8 Most Charming Town Squares In Iowa
There’s something special about a good small-town square, and the Hawkeye State has plenty worth exploring. While Iowa might be known for its rolling farmland, cornfields, and big skies, it’s the close-knit communities that define it. Town squares here aren’t just a patch of grass with a courthouse—they’re where the town comes to life. From Dutch-inspired storefronts to historic opera houses, these squares are full of character, stories, and places that make you want to stay a little longer. Here are eight of the most charming town squares in Iowa—each with its own flavor, a few local gems, and a whole lot of small-town heart.
Winterset
Winterset, the seat of Madison County, has a walkable, lived-in town square that is very much the center of town. Founded in 1849, the town was initially called Summerset, but a surprise cold spell inspired the name change to Winterset. At the heart of it all stands the Madison County Courthouse, a sturdy limestone building from 1876 with a clock tower that rises above the Square and sets the tone for everything around it.
The courthouse lawn has wide sidewalks and benches, often with locals taking a break or chatting with neighbors. Just across the street is the Iowa Quilt Museum, a thoughtful space featuring rotating exhibits that celebrate quilting as both art and tradition. A few steps away, the Piece Works Quilt Shop draws in crafters from around the state with its wide selection and helpful staff.
A short walk from the Square brings you to the John Wayne Birthplace Museum, which highlights the town’s most famous native son. The museum has extensive memorabilia, movie props, and personal items from the Duke’s life, and it draws a steady stream of visitors year-round. Independently owned shops, cafés, and lunch spots—many in restored buildings that date back more than a century line the Square.
Pella
Pella's town square is ringed with Dutch-style architecture and red-brick storefronts, reflecting the town’s deep-rooted Dutch heritage. Founded in 1847 by immigrants seeking religious freedom, Pella has held tight to its cultural identity—and nowhere is that more visible than in its vibrant central Square.
The streets around the Square are home to locally owned bakeries, shops, and specialty stores, many of which follow traditional Dutch design. One must-stop is the Jaarsma Bakery, where the scent of fresh Dutch letters, almond cookies, and strudel spills out onto the sidewalk. You can grab a pastry and enjoy it on a bench in Central Park, the town green at the Square’s center, which often hosts live music, small festivals, and community gatherings.
Just off the Square stands the Vermeer Windmill, the tallest working windmill in North America, built using traditional methods and materials from the Netherlands. You can tour the interior and even climb up into the mill itself for a view of downtown. Another nearby highlight is the Pella Historical Village, where a collection of preserved buildings tells the story of the early Dutch settlers and how they built the town from the ground up. Pella’s Square offers a thoughtful mix of history, culture, and small-town rhythm—easy to enjoy, and hard to forget.
Eldora
Eldora sits in the middle of the Iowa River Valley with a downtown square that feels like it hasn’t rushed to catch up with the times—and that’s part of the charm. Established in the 1850s, Eldora grew as the seat of Hardin County, and its historic Square still reflects the town’s early prosperity. At the center is the impressive Hardin County Courthouse, built in 1892, with its tall clock tower and sandstone detailing giving it real presence among the surrounding buildings.
The square boasts well-kept storefronts dating back to the late 19th and early 20th centuries, many of which still house local businesses. You’ll find friendly spots to grab lunch or browse antiques, with shopkeepers happy to swap stories or point you to nearby sights. One of the best is the Eldora Social Club, a unique Greek and Italian pizza joint that is a popular local hangout. Just off the Square, the Eldora Welcome Center and Railroad Museum offers a look into the area’s railroading roots and pioneer past. It’s a small but well-curated space, and a good starting point for getting to know the town.
Seasonal events keep the square active, from farmers' markets in the summer to light displays in December. If you are feeling adventurous, hike the 2.5-mile trail from Eldora to Pine Lake State Park. This state park is a hidden gem with deep ravines and peaceful lake views. Whether you’re sitting under the shade trees outside the courthouse or poking around in a quiet bookstore, Eldora’s Square gives you room to slow down and enjoy a more relaxed pace—no frills, just the good stuff.
Bloomfield
Bloomfield’s town square is a well-preserved piece of the past that pulses with daily life as the heartbeat of the community. Founded in the mid-1800s, Bloomfield quickly became the center of Davis County, and its downtown reflects that legacy. The standout feature is the striking Davis County Courthouse, completed in 1877. With its mansard roof, central clock tower, and Second Empire-style architecture, it remains one of the most distinctive courthouses in the state.
Around the courthouse, the Square has roughly 50 historic commercial buildings—many dating back to the late 19th century. The block features brick storefronts with original details like arched windows, decorative cornices, and pressed tin trim. The businesses here are still going strong, from boutiques like Clover and Bloom to diners like CJ's Family Restaurant serving up comfort food with a side of conversation. The Davis County Historical Museum is open on Saturdays during the summer and features memorabilia and artifacts from the local region.
The courthouse lawn plays host to seasonal festivals, summer concerts, and small-town parades that draw folks from miles around. It’s common to see lawn chairs lined up for evening events or kids racing each other around the sidewalks while parents chat on benches. Bloomfield’s Square is the kind of place where you can grab a slice of pie, poke through a secondhand shop, and lose track of time in the best possible way.
