When you think of Wisconsin, darling Main Streets with town parks or squares and cute shops might come to mind. Outside of metropolises like Milwaukee, Green Bay, the Fox Cities, and Madison, these picture-perfect villages are in abundance. And no matter the season, whether autumn’s leaves are whirling or snowflakes spinning, a day trip is an ideal city break. Need more time to explore? An adorable inn may be calling your name.
Ninety minutes north of Milwaukee lies this vintage-y town. Rent a stand-up paddleboard to cruise around the namesake lake, hike a portion of the Ice Age Trail (LaBudde Creek segment), or dial it down with a treatment at The Osthoff Resort’s Aspira Spa. Two long-time eateries dish up cuisine rivaling that of the big cities: Paddock Club and Lake Street Cafe. Duck into Nordic Accents for homeware imported from Norwegian countries or, at Vintage Elkhart Lake, Wisconsin artisan cheese, wine from around the globe, or sommelier-owner Jaclyn Stuart’s private-label line of gourmet foods for an impromptu picnic.
Where to Stay: The Shore Club Wisconsin’s new owners crafted a beach-house vibe in each of the guest rooms, plus a Tiki bar and quirky touches like a life-sized chess set on the lawn.
On the quiet side of Door County, a peninsula wedged between Lake Michigan and Green Bay, this small town boasts a fine-dining restaurant (Chives) and hiking at The Ridges Sanctuary. Walk the Lake Michigan shoreline, including a pier jutting out into the water, by day and come evening, sip craft beer at Door County Brewing Co.’s tap room, where live music is sometimes on the schedule. Food trucks are parked in the outdoor beer garden.
Where to Stay: Some Beachfront Inn rooms flaunt wall-sized windows with lake views and you can cozy up to the fire pits along the beach.
Summer is when this artsy town gets the most visitors, thanks to the American Players Theatre’s outdoor shows (a mix of Shakespeare and comedies) and tours of Taliesin, Frank Lloyd Wright’s summer home. At Spring Green General Store, you can sit down to a yummy vegetarian, farm-to-table meal on the covered porch and even pick up holiday gifts in the attached shop. Arcadia Books is another must-do. Love cheese? Pop into Carr Valley Cheese’s outlet store in nearby Mazomanie. And for some quirk, the House on the Rock is a tourist attraction that will marvel you, due to the architecture and kitsch in each room.
Where to Stay: The House on the Rock Resort, not to be confused with The House on the Rock Inn, is the area’s poshest hotel, with a spa, indoor and outdoor pools, dining, a 27-hole golf course, and lots of outdoor recreation.
Anchored by Wisconsin Foodie host Luke Zahm’s Driftless Café, other musts in this town include Driftless Books & Music and visiting local farms, like Wehling Farms, which offers free tours to see the animals on Friday, Saturday, and Sunday as well as a country store you can shop in. (This region ranks among the country’s highest concentration of organic and sustainable farms of a boutique scale.) Another fun stop is at Nordic Creamery’s shop—its butters and cheeses have won international awards and the operation is on its fourth generation.
Where to Stay: Check into the three-suite Tobacco Warehouse Inn, in nearby Soldiers Grove, for apartment-style, stylish accommodations in a building dating back to 1923 and recently restored.
Everybody knows Lake Geneva as an affluent resort town that attracted wealthy Chicagoans during the early 1900s—and is a popular vacation destination today—but fewer people have been to Fontana, on the lake’s other side. Take a short drive to Boxed and Burlap, a cute coffeehouse sharing space with a garden center and event space. If it’s a warmer month, book a short, narrated boat cruise with Lake Geneva Cruise Line, sharing tales about the original occupants of the lake’s opulent mansions more than a century ago. In winter, the lake opens up to ice fishing, another fun activity.
Where to Stay: For the full-service experience, with a spa and on-site dining, as well as amazing lake views from your room, The Abbey Resort delivers.
As the gateway town to the Apostle Islands National Lakeshore, Bayfield itself has a lot to offer, with fruit orchards and farm stands in the countryside, and in town, cafes like Wonderstate Coffee, the beans sourced from its solar-powered roastery in Viroqua. Brush up on local history at the Bayfield Maritime Museum and, if your time allows, visit Madeline Island. As one of the Apostle Islands, it’s the only one inhabited and the former spiritual retreat for the Lake Superior Chippewa.
Where to Stay: You literally can’t miss a glimpse of Old Rittenhouse Inn, a bric-red towering Victorian perched on a hill near downtown. All rooms include breakfast in the dining room, paired with Lake Superior Views.
In the downtown of this artsy community 50 miles southwest of Madison are eclectic shops and art galleries. Local (but nationally award-winning) cheesemaker Hook’s Cheese is known for its exquisite wedges like 15- and 20-year aged cheddar. Drop by its shop on weekdays. Shake Rag Alley Center for the Arts hosts multi-day courses in everything from blacksmithing to paper arts. Two historic museums are in the town: Mineral Point Railroad Depot Museum and Pendarvis Historic Site.
Where to Stay: After a pint at the brewery downstairs, you need only stroll upstairs to one of Commerce Street Brewery & Hotel’s five guest rooms.
You’ll swear you’ve just been air-dropped into Switzerland and that feeling only deepens once you stroll New Glarus’s downtown and order Swiss pastries at New Glarus Bakery, such as nut horns, orange-blossom rolls, and éclairs. Or glimpse the village’s Old World signage. Those in neighboring states flock here to this village snug in Green County, settled by mostly Swiss immigrants, to tour New Glarus Brewing Co.—despite its popularity, the beer’s only available in Wisconsin. There’s also a gift shop.
Where to Stay: New Glarus Hotel, where the restaurant serves fondue.
A rare four-season town when it comes to outdoor adventure—seriously, you can paddle or fish in summer and cross-country ski or snowshoe in winter at Minocqua Winter Park—Minocqua also boasts cute shops in its downtown (from The Shade Tree, a bookstore, to Kilwins for chocolates and caramel apples) and a craft brewery (Minocqua Brewing Company) that’s a buzzy scene at night with live music on occasion.
Where to Stay: Sidestep the town’s chain hotels and rental cottages and cabins for a resort experience The Beacons of Minocqua.