These 7 Towns In Iowa Have Bustling Main Streets

As a relatively rural state with a low population density, Iowa may not have bustling cities. But it does have towns that bustle in different ways. Rather than stuffy streets and neck-straining skyscrapers, Iowa's towns boast modest but marvelous attractions lining spacious roads that funnel a manageable number of tourists. Whether they're straight, curved, square, or circular, said streets can handle more traffic, so amble on over to ogle the Duke's domain in Winterset, shop at a historic hotel in Elkader, attend a square art fest in Oskaloosa, and do all the quaint activities in between. Join the bustle of small-town Iowa without all the hustle.

Mount Vernon

During the first weekend of May, Mount Vernon has the most colorful main street in Iowa. Roughly 20,000 spectators, 500 artists, and a ton of chalk fill historic 1st Street for Chalk the Walk, Iowa’s first and largest madonnari (Italian-style street painting) festival. Since Mount Vernon has only around 4,500 residents, that is a tremendous feat. Also filling historic 1st Street (for more than just one weekend out of the year) are heritage buildings containing booming businesses. They include Lincoln Winebar in the c.1894-built S. N. Bauman Corner; White Tree Bakery in the c.1869-built W. E. Platner Hardware Store and Tin Shop; and Vintage 1891, LLC in the c.1891-built H. A. Collins Bank/Brackett Building.

Winterset

Ironically, Winterset has all-season charm. This small city, located a few hours southwest of Mount Vernon near Des Moines, decorates its main streets for the Iowa Quilt Festival in spring, the Madison County Fair in summer, the Winterset Festival of Lights in fall, and the Winter Solstice Market to usher in winter. Winterset's main street is called John Wayne Drive, which is fitting since it features the John Wayne Birthplace Museum, which is itself kitty-corner from the John Wayne Birth House. Though Winterset is the birthplace of the Duke, covered bridges are king. Each October, the John Wayne Drive-lined Courthouse Square hosts the Madison County Covered Bridge Festival, which celebrates the surrounding scenic bridges—those that were made famous by Clint Eastwood's movie The Bridges of Madison County.

Pella

Our first chosen community with a main street, actually called Main Street, Pella, is a tight-knit Dutch-based city whose residents routinely gather for cultural events. Chief of those is Tulip Time. Set to have its 90th edition from May 1 to 3, 2025, Tulip Time honors Dutch heritage with more than 300,000 blooming tulips. Aside from smelling flowers, Tulip Timers can tour the Pella Historical Village & Vermeer Windmill and sample authentic Dutch food from Maria’s Tea Room, Central College, and various other vendors. In the evening, they can watch lighted Dutch-themed floats trundle down Main Street, which has its own spectacular sights like Molengracht Plaza's 5,720-square-foot canal! Is it any wonder why Pella is nicknamed "A Touch of Holland"?

Decorah

After touring a Dutch-style main street in Pella, explore a Norwegian-style main street in Decorah. Located in northeastern Iowa, Decorah has a "Main Street," but Water Street is a better candidate for its busiest road. That thoroughfare is overflowing with attractions, ranging from the Kozi Pie Shoppe to Viking State Bank to Vesterheim, the National Norwegian-American Museum, and the Folk Art School. Also worth mentioning is Pulpit Rock Brewing Co., which sits where Water Street branches off into College Drive and crosses the Upper Iowa River. Like Pella, Decorah hosts an annual ode to the Old Country called Nordic Fest. Founded in 1967, this Scandinavian celebration dominates downtown Decorah for three days each summer. Water Street gets absolutely soaked for the Grand Parade, which takes place on the last day of festivities. The next Nordic Fest is scheduled to run from July 24 to 26, 2025.

Elkader

Elkader is a turn-of-the-20th-century time capsule. Only a few roads run through this eastern IA town of about 1,200 people, but its Main Street is lined with marvelous monuments mounted in the late 1800s and early 1900s. They include the Keystone Bridge (c. 1889), Bayless Hotel Building (c. 1897), and Elkader Opera House (c. 1903). Though Elkader is old, it is far from dead. Many Main Street relics have been enlivened by modern businesses and their hip patrons. Open ancient doors, and you'll find camel burgers in Schera's Algerian-American Restaurant, blended espresso-based frappés in GEAR Elkader, and novelty trinkets in the Turkey River Mall (inside the aforementioned Bayless Hotel Building). Main Street is further energized by the annual Elkader Sweet Corn Days, which run in July and honor Elkader and wider Iowa agriculture.

Greenfield

Greenfield's main street is far afield from normal. Instead of a line, Public Square takes the shape of a very imperfect square. This oblong road encircles the c.1892-built Adair County Courthouse as part of the Greenfield Public Square Historic District. On the outer rim of the Public Square stand, among myriad other structures, the Warren Cultural Center (154 Public Square), Grand Theatre & Video (238 Public Square), and Long's Market (106 Public Square). Certain Public Square attractions are preserved with help from the Main Street Iowa branch of the Main Street America Coordinating Program. Greenfield is one of 50-some Iowan members of said program, which is defined as "a common-sense, strategy-driven framework that guides community-based downtown revitalization efforts." In Iowa, "main street" is a nebulous term, but "Main Street" is a strong investment.

Oskaloosa

Another Main Street Iowa community is Oskaloosa, which joined the program in 1986. Since then, over $25.5 million has been invested in 276-plus rehab and renovation efforts to downtown buildings. Beneficiaries include the Mahaska County Courthouse, Book Vault, Trolley Stop Alley, Hunter's, The Office, Smokey Row, True Value, and the Historic Bandstand. It's hard to determine a main street in Oskaloosa since it was built around a square. A Avenue is probably the busiest downtown street, but High Avenue, Market Street, 1st Avenue, and 1st Street host many of the aforementioned sites and frame the lively square. It's even livelier during Art on the Square, which, having celebrated its 55th year in 2024, is one of Iowa's oldest art festivals.

Though it lacks big, bustling cities, Iowa is filled with small, bustling towns—communities that, while low in population, are high in entertainment. Main streets help guide tourists to amazing attractions, sometimes doing so with unique patterns that are attractions unto themselves. From Mount Vernon's chalk-block to Winterset's John Wayne Drive to Pella's waterway to Greenfield's oblong "square," small-town thoroughfares are worthy sights for an Iowa vacation.