With several distinct regions to choose from, Wisconsin is perfect for weekend getaways. The seven itineraries here can either be used as-is for a weekend, or combined in almost any way for longer trips. Door County and the Wisconsin Dells are the most popular getaways in the state.
Save this beer-centric city for a long weekend. After exploring Milwaukee, head to Door County or westward to the capital, Madison.
Driving to Milwaukee from Chicago, choose Kenosha, Racine, or a boat tour of Lake Geneva along the way. A drive through the Kettle Moraine State Forest-Southern Unit is a primer on glacial history right near a walk-through people’s history at Old World Wisconsin. In Milwaukee, stay downtown in the historic Pfister or at Brewhouse Suites, located in the renovated Pabst Brewery just northwest of downtown.
After exploring Madison and Devil’s Lake, you’re so close to the Wisconsin Dells that you should try to combine the trips if you can.
In Madison, start with the architectural gems: Frank Lloyd Wright’s Monona Terrace and, a few steps away, the magnificent State Capitol. Stroll the pedestrian-friendly State Street area to the University of Wisconsin-Madison campus. The University of Wisconsin Arboretum has the best urban trails anywhere, or visit the Olbrich Botanical Gardens. Downtown is the lovely Mansion Hill Inn; alternatively, on the near west side, the ecofriendly Arbor House perfectly fits the ethos of Madison.
Choose a longish drive northeast to the extraordinary Horicon Marsh Wildlife Area or a combination circus experience and workout in Baraboo and Devil’s Lake State Park. During the spring or fall migratory periods, visit Horicon Marsh; otherwise, Devil’s Lake is a gem of a park.
3. Door County
Door County is easily reached from Milwaukee and Madison. It’s also customary for Wisconsin football fans to pilgrimage to Green Bay and Lambeau Field on the way to Door County or on the way back. You could substitute one of the days in Door County with a ferry ride to quiet, great for biking Washington Island and potentially another short ferry ride to Rock Island State Park to hike as far as you can get from the mainland.
First day—explore the bay side of the Door’s sublime natural environment and grand food, lodging, and shopping. Must-sees for nature and recreation are Potawatomi, Peninsula, and Newport State Parks. Spend the night in Fish Creek for the food and shopping; top picks for lodging are the White Gull Inn or the Whistling Swan.
On your second day, explore the lakeside. Must-sees are hiking or kayaking at Whitefish Dunes State Park or The Ridges Sanctuary as well as the nation’s densest county concentration of lighthouses. This is the more tranquil side of Door County, and some people spend their entire weekends on this side for that reason.
4. Wisconsin Dells
Following a riotous trip to the Dells, you could head southwest to explore the rivers of Wisconsin.
Pick a megaresort and let the water-slide fun commence. Make sure you do your homework; you can get some amazing deals. Top choice for a place with capital-E everything is the amazing Kalahari Resort Convention Center for indoor and outdoor waterparks, rooms, villas, and many other options.
See the real Dells of the Wisconsin River on the World War II-era duck boat tour. If you’ve had your fill of water, Devil’s Lake State Park down the road offers superb hiking and, next door, fetching Baraboo is small-town quaint and has a grand circus museum, replete with outdoor shows.
5. The Northern Cap
From the Northern Cap, the Great North Woods are nearby.
Drive to Bayfield on a Friday and eat whitefish. Stay at the budget Seagull Bay Motel, or for a splurge, the Old Rittenhouse Inn cannot be beat for the historic lodgings and epicurean delights.
In the early morning either kayak the sea caves or cycle the rolling hills filled with apple orchards, then in the afternoon either take a shuttle to an island and hike or take the grand evening boat tour of the Apostle Islands National Lakeshore for amazing vistas.
Spend today driving the extraordinary Highway 13 along Lake Superior to Superior to see the big lakers (freight ships) and waterfalls.
6. Great North Woods
Combine the Northern Cap and the Great North Woods for a week of outdoor bliss.
Get a cabin, cottage, or resort room in Hayward in northwest Wisconsin, or in the northeast, in the Minocqua area, Eagle River, or Boulder Junction. Spend the day with a rowboat, canoe on the lake, or nap to the sound of lapping water.
From Hayward, spend a day at the National Freshwater Fishing Hall of Fame and a lumberjack show. From Minocqua, visit Waswagoning or the Turtle-Flambeau Flowage. If you’re in Eagle River, spend your second day on a snowmobile in winter or fishing the amazing Eagle River Chain of Lakes.
7. Southwestern Wisconsin
From the Great North Woods, head south. Southwestern Wisconsin is also close to the Dells.
Camp at Wildcat Mountain State Park or stay at the extraordinary Inn Serendipity Woods; either canoe the extraordinary serpentine Kickapoo River or bike the original U.S. rail-to-trail path, the Elroy-Sparta State Recreational Trail.
Drive very slowly in the region, the Coulee Range, to wave at horse-drawn buggies of the Amish, and visit one of their amazing bakeries for great sustenance. The Amish should only be photographed with permission.
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