12 Best Towns In Wisconsin For A Winter Getaway
Winters in the north can get rough, but the sun keeps shining down the mountains, reflecting in the lakes, and off the historic architecture in the best towns for a cold-weather getaway in the Badger State! Why settle for the traditional cheese curds and beer at your local pub when you can aspire to a Eurotrip through Germantown, Stockholm, and two Norwegian towns? In the lesser-known town of Princeton, you can feel like visiting royalty on a wine and cheese retreat. Go to Wisconsin Dells for waterparks or enjoy spas in Swiss-inspired elegant Lake Geneva, and there is no better way to defy a cold winter evening than a performance at the Phipps Center for the Arts in Hudson. Elkhart Lake and Land O'Lakes are popular towns for outdoor activities.
Bayfield
As the "portal" to the 22 Apostle Islands, Bayfield is an endlessly giving getaway destination, with a lot to discover along its own shores of Lake Superior before setting seabound! Dressing up in every season, the small town and coastal nature, like the frozen beaches of none other than the Apostle Islands National Lakeshore, are spellbinding! You can enjoy lakeside strolls along the 12-mile forest fringe or deeper ventures like snowshoeing, skiing, or fat-tire biking through the dramatic landscape! Don't expect low crowds, but a ferry ride to Madeline Island, the most popular among other islands, delivers the spectacular remote scenery.
With so much outdoor recreation, there's matching demand, but also great entertainment and relaxation opportunities. Thanks to favorable geography and an ideal growing environment for fruits and berries, literally nothing is off the table in Bayfield, where you can enjoy delectable strawberries, blueberries, and cherry pies off-season through cafes with your hot cocoa cup! This quaint fishing village of immaculate beauty is full of galleries and wineries, as well as gorgeous old buildings with fireplaces to relax against the lake views! From farm-to-table dining to whimsical lodging, you can stay at our favorites, Old Rittenhouse Inn and Queen's View!
Elkhart Lake
Elkhart Lake, a resort town in the middle of Kettle Moraine State Forest, attracts summertime crowds with a clear lake at the center, staying peaceful through winter for R&R against the frozen shores! With a great park system and waterside trails, you can spend an afternoon at the family-friendly Fireman's Park and Beach, the paved paths through Jeanette Moioffer Park and June Vollrath Park, or hop on a boat tour for the town's lights from another side! The holiday charm stays long after in the lake village downtown, with its adorable shopping aplenty and cozy cafes for some warming hot cocoa!
Home to mindful locals, Elkhart Lake is all about health and wellness, which feels particularly indulging in the cold weather at the pampering Aspira Spa after a morning run or bike ride on the Four Miles of Fitness trail. Generous in its wining and dining options, you can unwind over local farm-to-table cuisine and wind down in elegance at the historic Osthoff Resort from 1885. Its sprawling waterfront property with panoramic suites, perfect for couples and families, feels like an old-timey holiday that you can introduce your kids to, as well as its own Christmas Market!
Germantown
Wisconsin Territory's "Town Nine" in 1836, Germantown, was the oldest settlement in Washington County, with German and Irish immigrants followed by Yankee migrants. Largely agricultural at first, it is easy to see how the cultural blend expanded the economy, and the deep German brewing heritage became prominent. Just 30 miles northwest of Milwaukee, Germantown residents are a welcoming bunch you can meet at Vogel, Regenfuss, and Staats breweries from the late nineteenth and early twentieth centuries. There's also a picturesque basilica nearby that looks more like a majestic castle, with miles of rolling hills around it covered in snow.
This winter, you can experience European vibes at the authentic, magical outdoor beer garden at Von Rothenburg Bier Stube, pouring dozens of German beers from tap over classic specialties like giant hot pretzels and Schnitzel. Imagine its celebration of the annual local Oktoberfest, or better yet, return in September for live music, dancing, and fun for the whole family like Dachshund Dash! Just 10 miles away from the cozy town, Holy Hill National Shrine of Mary, on a glacial hill, stuns with its neo-Romanesque architecture. With many lodgings along the highway, you can stay at the top-rated Home2 Suites by Hilton Menomonee Falls Milwaukee or the reliable, budget-friendly Super 8.
Hayward
This small town will get you through the coldest days with its warmest heart and hot-headed locals who enjoy four-season outdoor recreation opportunities here in Wisconsin's Northwoods. Home to its own sizable Hayward Lakes, minutes stroll from downtown, there are many waterside lodgings like Riverside Motel and Holiday Inn Express & Suites Hayward. Just fifteen minutes north, you can try ice fishing in Round Lake or Nelson Lake for perch and walleye or rent a fat tire bike or cross-country ski along the world-class trails groomed for the American Birkebeiner Ski Race when it is not underway.
Dial it up and expand your horizons on a rented snowmobile rummaging through the surrounding country and woodlands, with hundreds of miles connecting to other small towns! You can explore the many lakes in their wintertime state, including the Chippewa Flowage, 30 minutes south, and return in the summer for watersports and muskies in this third-largest lake in the state. Home to rental shops as well as many small, family-owned restaurants, Hayward is the perfect town to ring in the new year with those who matter!
