Downtown Osky Tour

Duration: Tour is 2-1/2 to 3 hours

Location: Downtown Oskaloosa

General Admission


Tours run rain, shine, or snow!

Get away from the hustle and bustle of large city food tours, and join us on an easy-paced walking tour of historic downtown Oskaloosa, Iowa

  • Try samples of delicious food from six restaurants
  • Learn interesting facts about Oskaloosa's architecture, history and culture
  • Meet new people
  • See beautiful historic buildings, sculptures, art, and more
  • Tours are small: between 2 and 15 people
  • Walking distance is approximately two miles with frequent stops

Restrooms at each stop

Handicap accessible restaurants

Total walking distance is under two miles

Vegetarian option available with prior notice

Tours run rain or shine!

Parking available on the town square or in the parking lots of the adjacent mall.

We recommend you bring a bottle of water with you.

What to Expect

Your tour guide will greet you at the Chief Mahaska statue on the west side of the town square directly across from Smokey Row coffee shop.

This is a walking tour that covers approximately 1-1/2 to 2 miles on flat, paved surfaces.

The tour ends at the same location as the starting point.


Where Will You Go?

Wood Iron Grille

Wood Iron Grille is owned and operated by Matt Gunn and Michael Glesener. Their vision is “making memories one plate at a time."

Hunter's Gift and Coffee Cafe

Frank and Shirley offer a small, quality menu with all homemade dishes. Besides the delicious food, Hunters has a impressive array of china, crystal, and other gift items

Grate Expectations

Kyle Brown is passionate about offering southeast Iowa “a fresh and unique dining experience focused on providing thoughtful food.”

The Book Vault

Since Grate Expectations is too far to walk, we will visit the Book Vault and experience two special places for one tasting!

The Brickhouse Cafe

The Brickhouse Cafe opened up in November 2017. Owner Kory Wright says “the time sure has flown by when you're having this much fun.” Kory is open for breakfast and lunch.

WanderLunch (weekdays only)

WanderLunch was started by Heather Nelson in 2019. Her vision for the restaurant was to have a small, carefully developed menu! And who doesn't love Grilled Cheese?

Smokey Row Coffee Shop

Smokey Row is THE place to meet in Osky! It's a gathering place for friends, business, politicians and more where you can enjoy coffee, ice cream, soups, sandwiches, and pastries.

Jaarsma Bakery

While at Smokey Row, you will get to try a treat from Jaarsma Bakery which has been offering delicious "Dutch Treats" since 1898!

Where to Meet

Street parking is available as well as public parking lots within one block of the starting and ending point. Starting and ending point is on the west side of the town square,108 South Market Street (Highway 63 South), Oskaloosa, IA., 52577, directly across from Smokey Row.

Get Directions

"Best way to get to know an area!"


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