Greenfield
Greenfield may be small, but its town square leaves a big impression. Laid out in 1856, the Square still follows its original Lancaster-style plan, with streets radiating outward from a central block. At its core stands the impressive Adair County Courthouse, built in 1891. With its Romanesque arches, tall clock tower, and decorative stonework, the courthouse anchors a square that feels like the real heart of the community.
One of the highlights of the Square is the restored E.E. Warren Opera House, now home to the Warren Cultural Center. This beautifully preserved 1896 building hosts concerts, theater performances, art shows, and community events in a space that’s both elegant and down-to-earth. A few steps away is the Hotel Greenfield, a 1920s gem that has been brought back to life with period-style furnishings and a cozy, welcoming atmosphere. Even if you’re not staying the night, it’s worth stepping inside to admire the craftsmanship.
You’ll also find Ed & Eva’s, a gallery and gift shop connected to the cultural center that features handmade goods from Iowa artisans—everything from pottery and jewelry to folk art and textiles. Local cafés, a vintage movie theater, and small boutiques round out the Square, giving it the kind of variety that makes wandering easy and enjoyable.
Harlan
Harlan’s courthouse square has a solid, grounded feel—built to last, and still very much in use. Founded in the 1850s, Harlan became the county seat of Shelby County and grew steadily through the late 19th century. The town’s centerpiece, the Shelby County Courthouse, was built in 1893 and stands tall with its rounded Romanesque arches, turrets, and a central tower that gives it a fortress-like quality. It’s a striking building that sets the tone for the rest of the Square.
Surrounding the courthouse are rows of brick commercial buildings, most dating from the late 1800s to early 1900s, and many still housing local businesses that have been here for generations. On any given day, you’ll find residents stopping into Milk & Honey, a popular café just a block from the Square, or browsing antiques at Bigfoot Sales, which offers everything from vintage signs to old-school vinyl. It’s the kind of place where each storefront has a story—and likely a friendly face behind the counter.
The Shelby County Civil War Memorial standing on the courthouse lawn, is a quiet reminder of the town’s history and the people who shaped it. Community events, like live music nights and sidewalk sales, give the Square a lively energy during the warmer months. This small town square is classic Americana, and that is precisely how it ought to be.
Centerville
Centerville has a town square that the locals proudly call the “World’s Largest Town Square,” and while that claim might be up for debate, there’s no denying the Square is impressively big, well-kept, and packed with personality. The Square stretches across two city blocks on each side, with more than 100 historic buildings adding to the ambiance.
At the heart of it all is the Appanoose County Courthouse, a Romanesque-style building, first erected in 1904. The old Continental Hotel is now home to Lucile’s, a local favorite known for hearty breakfasts and strong coffee. Around the Square, you’ll find a mix of antique shops, small boutiques, and hometown businesses. Art lovers will appreciate the Majestic Theater, a beautifully restored 1930s movie house that now hosts plays, live music, and community events.
Centerville’s Square also shines during seasonal festivals and Saturday markets. In summer, it’s common to see classic cars lined up along the curbs, local musicians playing from the bandstand, and families enjoying the open space. There’s a rhythm to this place that makes it easy to settle into—you can shop a little, eat well, catch a show, or walk the loop and take it all in.
Decorah
Decorah’s downtown square is the cultural and social hub of this scenic town tucked into the northeast portion of the state. As the seat of Winneshiek County since the early 1850s, Decorah’s Square grew alongside the town’s Norwegian roots, its riverside setting, and a strong sense of local identity that still defines the place today.
At the center of it all is the Winneshiek County Courthouse, a stately Neoclassical building with tall white columns, a grand staircase, and a four-faced clock tower. This Square enjoys shade trees, a miniature replica of the Statue of Liberty, and a Civil War memorial that gives the Square a sense of quiet pride. The streets around the courthouse have handsome brick buildings—most over a century old—that house everything from restaurants and gift shops to bookstores and boutiques.
One of the standout spots along the Square is the Rubaiyat Restaurant, a popular American bistro serving seasonal fare in a circa-1890 building. Just a short walk from the Square is the Vesterheim Norwegian-American Museum, which features a collection of historic buildings, folk art, and exhibits that celebrate Decorah’s deep immigrant roots.
Churches from different traditions anchor the corners of the Square, each with its architectural style and long history in the town. And while the buildings are beautiful, it’s the sense of community that truly defines the space.
Charming Town Squares in the Hawkeye State
Iowa’s town squares embrace community connection. Whether it’s a courthouse lawn where neighbors gather for summer concerts, a family-run bakery that’s been in business for generations, or a museum tucked into a former schoolhouse, each of these squares tells a story about the town that surrounds it. What makes them charming isn’t just the architecture or the history—it’s the way they embody the close-knit connections residents love. So next time you’re driving through the Hawkeye State, take a turn off the highway and spend a little time in one of these downtowns. You’ll find good coffee, maybe a new favorite shop, and a place that feels right.
