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9 Midwest Must-Visits from Enchanted Highways to Winter Art Crawls 

by Amy Felegy

A sculpture of birds, an orange circle and hills against a blue skuy.
Photo Credit: Courtesy Enchanted Highway Facebook
"Geese in Flight" kicks off North Dakota's Enchanted Highway, beginning on I-94's exit 72. Mile 0 – Geese in Flight

Here’s your excuse to traverse the Midwest—in pursuit of cool art happenings! With your help, we compiled an array of bucket-list travel spots across the region with artsy ties. 

It’s impossible to hit every neat-o spot on the Midwest map when it comes to art destinations. But we did our best to find one in each state we think is travel-worthy, thanks to help from readers.

Look no further for your guide to all things wacky, theatrical, and artsy galore.

‘Indiana’s Nicest Day’ 

The Penrod Arts Fair means 400 booths, live music, food, and beer. It’s been alive since the 1960s outside the Newfields museum grounds in Indianapolis, Indiana. Organizers call it one of the biggest single-day art fairs in the U.S. 

‘House of a Thousand Dreams’

Imagine the brightest colors you can. Now imagine them even brighter. The Immersive Art Fun House in Fairfield, Iowa, is home to artist Tom Lassota’s 20-years-in-the-making walk-through display that truly puts the fun in fun house. 

Artist Haven

Ask any local what Makanda Village is, and odds are you’ll hear something about art. The small Illinois community is home to many artists and is often called Valley of the Arts, with its annual Vulture Fest and countless galleries and studios for visitors to peruse.

We’re Not in (Ohio) Anymore

An old OfficeMax store turned truly bizarre, immersive trip Otherworld is, well, otherworldly. The Ohio bucket-list item has 50 rooms and different storylines meant to make you feel like you’ve truly left Earth.

An art installation depicting a room with glow-in-dark decorative accents and light fixtures. There is a walkway through a tree stump-like work.
Photo Credit: Courtesy of Otherworld
The Forest, an installation experience at Otherworld located near Columbus, Ohio.
Actors wearing costumes gather on stage in dark lighting.
Photo Credit: Courtesy Interact Facebook
Interact Center for the Visual and Performing Arts puts on shows throughout the year, aiming to “challenge perceptions of disability.”

Art from Your Car Window

Fancy a road trip? Over 30 miles of sculptures are scattered along the road across North Dakota’s Enchanted Highway, from the world’s biggest tin family to Theodore Roosevelt riding a horse. It’s all wheelchair accessible with audio tour options.

Bookworms Unite

South Dakota’s Festival of Books is for all the bibliophiles out there. This year, authors and readers gather in Spearfish for signings, big ol’ book clubs, and panel discussions galore. Read on!

Art for All

Over 100 artists work at Interact Center for the Visual and Performing Arts, whether it be painting, dissecting a script, or working a loom. The St. Paul, Minnesota, non-profit caters to artists with disabilities and the wider area looking for a show, a print, or community.

Celebrating Black Culture

Awaiting to fully open, the Museum of Black Experience in Saginaw, Michigan, established a brick and mortar building in 2023. Inside is an artist-in-residence space, gallery and reflection area, a library, and a reading room. 

Mid-Winter Art Crawl

Coming up in February is Eau Claire’s Banbury Art Crawl—we’re talking all the art, food, live music, and demonstrations. The free-to-attend Wisconsin event has been running since 2008 and includes over 100 artists and vendors, from woodworking to stained glass.