Oskaloosa, Iowa, though perhaps overshadowed by the state's agricultural prominence, emerges as a captivating destination rich in history and cultural vitality. This lively city of roughly 11,500 residents, named after the Creek princess Ouscaloosa, meaning \"last of the beautiful,\" offers a distinctive blend of small-town allure and vibrant artistic expression. Its historic downtown, designated a local historic district in 1986 and listed on the National Register of Historic Places, showcases an impressive array of architectural styles, from commercial to Italianate and Romanesque Revival designs. The city's commitment to the arts is evident through institutions like the Oskaloosa Art Center and Studios and, most notably, the long-running \"Art on the Square\" festival, making it an unexpected cultural hub in the heart of the Hawkeye State.

Situated about 60 miles from Des Moines and 100 miles from Cedar Rapids, Oskaloosa provides a charming retreat. The city's most celebrated event is undoubtedly \"Art on the Square,\" Iowa's longest-standing and most popular art festival. This annual gathering transforms downtown Oskaloosa into a lively marketplace, drawing over 3,000 attendees in 2024 and celebrating its 50th anniversary in 2018. The festival not only provides a platform for both emerging and established artists to display and sell their creations but also features live entertainment and diverse food vendors, creating a festive atmosphere for visitors of all ages.

Beyond the artistic endeavors, Oskaloosa offers additional points of interest for visitors. City Square Park in the downtown area hosts a significant bronze statue dedicated to Chief Mahaska, a 19th-century leader of the Iowa Tribe, revered for his peaceful advocacy and embodying his people's virtues. For nature enthusiasts, the Russell Wildlife Area stands out as a top attraction, according to Tripadvisor users. This expansive 424-acre county park features five quarry ponds, ideal for fishing various species like bass, catfish, and bluegills, and also permits canoeing and kayaking. A mile-long nature trail offers excellent opportunities for birdwatching and hiking, further enhancing Oskaloosa's appeal as a multifaceted travel destination.

When it comes to culinary delights, Oskaloosa presents a range of enticing options. For classic American fare, Tasos Steakhouse is a highly-rated choice, known for its hearty dishes such as fried pickles and ribeye. Another local favorite, Julie's Homestyle Cafe, has been serving up comforting, traditional dishes like sausage gravy and cinnamon rolls since 2009, creating a welcoming, small-town dining experience. Wine aficionados can explore Tassel Ridge Winery, an award-winning establishment recognized for its diverse selection of wines, from dry to sweet and fruit-based, complemented by an all-day menu. For overnight stays, the Fairfield Inn & Suites by Marriott Oskaloosa offers comfortable accommodations with amenities like an indoor pool and complimentary breakfast. Alternatively, the upscale Hotel Grinnell, located about 35 miles away, provides a luxurious option with its award-winning rooms and suites, including an exclusive penthouse suite.