These 9 Towns In Iowa Have The Best Main Streets
Iowa has some quirky boasts, including the largest ethnic heritage museum in America, the invention of the first bread-slicing machine, and the original grower of Red Delicious apples. Iowa also raised the first female lawyer, a Broadway musical writer, and a famous hero of the Old West. That eclectic mix of firsts and fame is sure to lead to some pretty intriguing stops throughout the state. These nine towns in Iowa have the best main streets where you can discover the state's history, best-kept secrets, and natural beauty.
Winterset

Located in Madison County, one might say Winterset actually has four main streets sharing prime real estate overlooking the town courthouse. The 1876 building is an architectural showstopper, with its elegant domed clock tower and imposing columns. Several other historic buildings lining the town square are home to some of Winterset’s best shopping and eateries. The classic taproom, The Drift, is a town gathering place where guests sample craft beers and comfort food overlooking the square. Cozy booths are made for leisurely sipping and tasting menu favorites, including shareable appetizers, classic sandwiches, and a killer Sunday Brunch.
If you live for the next great vintage find, Pine Creek on the square is a fun place to shop for a mix of new and antique furnishings. Get lost browsing the catchall of wonderful wares ranging from home décor and art to cooking tools and fashion. The town’s main claim to fame is the bridges of Madison County with their iconic red siding and timber construction. With most too weather-worn to support the weight of vehicles, visitors are welcome to snap a selfie and cross the bridges on foot or by bike. Finally, take in the views of the Middle River Valley from the historic two-story limestone Clark Tower. The striking Winterset landmark looms twenty-five feet above City Park like the ruins of an ancient castle.
Decorah

Decorah sits along the Upper Iowa River. The hilly country, rivers, and bluffs attract outdoor enthusiasts and adventurers, while the downtown’s 100-plus-year-old historic district is known for the eclectic shops and eateries along its main street. Bookworms head to Dragonfly Books to browse shelf after shelf of titles across all genres. Check out their events calendar to see if any authors are in town while you are there.
Discover the magic of the Driftless region on the trails at Dunning’s Spring Park and Ice Cave Hill. Walk to the waterfall surrounded by limestone cliffs, cross the stone bridge, and explore the ice-covered walls, even in the heat of summer. To warm up, find a cozy corner at Magpie Café & Coffeehouse for a hot cup of Irish Coffee spiked with whiskey, then explore the town’s Norwegian heritage at Vesterheim, the National Norwegian-American Museum and Folk Art School. Wander the park’s historic buildings or explore the collection of folk art and interactive exhibits.
Pella

Find yourself transported to the Netherlands in Pella. Stroll the Molengracht Plaza along a replicated Dutch canal lined with cobblestone accents, charming lampposts, and flower-filled urns, reflecting the town’s heritage. Set your watch to visit the Klokkenspel, where eight 4-foot mechanical figures portray moments of Pella’s history. There are five performances running every two hours, starting at 11:00 a.m. Don’t miss the courtyard behind the Klokkenspel, where you will find quaint flowerbeds and lovely Dutch tile scenes nestled in arched niches.
You can also tour the inner works of the Vermeer Windmill, where you can watch the massive blades and climb the steps to take in the view. The authentic 1850s-style "koren mill" was built in the Netherlands and reassembled in Pella as a nod to the traditional grain mills central to small Dutch towns. While there, explore the Miniature Dutch Village, where charming scenes depict life in the 1800s. Complete your visit with a scrumptious Dutch "koffie tijd" at Maria’s Tea Room in the historic Scholte House. The traditional coffee break is akin to an English tea, with assorted savory and sweet treats.
LeClaire

Lovely LeClaire’s Cody Road offers picturesque views of the Mississippi River. Named after William “Buffalo Bill” Cody, the mix of homes and businesses balances restored mid-to-late 19th-century character with modern accents, creating a rustic-chic feel. "Libation Lane" serves up three tempting tipples with your choice of wine, craft beer, and spirits.
The taproom at Green Tree Brewery combines the best of two worlds with a selection of craft-made beers and coffee-infused concoctions. The friendly atmosphere is contagious, making it hard to pull yourself away from your flight to move on to your next stop. Mississippi River Distilling Company is a brother-owned micro-distillery specializing in vodka, gin, and bourbon made from locally sourced grains. Their Cody Road Cocktail House introduces you to what may very well become your brand of choice after sampling their custom craft cocktails and flights. They also serve cheese tastings from Cinnamon Ridge Farms. Meanwhile, wine connoisseurs can find a seat in the quaint courtyard at Wide River Winery. The cleverly named wines are a hint at the winemaker's past as an attorney. Spend the afternoon lingering over yummy small bites paired with their selection of wines.
While the main street has a collection of antique and vintage shops, in-the-know antiquers take a detour to Antique Archeology. The home to the History Channel’s American Pickers is a must-visit destination for die-hard treasure hunters.
Clear Lake

Clear Lake hugs the banks of its namesake, a freshwater lake and main attraction for Clear Lake State Park. While the sparkling waters are a major town draw, the gift shops, cafés, eateries, and fashion boutiques along the main street give the lake a run for its money. Browse the work of local and regional artists at the Clear Lake Arts Center and the most recent works in the center's Sukup Lakeside Courtyard and Sculpture Garden. Whether you find a spot on the town beach, head to the peaceful acreage at the park, or spend hours fishing, water skiing, or windsurfing, Clear Lake is a summer paradise for water activities or lazy days tanning.
Any time of year, the cozy house setting at Lake Time Brewery is just what you need after a day exploring. Grab a picnic table on the lawn to sample their selection of craft-made beers on tap, starting from light to dark, to enjoy the increasing intensity of flavors. Then, head to the legendary Surf Ballroom, where rock heroes Buddy Holly, Ritchie Valens, and J.P. “The Big Bopper” Richardson played their last concert. The ballroom continues the tradition of presenting exceptional performances, earning its place as one of America’s premier live venues. While there, be sure to check out the ballroom’s latest edition, where the birth of rock ‘n’ roll comes to life through an immersive, one-of-a-kind rock ‘n’ roll exhibit.
Mount Vernon