Hudson
Hudson, just outside of the Twin Cities, is the perfect place to spend a winter weekend, with festive holiday lights through mid-February, a great park system, and ski trails on the other side of the river. Bundle up and explore nature, or grab some hot cocoa in between local shopping or skating on the beautiful Perch Lake. Just outside, the enchanting Eagle Eye Farm welcomes you to share the joy with happy farm animals, including their award-winning alpacas, llamas, and miniature highland cattle. There's no better way to defy a cold winter evening than a performance at the Phipps Center for the Arts featuring art, dance, and theater productions as well as rotating exhibits.
One of the most notable landmarks, The Real Magic House, is the oldest home in the area, dating from 1885, with extensive history, detail, and character to discover on a tour! Guess what? You can also stay at this premier vacation rental and unwind at nearby award-winning restaurants and year-round patios! Pier Five Hundred features igloo-style dining, while Pedro's del Este offers Spanish, Cuban, and Latin flavors in a warm, see-through pergola. Try and find a better reason to visit than the Midwest's largest balloon festival right here, Hot Air Affair, February 2-4, or come now for plays and concerts, shopping, or the Willow River State Park's miles of hard-packed trails for snowshoeing and dog sledding.
Lake Geneva
From Christmas market treats to winter festivals, resplendent shopping, and petting zoos, for the love of boutiques and cafes, visit Lake Geneva—your classic small lakeside town retreat! The family-friendly town, most popular among Chicago day trippers and adventurous souls, will meet and exceed your wintertime escape to relax from the chaos of work and life. The deserted beach is still a top pastime, while the Grand Geneva Resort and Spa will take care of your soaking needs with full-service and unmatched lake vibes, in addition to horseback riding! You can zipline over the forest with Lake Geneva Zipline Tours or kick back and soak up the immense Lake Geneva scenery on a boat tour.
With an old-world resort elegance and stunning lake scenery for morning strolls, the real estate envy along the shores can be your own luxury waterfront stay. There's the spectacular walking Lake Geneva Shore Path from Elm Park to Lake Geneva Public Beach, with the most popular eateries of the Oakfire and Egg Harbor Cafe nearby! You can glimpse at how the famous Broadway notables Alfred Lunt and Lynn Fontanne decorated and lived in their home on a tour of Ten Chimneys Estate and feel like the affluent vacationers in the late 1800s at the luxurious Black Point Estate and Gardens. Lake Geneva Lodge and Bella Vista Suites are budget- and family-friendly options, perfect for couples!
Land O'Lakes
This small town, like a Norman Rockwell card setting, is one of the coziest spots during the winter in Wisconsin. With its name in over 100 beautiful lakes, Lake O'Lakes is a real angler's paradise, like outstanding fishing at the 15 interconnected Cisco Chain of Lakes and crystal-clear Lac Vieux Desert for world-record tiger musky. From Heritage Park for strolls to 12 miles of trails—some of the best hiking and biking trails in the Northwoods—the nearby woodlands and Sylvania Wilderness offer up primitive camping sites, birdwatching, and mountain biking.
Whether you are in for the lakes or the trails, winter wonderland scenery prevails here in Vilas County. You can bundle up for some ice fishing under the winter sun in the peaceful serenity of the crisp, picture-perfect trees covered in snow and warm up with plentiful, delicious food stops, restaurants, sweet treats, and gifts to browse with your loved ones through quaint shops! The most popular Caliente Club & Resorts aspires to the tropics with greens and a pool, while the megapopular Flying Squirrel Trampoline Park in the south of town is an unforgettable winter day activity for the kids.
Princeton
This small, family-friendly city in Western Green Lake County of roughly 1200 outdoor enthusiasts with a taste for diverse ideas enjoys abundant natural resources on the Fox River. Flowing right through the city with historic buildings to one side, you can enjoy fishing, hunting, canoeing, golfing, cycling, and camping, all readily available throughout the year. With cute restaurants, bakeries for fresh-baked breads and pastries, wine, and more cheese than you can imagine, Princeton is a delightful winter getaway in central Wisconsin!
Princeton boasts a quaint downtown with imposing traditional architecture and a delightful mix of specialty shops, including boutiques and artisans, perfect for holiday shopping. From books to local pottery and other crafts like candles and jewelry, stick around for sales through clothing boutiques and great antiquing! You can stay at the nearby Acorn Ridge Motel between the town and Green Lake, just 10 minutes south, with access to Dodge Memorial County Park, and return for "Wisconsin's Largest Weekly Outdoor Flea Market," seeing upwards of 70,000 annual visitors from May to October.
Stockholm
With a persistent population of 76, this truly small town along the Mississippi River, across from Minnesota, just off the Great River Road, is a mecca for culture and traditional festivals. The charming village has craftily weaved heritage into the natural beauty of the Driftless Region since its founding in the mid-1800s by Scandinavians amid picturesque countryside on their westward travels through Wisconsin. Stockholm pulls you in with family-friendly attractions, waterfront stays, and riverside strolls to where it meets Lake Pepin, with beautiful bluffs you can relax under or hike over! The genuine Scandinavian décor makes for one-of-a-kind gifts, while Scandihoo is full of hygge vibes with sustainable fashions, and perhaps after the holiday sales!
