To the untrained eye, the topographical drama of southwestern Wisconsin can feel out of step with the rest of the Midwest. Steep ridges, bucolic hills and rivers that twist around limestone bluffs.
This is the Driftless: a 7,000-square-mile patch left untouched by the last Ice Age. While glaciers flattened much of the region, this particular corner has held its shape. The result is a rolling landscape that looks more like Appalachia than American heartland.
The second leg of WBEZ and the Chicago Sun-Times’ summer art road trip series (find our first trip to Milwaukee here) follows the land the ice forgot, where lakefront crowds give way to creative corners shaped by the terrain.
Madison: A capital city where art and history converge
Tucked between lakes and low-slung hills, Madison blends university energy with a steady rhythm of visual and performing arts. Downtown, the Madison Museum of Contemporary Art hosts the Wisconsin Triennial through Sept. 14, a survey of 24 artists from across the state.
Among the standout works, according to museum director Paul Baker Prindle, are Ho-Chunk artist Tom Jones’s large-scale beaded portrait of a veteran named Levi Black Deer; Teresa Abel’s multi-panel paintings that echo the structure and symbolism of medieval Italian altarpieces; and a winter scene painted by John Riepenhoff. “John Riepenhoff’s paintings are spectacular,” Baker Prindle said. “The one we have is an impressionistic take on the feeling of a night sky. The work is all about atmosphere.”
Architecture lovers should tour the Frank Lloyd Wright–designed Unitarian Meeting House on Madison’s west side. Built in 1951 and still an active congregation, the church is one of Wright’s rare public commissions — and among his most accessible. “It’s a public building that still carries Wright’s full design intent,” said Baker Prindle.
Inside, plywood-and-chain pews speak to his democratic approach to design, while the angular louvered windows cast shifting light across the sanctuary. Unlike the Monona Terrace downtown, which Baker Prindle noted strays from Wright’s original plans, the Meeting House remains largely intact, geometric and grounded.
On the north side of town, Tandem Press — a celebrated printmaking studio affiliated with the University of Wisconsin — offers a more tactile encounter. The studio has collaborated with artists such as Dyani White Hawk, Derrick Adams, Judy Pfaff and Mickalene Thomas, and visitors are welcome to browse and buy prints on-site, many priced under $1,000.
“There’s this very generative sense of collaboration and community,” said director Katie Geha. “Artists leave with a print and often eight new ideas.” For those interested in supporting regional artists, Tandem carries several works by painter and School of the Art Institute of Chicago professor Michelle Grabner, ranging from $500 to $1,800. The studio is open Wednesday through Friday, with printers often at work and rotating exhibitions on view.
After a morning of art, head to Sardine, where fresh oysters and grilled, well, sardines pair perfectly with a view of Lake Monona. For something quicker, Wonderstate Coffee is a reliable stop, especially if the double chocolate cookies (which Baker Prindle calls worth the detour) haven’t sold out.
Before leaving town, visit the effigy mounds that shape Madison’s topography. These low earthen formations, built by Indigenous peoples more than a thousand years ago, were constructed in the shapes of animals, spirits and geometric forms, often as part of ceremonial or burial practices. More than 200 remain across the city.
A few, said Baker Prindle, are especially worth seeking out: Bird Mound, tucked beside the art building at Edgewood College; Bear Mound, set in an oak-shaded park near the zoo; and a cluster behind the University’s Bakke Recreation Center, just off the Lakeshore Path. “They disrupt our sense of time,” Baker Prindle said. “History didn’t just start when white people showed up. It’s been going on for thousands of years.”
The Driftless: Where the landscape shapes the art
For an extra breath of wildness, head to Baraboo’s International Crane Foundation about an hour northwest of Madison. The bird sanctuary is the only place in the world where all 15 crane species live side by side. The grounds stretch wide, with walking trails that pass through reconstructed prairie and wetland habitat.
Or drive straight west to the town of Spring Green, where Frank Lloyd Wright’s Taliesin stands among the rolling hills. Part residence, part laboratory for Wright’s ideas, the property served as the architect’s main home for nearly five decades. It’s also a place scorched by fire, plagued by murder and endlessly remade throughout Wright’s life. Today, guided tours lead visitors through living quarters, studios and stunning grounds.
Following a tour of Taliesin (offered in formats ranging from one to four hours), grab a table at Reunion, a farm-to-table barbeque restaurant set in a restored bank building in downtown Spring Green. The menu leans seasonal and Southern-adjacent: ribs that fall easily from the bone, stone-ground grits and chimichurri-laced asparagus. “The food is so thoughtful, perfect balances of fat and acid,” said artist Jennifer Bastian, who is currently artist-in-residence at the Thurber Park studio in Madison. “It seems like everything comes from somebody’s farm down the street.”
Mineral Point: Galleries, pottery and history
As a final stop, head to Mineral Point, a town dotted with 19th-century sandstone buildings, which was once a hub for miners and merchants. Today, it’s a quiet thoroughfare of galleries, shops and small inns. Among them is Brewery Pottery, housed in a former brewery where a creek still runs beneath the old floorboards. Ask to see the aging rooms, where beer once cooled in the earth’s belly. The space is part studio, part storehouse, part time capsule, with shelves lined with lawn sculptures, hand-thrown mugs and prints by local artists.
Bonus: For a night away, The Birdhouse Inn, just 10 minutes outside Spring Green, offers an unfussy alternative to typical lodging. The small owner-run guesthouse is tucked into a wooded hillside, surrounded by native plants, goats and a guardian dog. Inside, rooms are paneled in pine and decorated with vintage furniture, botanical needleworks and paintings of birds. Breakfast — pancakes, tea and local eggs — is cooked in the open kitchen and handmade soaps. “It looked honestly like I had walked into my own home,” said artist Bastian. “It was so dreamy.”