Mount Vernon is home to Cornell College, with its beautiful campus set against the hills of Linn County. The college town’s historic main street is filled with 19th-century architectural detailing, such as lovely arched windows and ornate cornice-topped rooflines. Kick off your visit with a cup of coffee at the eclectic Fuel Art & Espresso. The aroma of fresh-roasted coffee, mismatched vintage furniture, and a collection of global finds invites guests to take their time sipping coffee, nibbling artisanal pastries, and admiring the wares. Grab a coffee to-go and take a walk through the Cornell College Historic District. The imposing King Chapel stands guard over the beautiful buildings, lovely mature trees, and well-manicured lawns.
In September, the downtown district hosts the annual Lincoln Highway Arts Festival, where artists gather to share their work and art lovers flock to discover rising talent. Live music, artists at work, and local eateries contribute to the creative spirit that flows through the community. The fertile farmland in Mount Vernon’s backyard is also worth exploring. Kroul Farms is open year-round, where the Kroul family has been working the land since 1946. Now a modern marketplace celebrating the bounty of the seasons, there is always something to taste, learn, and discover at the farm.
Elkader

Located in Iowa’s Little Switzerland region, Elkader is tucked away in a scenic valley on the Turkey River. Even the historic downtown district on the main road has views of the rolling green hills. A mix of brick and limestone façades speaks to the town’s storied history. One of Elkader's best features is the Keystone Bridge, spanning 346 feet, supported by two charming arches. Made of locally quarried limestone in 1889, it offers lovely views of the river and treelined banks. The Elkader Opera House is a main street landmark with its early 1900s red brick detail and arched windows. Experience a live performance in the vintage theater and admire the classic horseshoe balcony and stunning ruby glass chandelier.
Follow the meandering trail at Pony Hollow along an old railway bed. The riverside trail is popular with hikers, cyclists, and horseback riders who appreciate the shady trees, flat terrain, and peaceful scenery. Despite its location in Little Switzerland, Elkader has indirect ties to Algeria, named after Algerian freedom fighter Abd el-Kader. It is also the sister town to Mascara, Algeria. These links inspire the exceptional Algerian food at Schera’s Restaurant. A mix of Algerian, Mediterranean, and Midwestern cuisine includes the intricate flavors of the rich couscous stew, Berkoukes, and the trendy poached egg sensation, Shakshuka, to name a few.
McGregor

McGregor is nestled between the Mississippi River and sandstone bluffs that transform into vivid color in the fall. The compact historic main street faces a tiny park surrounded by red brick sidewalks. The unusual townscape is made for leisurely strolls, window shopping, and lingering lunches on chilly fall days. Discover emerging artists and unknown talent at the Left Bank Shop & Gallery. When you find a work that moves you, the majority of your purchase goes to the artist, whether it is a whimsical hand-drawn card, jewelry, ceramic and glass pieces, or framed paintings and photographs. Explore the antiquarian treasures of Rivertown Fine Books, where used, scarce, and rare titles are sold alongside an eclectic mix ranging from pre-Civil War maps to original art and pre-WWII toys. The family-run shop is a wonderful main street find with its antique cash register, wooden cabinets, and vintage glass cases.
When it's time to refuel, visit the cozy gourmet food boutique, By the Spoonful, to stock up on Iowa-made specialties from wine and craft beer to locally sourced meats and homemade take-&-bake meals. Grab a coffee at the espresso bar and lunch from their deli selection for a picnic at Pikes Peak State Park. Hike the trails, taking in the beauty of the bluffs, valleys, and mighty Mississippi. A short half-mile path leads to the lovely Bridal Veil Falls, where you can find a quiet spot to relax and enjoy your picnic lunch.
Mason City

Mason City beckons architecture fanatics to its Rock Crest-Rock Glen Historic District, where Wright on the Park offers tours led by knowledgeable and passionate docents. The district’s collection of Prairie-style homes includes those of Frank Lloyd Wright, Walter Burley Griffin, William Drummond, Francis Barry Byrne, and Curtis Besinger. The Historic Park Inn Hotel is the world's last remaining hotel designed by Frank Lloyd Wright. Built in 1910, it has been restored with full respect for the remarkable legacy of the famed architect’s work. It is a dreamy choice for an overnight stay, or at the very least, worth a visit to admire the gorgeous lobby.
Mason City is also home to Robert Willson, the creator of the popular musicals The Music Man, The Unsinkable Molly Brown, and Here’s Love. Music Man Square is a 1912 streetscape and replica of the movie set, and the museum and Meredith Willson’s family home offer an engaging look at the composer’s life. Sample the goods at Birdsall's Ice Cream, where they have been pleasing young and old with their frozen sweet treats since 1931. The vintage ice cream parlor serves up classics, including banana splits and refreshing root beer floats. Choose from dozens of flavors and seasonal favorites served in a cup, cone, sundae, or shake, and you will surely leave Mason City with a smile.
The qualities that rank the main streets in Iowa's best small towns vary from their character-filled architecture to their unique eateries, and from their cultural experiences to their history. Whether you are due for a well-deserved weekend escape, are in the mood for an Iowa road trip, or are up to discovering some local haunts, these nine best main streets in Iowa deliver unique experiences.