With Swedish-influenced art through galleries, boutique shops with local craftsmanship, and highlights like Adobe Gallery and Ingebretsen's, Fresh Art Tour offers a spin through the neighboring artistic enclaves of Pierce and Pepin. Stay busy outside and warm up inside at small eateries and cafés over authentic delicacies like Stockholm Pie & General Store, for their made-from-scratch pie or the savory Smoked Salmon Smorgas. You can unwind at Maiden Rock Winery & Cidery, with views over tastings featuring European-style ciders and wines, and wind down at Maiden Rock Inn, in a beautiful historical building just north along the shore.
Stoughton
With a storied past and bursting cultural flavor, Stoughton, just southeast of Madison, saves you money and the hassle of traveling to Norway with all the authentic, historic, and fun attractions in this charming town. The picturesque main street takes it up a notch for the holidays through one-of-a-kind small businesses like Nordic Nook for traditional and high-quality Scandinavian gifts and apparel. Lang Lighting and Decor is adorned in Christmas for unique homeware, decor, and browsing pleasures, while Livsreise—"Life's Journey"—is Stoughton's Norwegian Heritage Center, with interactive and story-telling exhibits of emigrants from the 20th century.
With the Yahara River through town and waterfront greens like Bjorn Park, Viking County Park features a dog park, while Lake Kegonsa State Park is your ultimate outdoor escape. The must-visit Viking Brew Pub in a wooden Viking ship combines American and Scandinavian cuisines with everything from traditional Norwegian meatballs to house-made potato chips in a Valhalla dip to Wisconsin cheese curds, paired with 12 brews on tap! You can feed adorable baby goats from a milk bottle at Eugster's Farm Market, stay at big-name hotels for under $100, including Hilton, and return for the Syttende Mai Folk Festival in May with music, dancing, and a parade!
Westby
Guess what? You are still in Norway, but with another set of attractions in this cute town, settled in the 1840s by Norwegian immigrants. Part of the Driftless area, the rugged countryside remains a popular escape for a scenically charged getaway under the winter sun along the Elroy-Sparta Trail and through Wildcat Mountain State Park. Just southeast of La Crosse, Westby is your getaway to the Kickapoo Valley Reserve, while Snowflake Ski and Golf Club and Nordic Bowling Lanes are great ways to stay active away from the cold! From nearby vineyards to the awesome Norskedalen area with restaurants and a farm to warm up, don't miss the photo opportunity with "Ole," the city's wood-carved mascot, at the "Stabur," the tourism information.
You can start at the must-visit Ole and Lena Kaffe Hus, with plenty of down-home cooking cafes and supper clubs in between, and Westby Co-op Creamery to taste local cheeses, yogurt, and butter. The annual Westby's Snowflake Ski Jumping Tournament, February 2–3, is as good a reason as any to join a large international crowd for this North America's premier ski jumping event, with global competitors! From historic inns to quaint cottages, there's no shortage of memorable stays, but the Old Towne Motel is an easy-budget favorite. Come anytime for family fun in the lively downtown with historic architecture, cultural attractions, and shopping like Dregne's Scandinavian Gifts, while the annual Syttende Mai is a mid-May celebration of Norway's Constitution Day with traditional entertainment, including a parade!
Wisconsin Dells
Home to indoor waterparks, Wisconsin Dells, a small town of over 4,000, is a resplendent place for a winter getaway in the state! With a family-friendly feel, spas and stays combined, and gorgeous scenery, you can shake off your winter blues and warm up over great food, shopping, and visiting wineries! At the heart of town, the Atlantis Family Waterpark Hotel, one of the best kid-friendly resorts in Wisconsin, is a fantastic choice to splurge on a getaway. With plenty to see and do on site within a vibrant and playful decor, you can enjoy its spacious rooms and a designed waterpark with crafted waterslides and cozy cabanas to relax and have fun!
The town truly has it all, including nearby skiing, snowmobiling, and some of the best snowboarding, which you can get free passes to when you stay at Mt. Olympus Resort. It offers a wide range of amenities, like a great après-ski scene and nearby attractions like the Tommy Bartlett Show! Wisconsin Dells makes for an unforgettable escape to celebrate the holidays or relax after, with breweries, wineries, and distilleries, as well as museums and exhibits like Timbavati Wildlife Park. The Wisconsin River runs right through town, while Lake Delton is just south of downtown for all your shoreside strolls between waterfront spas.
Wisconsin inspires outdoorsy, luxury seekers, and entertainment gumbos. From the Northwoods to the Driftless Area, there are more lakes than you can fit in a year, let alone a getaway, all in only a medium-sized state—the 23 largest by area and the 20 most populous. Winters and Wisconsin just go together! With operating boat tours and zip lines zooming, you can take the Fresh Art Tour for a spin through coastal artistic enclaves from Stockholm, amounting in culture, while Bayfield is your "portal" to the 22 Apostle Islands.
