center for many Indigenous people of the region. The archipelago also left a lasting mark on Wisconsin’s treasured conservationist, Governor Gaylord Nelson, known internationally as the father of Earth Day. His connection and advocacy led to the creation of Apostle Islands National Lakeshore in 1970, the same inaugural year as Earth Day. To say this region is special is an understatement; it is timeless and transcendent.  

In the winter months, this already magical place takes on an even more enchanting aura. Below are some winter adventures in Bayfield that are sure to etch an unforgettable impression on you this season. 

The Frozen Lake Effect 

Lake Superior’s vastness becomes mesmerizing when shaped by ice and wind. Even a short hike in Red Cliff’s Frog Bay Tribal National Park inspires a deeper connection with the big lake. Celebrated as the first Tribal National Park in the country, its trails wind through conifers and hardwoods before leading to a quiet shoreline. Chances are, you’ll have the place to yourselves—linger by the water to catch up or simply soak in the serenity. Even the sight of ice swirling around the distant islands feels effortlessly meditative. 

Back in Bayfield, the Brownstone Trail is a local icon. Start your morning with coffee and pastries from Wonderstate Coffee, a charming downtown spot, then head to the trailhead at the end of 3rd Street near the marina. Renowned for its stunning cliffs, this trail offers a perfect alternative if the conditions aren’t optimal for hiking the Apostle Islands ice caves. Reflect on the magnificence, or, if the mood strikes, start a snowball fight—the backdrop will be glorious either way. 

An Arctic Blast on the Gem of the Apostle Islands 

Expand your horizons on the shores of Madeline Island, the crown jewel of the Apostle Islands. Famous for its island charm and artistic spirit, its backcountry becomes far more exquisite under a blanket of snow. Getting there is half the adventure; the ferry runs as long as the lake hasn’t frozen. But when the lake ices up, the odyssey takes a unique turn, the Madeline Island ice road opens. Surely,  your kids will never forget taking the family car on an ice road to the winter hamlet La Pointe. And if conditions are somewhere in between, the ever-resourceful islanders have a custom-made Windsled; a fascinating snowmobile-hovercraft hybrid.  More than just a novelty for visitors, the Windsled ensures that island’s children and students can always make it to class in Bayfield, no matter the weather. 

Getting to Madeline Island takes a mix of whimsy and determination—keep that spirit alive with backcountry exploration. Big Bay State Park is known for its sandstone cliffs and serene North Woods—landscapes that become even more intricate under snow and ice. The tranquil cross-country ski trails make it easy to connect with both nature and each other. Not a skier? Stroll the boardwalk trail with good traction. 

Splurge-Worthy Winter Escapades 

Bayfield offers every winter pastime, from snowmobiling on 600 miles of trails to skiing at Mt. Ashwabay, with stunning views of Lake Superior. But there’s two bucket-list adventures that uniquely capture the spirit of the region.  

Dog sledding, or mushing, thrives in the snowy interior of the Bayfield Peninsula. At Wolfsong Adventures, you won’t just ride—you’ll learn to drive your own team in half a day. Delve into the backcountry and discover a newfound respect for man’s best friend. And though their huskies are hardworking, they’ll flash their warmest smiles—perfect for the ultimate family photo. 

Like mushing, ice fishing is steeped in tradition. When conditions are right, it is as simple as walking out with basic gear—Chequamegon Bay is renowned for its dependable fishing. Beyond the Catch elevates this classic pastime with guided tours aboard SHERPs, amphibious tanks that access the best fishing spots in any condition. No experience needed—it’s the ultimate mix of classic and high-tech, perfect for an unforgettable bachelor or bachelorette party. 

Winter Respites: From Glam to Yurt Life  

Bayfield may have a summer high season, but there’s no “off-season” when it comes to lodging. Match your mood to the perfect place. 

For a rowdy reunion, opt for the Bayfield Yurts, nestled deep in the woods with stunning lake views. Bring a bottle to toast and spend the evening immersed in board games—who needs WiFi or screens?  For a couples’ getaway, Queen’s View Bed and Breakfast blends Victorian grandeur and Midwestern hospitality, complete with a sauna to melt away winter blues. Prefer a rustic cottage vibe with a touch of luxury? Woodside Cottages of Bayfield offers simple elegance paired with a jacuzzi—the kind of cabin you secretly hope to get snowed in at.