June 12, 2024

IOWA Main Street and Town Square Bracket Challenge- SWEET 16

Following a fun debate at work about town squares in my own region, I decided to create a bracket of 64 for Main Streets and Town Squares in Iowa. These Main Streets and Town Squares have been the center of commerce, life and history for these communities across the state.

Due to the sheer number of towns to start, I decided to wait until we reached the Sweet 16 round to truly give these communities a showcase. All polling has been done through the Twitter polling feature, and hyperlinks will be available below.


Travis Halm | The Tailgate Society

#1 Harlan vs #4 Carroll

Historic Shelby County Courthouse
The Shelby County Courthouse, the cornerstone of the Harlan Town Square. Photo Courtesy of TravelIowa.com

Harlan defeated #16 Corning and #9 Red Oak to reach the Sweet 16. Harlan’s Town Square is anchored by the Shelby County Courthouse and features a full square with historic buildings, a theatre, restaurants and a floral shop.

Confluence | Detail
Main Street in Carroll, Iowa, an economic hub for West-Central Iowa. Photo Courtesy of ThinkConfluence.com

Carroll defeated #12 Cherokee and #5 LeMars to reach the Sweet 16. Carroll’s downtown area is a retail and commercial hub for West-Central Iowa and its smaller outlying agricultural communities.


#3 Atlantic vs #7 Spencer

Downtown Atlantic, Iowa | Atlantic is located in the southwe… | Flickr
Main Street, Atlantic, Iowa, Courtesy of Courthouselover on Flickr

Atlantic defeated #14 Guthrie Center and #11 Denison to reach the Sweet 16. The home of Coca Cola distribution in Iowa, and the county seat of Cass County has a five-block long historic commercial strip along Main Street, anchored by a town square and a train station.

Traffic passes through downtown Spencer, Iowa, on Thursday, June 22, 2017. A fire in 1931 destroyed several downtown buildings.
Main Street, Spencer. Courtesy of the Des Moines Register

Spencer defeated #10 Sheldon and upset #2 Clarinda to reach the Sweet 16. The largest collection of art deco buildings in the state exists in Spencer due to a massive fire downtown due to a fireworks accident. Most buildings along Spencer’s Main Street were destroyed and rebuilt in this architectural style following the 1931 fire.



Travis Halm | The Tailgate Society

#1 Winterset vs #5 Clear Lake

The Madison County Courthouse centered in the Winterset Town Square. Photo courtesy of MadisonCounty.com

Winterset, the Madison County seat, defeated #16 Montezuma and #9 Nevada to reach the Sweet 16. Winterset is known to be the birthplace of John Wayne, the home of the Covered Bridge Festival, and has a well-preserved town square centered by the Madison County Courthouse.

Downtown Clear Lake along the shores of Clear Lake. Photo Courtesy of Anthony Djuren Fotography.

Clear Lake’s Downtown lies along the shores of Clear Lake, a popular tourist and boating destination in North Central Iowa. This Main Street includes a city park, views of the lake, and the famous Surf Ballroom.


#2 Grinnell vs #6 Adel

Downtown Grinnell, Iowa. Photo courtesy of the Grinnell Chamber of Commerce.

Grinnell is home to Grinnell College and reached the Sweet 16 by knocking off #15 Osceola and #10 Algona. This college town has a bustling town square with unique architecture, numerous shops and restaurants which are staples for the college and the community.

Statue located on the Dallas County Courthouse in Adel. Photo courtesy of DiscoverAdel.com

The home of Heisman winner Nile Kinnick and the Dallas County Seat, Adel beat #11 Grundy Center and upset #3 Newton to reach the Sweet 16. Adel features an impressive county courthouse which centers its town square.



Travis Halm | The Tailgate Society

#1 Decorah vs #4 Waverly

Main Street Decorah, photo courtesy of Joyce Meyer and Winneshiek Development Corporation.

Nestled in the driftless region of Iowa and home of the famous Toppling Goliath Brewery, top seeded Decorah beat #16 Bellevue and #9 Dyersville to reach the Sweet 16. Decorah is home to Luther College and has a bustling Main Street which is a regional staple and economic driver for the region.

Sidewalk sale time along Bremer Street in Waverly, photo courtesy of TravelIowa.com

Located north of Waterloo-Cedar Falls, Waverly is home to Wartburg College and beat out #13 Traer and #5 Maquoketa to reach the Sweet 16. This Main Street serves students and residents of Waverly as the commercial hub of the community.


#3 Charles City vs #7 Anamosa

The Cedar River and Downtown Charles City, photo courtesy of the Walking Tourists.

Charles City defeated #14 Osage and #11 Independence to reach the Sweet 16. Charles City’s central business district features a healthy mix of historic and new buildings which enrich the character of this river-adjacent commercial district.

An old clock marks lunchtime in Downtown Anamosa, Iowa. Photo Courtesy of J. Stephen Conn via Flickr.

Anamosa’s Main Street beat #10 West Union and upset #2 McGregor to reach the Sweet 16 in the Northeast region. This Main Street is the cornerstone of a community most known for being home to the historic penitentiary a few blocks west.



Travis Halm | The Tailgate Society

#1 Pella vs #4 Oskaloosa

Pella ranked #19 Top 100 Best Small Towns - Livability
Downtown Pella, Iowa with the Town Square tower and windmill in the distance. Photo Courtesy of Livability.com

Home to the famous Tulip Festival, numerous Dutch bakeries and restaurants, and the home of Central College, the Pella Town Square is a favorite among people from around the State (and around the world). This predominantly Dutch-reformed town is true to its roots, and the Pella Town Square is the centerpiece of this community. Pella knocked off #16 Marengo and #9 Williamsburg en route to the Sweet 16.

Travis Halm | The Tailgate Society The Oskaloosa Bandshell on the Oskaloosa Town Square. Photo courtesy of OskyNews.com

Oskaloosa, a true rival of nearby Pella, knocked off #13 Tipton and #5 Centerville to reach this matchup with their neighboring foe. The Oskaloosa Town Square features a bandshell and the nearby Mahaska County Courthouse. Storefronts are also known to be completely covered in lights come Christmas-time.


#2 Albia vs #14 Mount Vernon

Skean's Block (Albia, Iowa) | This is one of the beautiful s… | Flickr
Skean’s Block in Albia. Photo Courtesy of Courthouselover/Flickr

#2 Albia defeated #15 Keokuk and #7 Washington to reach the Sweet 16. Their town square has many preserved buildings from the 1890s in their original detail and form, making this one of the more popular small town squares in the state.

“Chalk the Walk” in Mount Vernon. Photo courtesy of Cornell College.

#14 Mount Vernon has been the Cinderella of this tournament, upsetting both #3 Fairfield and #11 Knoxville. Mount Vernon is the home of Iowa’s Cornell College, and the small yet vibrant community has numerous events on their main commercial strip, including Chalk the Walk above.


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Travis Halm
Travis Halm 43 Articles
Staff Writer

Travis Halm is an Iowa State Alum living in Omaha, Nebraska. A native of Haverhill, Iowa, Travis has lived throughout the Midwest and in Texas, providing him insight on the Big 12, the SEC, and a wide variety of other sports topics. Travis follows the Cyclones closely, in addition to the Cardinals, Packers, Texas A&M and rarely turns down a ticket to a good sporting event.

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