Oskaloosa Walking Tour Preview

City Square and Bandstand

Oskaloosa's City Square, officially known as City Square Park, serves as the historic and cultural heart of the city. Established in 1844 as part of the original town plat, the square has evolved into a central gathering place for residents and visitors alike.A prominent feature of the park is the bandstand, designed by architect Frank E. Wetherell and constructed in 1912. This 29-foot-high octagonal structure, made of concrete, iron, and steel, hosts daily music performances and community events.The square is also home to several historical monuments, including a statue of Chief Mahaska, dedicated in 1909, and a Spanish-American War torpedo.Throughout the year, City Square Park hosts various community events, such as Art on the Square, Sweet Corn Serenade, and the Lighted Christmas Parade, which features over 300,000 Christmas lights illuminating the area.Today, the square remains a vibrant center for shopping, dining, and cultural activities, reflecting Oskaloosa's commitment to preserving its heritage while fostering community engagement.

Brown's Shoe Fit Co.

You can buy a pair of shoes just about anywhere... but if you want quality and variety, join our loyal customers who always come back for the brands they know by name and the excellent customer service they receive. At Brown’s Shoe Fit Oskaloosa, we offer shoes for the whole family: men’s, women’s, and children’s. We’re proud to offer you the LARGEST selection of athletic shoes and work boots in South central Iowa! If you want it, we’ve got it! We have the perfect shoe for any occasion, whether you’re looking for something business casual, a shoe to run in, work in, or just something casual!If you are looking for professional service and comfortable shoes that fit, visit us today in downtown Oskaloosa, our home since 1962.

Book Vault

Trolley Place

The first horse drawn street car in Osky was converted to electric trolleys in 1897. Three buildings were named Trolley Place since it is where the trolly lines crossed until 1925 when they were replaced by buses. The three buildings are Fitch (114), McGregor (116-118), and Malcolm (120) where there have been at least two major fires.

Oskaloosa Art Center and Studio

Explore the creativity of Oskaloosa artistry and Music at the Oskaloosa Art Center and Studio. FACE has been running the Oskaloosa Art Center & Studios since 2014. It includes a professional gallery, with changing exhibits (currently hosting a ceramics exhibit), a classroom, a ceramics studio, and The OuterSpace, a performance venue. The Art Center hosts classes, workshops, including Art Uncorked, a monthly wine and painting event and Creative Juices, a painting event for kids. FACE hosts the Oskaloosa Sculpture Tour that can be found on Otocast.

The Alley

The Alley project is a show of true passion for community development and beautification. A group of women who call themselves the Alley Kats (Kats after the initials of their last names. Also, they call their husbands the Tom Kats) came up with this plan, raised the money, and here we are. The alley was once nothing more than a vacant, crumbling, ugly alley. Now it’s a beautiful place to sit, enjoy and relax. On Thursdays in July and August, various businesses and organizations sponsor Thankful Thursdays from 6-8 and offer free wine, beer, and music. Then at 8:00, the city band plays in the bandstand. There have been weddings, class reunions, birthday parties, etc. You can bring wine or beer or food and enjoy the space.

Smokey Row

Nestled in the heart of Oskaloosa at 109 South Market Street, Smokey Row Coffee House has become a cherished community hub since its establishment. Our mission is to provide a welcoming space where locals and visitors alike can gather, relax, and enjoy quality food and beverages.Our menu boasts a diverse selection of offerings, including freshly brewed coffees, specialty drinks, and an array of breakfast items, salads, burgers, and sandwiches. We also feature an old-fashioned soda fountain and a variety of ice cream treats, catering to guests of all ages.The ambiance at Smokey Row is enriched by Oskaloosa memorabilia and live music events, all set within a historic atmosphere that reflects the town's rich heritage. We also offer a meeting room for community gatherings and private events, underscoring our commitment to being a true community gathering spot.At Smokey Row Coffee House, we take pride in our locally roasted coffees and our dedication to Midwest hospitality. Our vision has always been to create a space that enhances the lives of our employees and patrons, embodying the spirit of community and connection.We invite you to join us at Smokey Row in Oskaloosa, where good coffee and good people come together.

