Located just an hour southeast of Des Moines, Oskaloosa boasts big city fun with a small-town feel. The community’s historic town square invites visitors to explore its shops, restaurants and artwork while outdoor recreation opportunities are woven throughout town and beyond its borders. No self-exploration needed – this itinerary tells you exactly where to go and what to do.
Day 1
Do: Downtown Shopping
Start your adventure in downtown Oskaloosa, where the historic town square is lined with locally owned shops and boutiques. Browse antiques, gifts, books, coffee, and décor while admiring seasonal flower planters and more than a dozen public art pieces, including colorful murals. On Thursday nights in the summer, the square comes alive with Thankful Thursday in the Alley and free concerts from the Oskaloosa Municipal Band at the 1912 bandstand.
Do: Oskaloosa Activities
Take a break at the Oskaloosa Art Center for local exhibits and creative workshops, then add some fun to your afternoon with Old School Pinball & Arcade or axe throwing at Oskaloosa Axe Club. If you need to unwind, go for a tasting at Rosso & Wine.
Eat: Bridget’s Public House or The P.O. Box
When dinner rolls around, choose from two lively downtown options. Bridget’s Public House blends Irish hospitality with American classics in a cozy pub setting, while The P.O. Box serves gourmet burgers, sandwiches, and pub fare inside Oskaloosa’s historic 1904 post office building.
Stay: McNeill Stone Mansion B&B
After a day of exploring, check in at the McNeill Stone Mansion B&B, a stunning historic mansion that offers unique overnight stays filled with charm, architecture, and modern comforts.
Day 2
Eat: Spirit Café
Stop for brunch at Spirit Cafe, where Oskaloosa Schools students with special needs and peer mentors prepare homemade brunch and lunch favorites while gaining real-world job skills. The cafe is a hub for community connection and inclusivity, making it a dining experience with meaning.
Do: Mahaska County Environmental Learning Center
Begin the day at the Mahaska County Environmental Learning Center in Caldwell Park. Inside, explore live animal exhibits, hands-on displays, and a life-size mammoth replica skeleton. Outside, discover trails and the brand-new Nature Playscape featuring natural climbing structures and a mammoth play sculpture.
Eat: TRIO Entertainment
In the afternoon, make your way to TRIO Entertainment, a new complex offering a true one-stop destination for fun plus a full bar and menu featuring Oskaloosa’s best boneless wings and smash burgers, plus bowls, salads, handhelds and flatbreads. While you’re there, be sure to test your skills on the golf simulators and pickleball and tennis courts or enjoy movies and live entertainment.
Do: Mahaska County Recreational Trail
Head out to the Mahaska County Recreation Trail, a nearly 15-mile loop perfect for biking and walking in warmer months or cross-country skiing and snowshoeing in winter. Along the way, discover the Solar System Model, planetary markers placed to scale, along the trail.
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