Winter Adventures: Skiing, Snowboarding, and Cozy Cabins in Wisconsin
Just about 30 miles northwest of Milwaukee lies Holy Hill, officially called the Basilica of the National Shrine of Mary, Help of Christians. While it’s famous for its soaring steeple visible for miles, this hilltop also serves as a surprisingly scenic winter destination, especially when snow blankets the rolling Kettle Moraine landscape. Visitors can explore the surrounding trails, such as the Short Loop or Long Loop, which offer peaceful woodland hikes perfect for snowshoeing or cross-country skiing. The unique mix of ancient glacial formations and frost-covered evergreens creates a serene atmosphere that’s both spiritually uplifting and naturally beautiful. Winter mornings here, especially when the low sun filters through frosty branches, give way to quiet moments that feel a world away from the city—ideal for those wanting to combine outdoor activity with a touch of reflection and history.
Further north, in the Driftless Area near La Crosse, about two hours northwest of Madison, the ski slopes of Mount La Crosse provide a lively playground for winter sports enthusiasts. This ski hill features a variety of runs catering to beginners and intermediates, with a few challenging black diamonds for more experienced skiers and snowboarders. What makes Mount La Crosse stand out is its intimate, family-friendly environment combined with panoramic views overlooking the Mississippi River valley. The elevation and natural terrain create a satisfying descent over well-groomed trails, and the lodge offers cozy spots to warm up with hot chocolate after a day on the slopes. The best time to visit is when fresh snow has recently fallen, turning the hill into a crisp, white canvas perfect for carving turns and practicing jumps.
In northern Wisconsin, just a short drive east of Rhinelander, the Granite Peak Ski Area ranks among the state’s premier winter resorts. Sitting in the scenic Nicolet National Forest roughly four hours north of Milwaukee, Granite Peak boasts one of the highest vertical drops in the Midwest and an impressive variety of runs—spanning over 70 skiable acres. Its extensive trail system includes long cruisers, steep pitches, and terrain parks, making it a magnet for skiers and snowboarders seeking variety and challenge. The surrounding pine forest dusted with snow creates a picture-perfect alpine setting unlike many other Midwestern hills. Winter visitors will appreciate the modern lift system that minimizes wait times and the rustic yet comfortable base lodges where one can unwind by the fire. Granite Peak’s winter season can stretch from late November into early April, depending on snowfall, providing ample opportunity to enjoy powder days in a natural northern lakeside environment.
For those who prefer a different kind of winter getaway, the town of Bayfield, located on the shores of Lake Superior about three hours north of Duluth, Minnesota, offers a cozy cabin retreat combined with unique snowshoeing and cross-country skiing on Apostle Islands National Lakeshore trails. This area’s rugged shoreline and dense forests transform under snow, inviting visitors to explore quiet paths like the Stockton Island Loop or Meyers Beach Trail. These trails wind through hardwood forests and along icy cliffs, often offering glimpses of frozen waterfalls and abundant winter wildlife such as bald eagles or deer. Bayfield’s charming downtown, with its historic architecture and welcoming inns, adds a warmth and hospitality that balance the winter chill. The best months to visit are January and February when snowfall is plentiful but the lake’s icy presence keeps the landscape dramatic and still.
In the western part of the state, just over an hour northeast of Eau Claire, Blue Hills Trail System in the Chequamegon-Nicolet National Forest provides a vast network of groomed cross-country ski trails and snowshoe paths. This area is treasured for its extensive, well-maintained routes that range from easy loops to more rigorous climbs, passing through mature hardwoods and pines blanketed in snow. Blue Hills is distinguished by its expansive terrain and the quiet solitude it offers, far from crowds. Winter visitors can glide through peaceful woods with occasional open views of frozen lakes and marshes, making it both a nature lover’s haven and a fitness challenge. Early morning and late afternoon visits are magical here, as soft winter sunlight filters through bare branches, casting long shadows on the snow.
Near the charming city of Wausau, about two and a half hours north of Madison, Granite Peak’s neighbor, Sylvan Hill Park, offers a smaller-scale but beloved ski and sledding hill nestled within town limits. This hill is perfect for families and those new to snow sports, with gentle slopes, beginner-friendly terrain, and a welcoming community vibe. Sylvan Hill also features a terrain park where snowboarders and freestyle skiers can practice tricks and jumps. The night skiing options add an extra layer of excitement, allowing locals and visitors alike to enjoy crisp winter evenings under floodlights. Its accessibility and friendly atmosphere set it apart from larger resorts, making it an excellent stop for those seeking a more relaxed pace without sacrificing winter fun.
For a truly cozy winter experience, the town of Minocqua, nestled amid the Northwoods about three and a half hours north of Milwaukee, invites visitors to stay in rustic cabins surrounded by snow-covered forests and frozen lakes. This region is renowned for its quiet beauty and classic winter charm, where guests can enjoy peaceful mornings watching wildlife tracks in fresh snow before heading out on the nearby Bearskin State Trail. This multi-use trail offers miles of groomed paths for cross-country skiing and snowmobiling, winding through dense woods and open fields. Minocqua’s cabins, many with stone fireplaces and wooden interiors, provide the perfect retreat after a day outdoors, enveloping visitors in warmth and the scent of pine. Winter here is at its best from December through February, when long nights and snowy days encourage slow, restorative vacations centered around nature.
Just south of the Wisconsin Dells, Cascade Mountain Ski Area rises above the rolling countryside about an hour west of Madison. Known for its well-maintained slopes and friendly staff, Cascade Mountain offers a mix of beginner, intermediate, and advanced runs that cater to families and avid skiers alike. The hill’s elevation and snowmaking capabilities ensure reliable conditions throughout the season. Unique to Cascade are its frequent ski competitions and events that bring energy and camaraderie to the hill. Visitors can enjoy a scenic chairlift ride that provides sweeping views of the Wisconsin River valley—a breathtaking sight when framed by frost and snow. Afternoons here, when the sun softens the snow on south-facing slopes, are perfect for leisurely rides and lingering at the hilltop lodge for a warm beverage.
Each of these destinations encapsulates a different facet of Wisconsin’s winter spirit—from challenging downhill runs and expansive cross-country trails to tranquil snowshoe paths and snug cabins. Together, they weave a tapestry of snowy adventure and cozy comfort, inviting travelers from all over the country to experience the Midwest’s white wonderland on their own terms.