Oskaloosa City Hall

The Oskaloosa City Hall is a historic government building connected to the Oskaloosa Fire Department. The City Hall is a Renaissance Revival style architecture. It was originally designed along with the adjoining fire station in 1905 designed by Des Moines architect Frank E. Wetherell.

Oskaloosa Public Library

The library first opened in 1902 due to the Osky Women’s Club and a $20,000 Carnegie Foundation donation. The library has been in this same spot for 116 years! Like most libraries, it is more than a warehouse of books, and is more a technology driven information center. There was a major expansion and renovation in 1997. For over a year, the library moved to the west side of the square on the south corner while construction went on. When you look at the library, it is almost impossible to tell the old section from the new section. In a room on the second floor, there is a marble time capsule that was sealed on September 13, 2003. If you google ‘Oskaloosa library history’ you will find a list of what is buried in the capsule. The capsule will be opened on Friday, September 14, 2103, so put that on your calendar.

Shoemake-Muhl House

Penn Central Mall

Penn Central Mall opened its doors in 1985. A group of Oskalooa volunteers set out to replace deteriorated buildings in Oskaloosa's downtown. Penn Centeral Mall opened with a crowd of over 11,000 on hand. The group recognized a more comprehensive approach was needed to maintain the vitality of the community. They wanted to build on Oskaloosa’s base as a retail center for southeast Iowa and its position as a central traffic arealocated at the confluence of five highways.

Montage

Located in Penn Central Mall, the montage was built in 1985 by local artists Tom Stone and Marv Smith. The idea was to preserve pieces of Osky’s past while contributing to its future. It took a year to complete and cost $80,000. The montage was removed in 1998, returned to the mall in 2010, and revamped and unveiled in 2014. It is 80 feet long, 14 feet high and 6 feet deep. There are 356 articles, photos and artifacts in the montage. Marv Smith said “This was a little like building a ship in the middle of a desert. It’s hard to describe what you’re trying to do.” The montage is a reminder that Oskaloosa was built with a vision for the next 100 years and that the next 100 years belongs to us

Skate Park

The skate park, also known as Oskaloosa’s Urban Park was built in 2011 through Mah Comm Rec Foundation. It’s unusual because it has a kind of sculptural quality instead of basic metal ramps. There was some controversy about the location.The Oskaloosa Skatepark, located at 259 High Ave W, is an 11,000-square-foot concrete facility in the heart of downtown. Open daily from sunrise to 10 p.m., it features quarterpipes, rails, ledges, stairs, and more—designed for skateboards, BMX bikes, scooters, and in-line skates. The park blends functionality with urban style, including dynamic concrete patterns and granite accents. It’s free to the public and lit for evening use, making it a vibrant community hub for all skill levels.

Iowa Building

Stapp building

Iowa Masons Benevolent Society Building

Built-in 1876, the Iowa Masons Benevolent Society Building is an Italianate-style building influenced by the design of our town courthouse. The Iowa Masons Building houses a stove store, tinsmith, hardware, Iowa Masons Ben society, attorneys, and clothing store, and it is now Hawkeye real estate and Mahaska title.

Jaarsma Bakery

Jaarsma Bakery is located in Pella with an outlet store in Oskaloosa. The Jaarsma Bakery in Pella, Iowa, has been offering delicious "Dutch Treats" since 1898, when it was founded by Harmon Jaarsma who used recipes he brought with him as an immigrant from Holland. The business has been passed down for four generations and is now owned and operated by Harmon’s great-granddaughter Kristi and her husband. .Jaarsma is especially known for their Dutch Letters which Smokey Row sells and for making everything from scratch.

The Centennial Block

(Home town dental and HR block) Arch type—Italianate, built 1876 by Isaiah Frankel. The building is actually three storefronts with a bracketed cornice and central arched pediment. Between the three storefronts, the building has housed many different businesses over the years including a bank, insurance company, attorney offices, real estate, trunk and harness shop, drug store, clothing store, dry goods, billiards parlor, cigars, candy, department store, auto parts, fabric shop, and photography. Today it houses a dentist shop and H&R Block.

Mahaska County Courthouse