7 Prettiest Downtown Strips In Iowa

Not every ideal summer afternoon begins in a large city. Iowa sits between the Mississippi and Missouri Rivers, and six states in the heart of the Midwest. Its towns were founded near railroad crossings, river crossings, mine entrances, and courthouse squares. Most of them still reflect the forces that shaped them. These seven small towns are the center of everything that happens in town, from a cup of coffee to a concert. There are walking-friendly streets, buildings that still tell stories, and events that don’t require a stage to attract a crowd. So if your weekend feels stale, skip the highway exits and drive straight into the square of the prettiest downtown strips in Iowa.

Decorah

You know a town is doing something right when the downtown feels more like a destination than a detour. At Decorah’s center lies Water Street, filled with a brick-red row of storefronts, Dragonfly Books, and locally favorite Agora Arts. Take a break at Impact Coffee, where espresso that is flash-chilled and walls plastered with paintings create a perfect start.

Just a few blocks away, the Vesterheim National Norwegian-American Museum & Folk Art School honors the city’s rich Norwegian heritage. That heritage continues at Nordic Fest and the Nordic Nirvana Festival, with folk dancing, music, and authentic food. Ride the scenic Trout Run Trail from downtown, a loop that circles the city and leads to Dunning’s Spring, where water cascades 200 feet through ferns and limestone.

McGregor

Downtown McGregor is built for wandering. Main Street runs between the Mississippi and limestone bluffs, where stores like By the Spoonful and Paper Moon stock toys, used books, and gourmet jam in creaky 19th-century buildings. A few doors down, the McGregor Historical Museum occupies a converted hardware store filled with artifacts from the steamboat era.

Hike to Pikes Peak State Park for bluff-top views, then descend into the depths of Spook Cave, where boat tours float through eerie rock formations. Visit in September during the Scottish Heritage Festival, when bagpipes echo down the street and the Kilt Contest fills downtown with music, laughter, and a few bold outfits.

Mount Vernon

You don’t expect much from a town this size until you step onto 1st Street. Preserved storefronts include longtime fixtures like Bauman’s, open since 1909. Vintage 1891 Antiques & Collectibles is a slow-walk-worthy trove packed with vinyl, signage, and curios you didn’t know you needed.

Every May, over 500 chalk drawings fill the sidewalks during the annual Chalk the Walk festival, drawing big crowds and bright colors. Around the corner, the First Street Community Center houses galleries, indie merchants, and a black box theatre. Just beyond town, the American Gothic Barn features the iconic painting recreated on the side of a barn among fields of corn.

Elkader

You don’t need a map in Elkader. Just follow the curve of the streets. Start on Main Street, where limestone storefronts lean toward the river and the Turkey River Mall sells antiques, vinyl, and Midwestern nostalgia. Break for lunch at Schera’s Algerian-American Restaurant, one of the only places in Iowa where you can try lamb tagine and harissa potatoes.

Catch a show at the Elkader Opera House, a 1903 gem hosting concerts, plays, and film nights. Visit in July for Sweet Corn Days, when downtown overflows with food, live music, and buttered corn. Afterward, rent a kayak and float the Turkey River Water Trail, drifting beneath bridges and along shady backyards.

Pella

The best way to see Pella is to start walking in any direction from the square. It takes you past red brick buildings and straight into Jaarsma Bakery, where Dutch letters and almond bars often sell out before noon. Steps away, the Vermeer Windmill towers over the Pella Historical Village, surrounded by canal facades, tulip gardens, and antique shops.

Head past that to Molengracht Plaza, a Dutch-style pedestrian zone with fountains, benches, and gelato. In July, join Thursdays in Pella, when downtown fills with music, lights, and late-night crowds.

Winterset

This town feels familiar, even if you have never been. Maybe it is the movie-poster charm of the square. Begin at the Madison County Courthouse, a sandstone focal point among peaceful streets. Walk into Piece Works Quilt Shop, a colorful patchwork of patterns and hand-dyed fabrics. Across the street, the Iowa Quilt Museum rotates exhibits exploring traditional and modern fiber art.

Venture into Winterset City Park, where the Cutler-Donahoe Covered Bridge crosses a wooded path leading up to Clark Tower, a limestone lookout built for daydreaming. Visit in October to catch the Covered Bridge Festival, with live bluegrass, local booths, and all the photo ops your phone can handle.

Fairfield

Fairfield’s downtown has a rhythm all on its own. Begin in Central Park, where Fairfield First Fridays and Live on the Square bring out food vendors, art displays, and live performances. Wander through the square, which is filled with international restaurants, galleries, and local gems like At Home Store, which is known for its sustainable goods and artisan finds.

Stop at the Fairfield Farmers Market on Wednesdays or Saturdays to pick up produce and sample homemade specialties. Then visit the ICON Gallery, home to boundary-pushing art exhibits. For open-air time, follow the Fairfield Loop Trail as it skirts the Maharishi International University (MIU) campus and offers views of domes, gardens, and quiet woods.

Main Streets Worth the Miles

There are plenty of small towns in Iowa, but only a few manage to get their downtown just right. These are towns where the post office remains a part of daily life, where summer evenings linger on the sidewalk, and where no one is in a hurry to send you on your way. There are courthouse squares that draw you in, sidewalks built for wandering, and storefronts that look lived in, not staged. It might be a porch concert or a bakery with a real line. These towns make you want to linger a little longer. You won’t need a guide. Just walk until something draws you in, and let Iowa take it from there.