This Quirky Iowa City With A Historic Downtown Holds A Long-Running Festival Art Lovers Adore

Iowa might conjure up images of farmland, considering the Hawkeye State is a major agricultural powerhouse, producing the most corn in the United States. However, in addition to having places like the Devonian Fossil Gorge with a 375-million-year-old ocean floor full of diverse fossils, Iowa also has a variety of vibrant places that are full of life and history. One of those cities is Oskaloosa, a small but lively city with a population of about 11,500 people. The city is named after Ouscaloosa, a Creek princess whose name translates in English to "last of the beautiful." It has become a great location for artists due to events like their annual Art on the Square festival as well as places like the Oskaloosa Art Center and Studios, which offers art education, sells art, and showcases exhibitions. 

Situated about 60 miles from Des Moines and 100 miles from Cedar Rapids, Oskaloosa is a quirky city due to its eclectic mix of activities available to visitors as well as its quaint small-town charm. The city has a historic downtown area, which, in 1986, was added to the National Register of Historic Places and officially labeled a local historic district. 

One of the features that makes the historic district so unforgettable is the architectural diversity on display, including buildings with commercial, Italianate, and Romanesque Revival designs. If you want to travel to Oskaloosa, then your best bet is to take a flight to Des Moines International Airport, which is about 60 miles away from the town.

One of Oskaloosa's most popular attractions is also Iowa's longest-running and most popular art festival, called Art on the Square. Each year in downtown Oskaloosa, the city's community gathers to celebrate the family-friendly festival that features artist vendors. Visitors don't have to be locals, as patrons nationwide are welcome. In 2018, Art on the Square celebrated its 50th anniversary, and since then, it's remained a popular event; in 2024, Art on the Square attracted over 3,000 attendees. 

Visitors can also expect to see live entertainment and chow down on a variety of unique dining options, as food vendors are often situated around the festival. What makes Art on the Square so special is that, not only is it a celebration of Oskaloosa's cultural landscape, but attendees can also purchase art from emerging artists as well as veteran ones. If you're looking for more sites to see in Oskaloosa, then City Square Park in the downtown area includes a historical monument, a bronze statue dedicated to Chief Mahaska, who was a 19th-century leader of the Iowa Tribe. He promoted peace and became a representation of his people's virtues.

Another worthwhile location for visitors is the Russell Wildlife Area, which was voted by Tripadvisor users as the number one "thing to do" in Oskaloosa. While the Hawkeye State is filled with wonderful options for scenic views and hiking, including the recreational trails in Spencer in Northwest Iowa, this particular county park is a sprawling 424 acres that contains five quarry ponds full of various kinds of fish, including bass, catfish, crappie, and bluegills. If you're wanting to hop on a canoe or kayak, then you're more than welcome, as those are permitted on each pond. There is also a nature trail for hiking that is about one mile in length and is perfect for birding and fishing. 

You can't go wrong eating out in Oskaloosa. For traditional American cuisine, your first stop should be Tasos Steakhouse (ranked number one on Tripadvisor), where fried pickles, buckets of chicken, house ribeye, and jumbo shrimp are just some of the dishes you might find yourself digging into. If you visit Oskaloosa and don't go to Julie's Homestyle Cafe, you have missed out on a local staple. The cafe is a favorite for locals, serving up homestyle dishes like sausage gravy on biscuits, breaded tenderloin, cinnamon rolls, and various kinds of pie. Open since 2009, the cafe provides a small-town atmosphere, and reviewers on Yelp write that it is a "must" spot to visit. 

If you're craving wine and can't make it to Iowa's best wine destination of Dubuque, then you should head over to Tassel Ridge Winery. This particular winery and vineyard is renowned, having won the Gold Prize in the 2023 American FineWine Rosé Competition. In addition to offering dry, semi-sweet, sweet, fruit-based, and dessert wines, they also offer an all-day menu of food that includes salads and freshly baked bread.

If you'd like to stay the night in Oskaloosa, then the Fairfield Inn & Suites by Marriott Oskaloosa (ranked number one on Booking.com) is a solid choice. The hotel has a variety of rooms and suites and provides amenities like free breakfast, an indoor pool, and a fitness center. But if you're willing to travel a little further, then heading to Hotel Grinnell, about 35 miles away in the town of Grinnell, will have you staying in upscale rooms and suites. The award-winning hotel even offers a penthouse suite, which includes a canopy bed and personal salon.