If you’re looking for some of the best Christmas lights in Iowa, you have to plan a trip to Oskaloosa, Iowa. Located about 20 minutes southeast of Pella, this cute town deserves a spot on your Iowa Travel Bucket List!

We visited Oskaloosa, Iowa in partnership with the Mahaska Chamber and Development Group, but all opinions are mine.

Brief History of Oskaloosa

Oskaloosa, referred to as Osky by its inhabitants, was first platted in 1844 after a group of Quakers settled in the area. The town was named for a Creek princess named Ouscaloosa, who was forced to marry the Seminole Chief Osceola. According to town lore Ouscaloosa means “last of the beautiful.” And the name fits the town very well!

Mahaska County, Iowa

Mahaska County itself was named after a chief of the Ioway tribe, Chief Mahaska or White Cloud. Interestingly, there is also a town named Mahaska in Kansas. 

As the county seat of Mahaska County in Iowa, Oskaloosa has a beautiful downtown City Square Park and county courthouse. During the holiday season, the entire square transforms with over 250,000 LED hanging lights and the town is known for its beautiful lights and annual lighted Christmas Parade! 

Go for the lights, but stay for all other fun things to do in Oskaloosa and Mahaska County, Iowa! There are quite a few things your family will enjoy in this lovely Iowa town!

Fun Things to Do in Oskaloosa and Mahaska County Iowa

Take in the Painting with Lights Display

Easily THE most impressive light display I have ever seen, you must make a trip to Oskaloosa during the holidays to see what how the town decorates its square. Every single building is covered in lights, including the Mahaska County Courthouse. New this year is the gorgeous rainbow tree we all loved!

The lights are illuminated from November 22 to January 8, 4:30 pm – 11 pm each day.

Watch the Lighted Christmas Parade

An Osky staple for over 30 years, the annual Lighted Christmas Parade is generally held the weekend after Thanksgiving. It was voted THE NUMBER 1 holiday event by Main Street Iowa and it is really spectacular!

The parade starts at 7 pm and don’t be late, because thousands of people line the Oskaloosa Square waiting for the numerous lighted floats to start. Make sure to dress warmly and bring candy bags for the kids! The parade lasts over an hour. Some of the floats have been used for years and they are all beautiful.

Tour the Annual Holiday Tour of Homes

Oskaloosa’s annual Tour of Homes is held the same weekend as the Lighted Christmas Parade. Proceeds from the tour benefit Sieda Community Action, an outreach program that helps people in need people, through advocacy, counseling, education, partnerships, and supportive services. This year four different homes opened their doors to the public.

It’s always fun to peek into other people’s lives and see how different folks decorate for the holiday! 

Visit the Mahaska County Freedom Rock

Oskaloosa is home to the Mahaska County Freedom Rock – Iowa’s 39th Freedom Rock. If you aren’t familiar with Freedom Rocks, Iowa artist and state legislator, Ray “Bubba” Sorenson II, was commissioned to paint large boulders for all of Iowa’s 99 counties. Each county’s Freedom Rock is a large multi-ton boulder painted with a mural to honor the county’s military history. 

The last Freedom Rock will be dedicated in 2022 at the Linn County Fair. It has taken eight years to finish all 99 Freedom Rocks. Muscatine County’s Freedom Rock is housed in my town of Wilton. We saw the Webster County Freedom Rock when we visited Fort Dodge and we saw the Keokuk County Freedom Rock in What Cheer when we drove home from Oskaloosa! 

Mahaska County Freedom Rock | 2348 Hwy. 92 E., Oskaloosa

Throw Axes at Axe-Club Oskaloosa

If axe throwing is your thing, you’ll definitely want to throw some axes at Osky Axe-Club! Located in Penn Central Mall, this axe-club is part of the Old School Pinball Arcade. They have axe-throwing packages for everyone! If axe throwing isn’t your thing, check out the Old School Pinball Arcade just across from the Axe-Club!

Penn Central Mall | 200 High Avenue West, Oskaloosa

Enjoy Coffee and Soup at Smokey Row

We really enjoyed morning coffee at Smokey Row. Not only do they serve fantastic cup of joe, the kids loved their smoothies and hot chocolate too. Smokey Row is a really neat stop in Oskaloosa! 

They have free book tables, games, swag for sale, and what promises to be a delicious bowl of soup! Another item on my must go back and try list: Cheeseburger Chowder!

Smokey Row Oskaloosa | 109 S Market Street Oskaloosa 

Find the Murals

If you’re a fan of murals, Oskaloosa has several to find! They’re conveniently located around the square so you don’t have to hunt hard to find them all! Our kids tried to climb aboard the trolley, pictured above.

Learn more about them at them Mahaska Chamber and Development Group.

Tour the Alley in Oskaloosa, Iowa

Located on Market Street between Smokey Row and , the Alley is a fun place to learn about the history of Oskaloosa, take in music and arts events, and dine al fresco in warmer weather.

Enjoy Iowa’s 2019 Best Burger at Wood Iron Grille

Located on Oskaloosa’s Public Golf Course, Wood Iron Grille is home to Iowa’s Best Burger of 2019! Trying “the best of” is always a good excuse to go out for a meal, right?

Wood Iron Grille | 2214 South 11th Street, Oskaloosa 

Visit the Book Vault and other Independently Owned Stores around the Square

If you like independent bookstores, you’ll definitely need to stop in at the Book Vault in Oskaloosa! Located right next to Smokey Row, the Book Vault is so much more than a bookstore! Unfortunately, we arrived after they closed, but this store is definitely on my must-do list next time we’re in Oskaloosa. A few other independent stores you’ll want to check out in Oskaloosa include Betsey’s Boutique Shop, Brown’s Shoe Fit, and Mahaska Drug.

Book Vault | 105 South Market, Oskaloosa

Wine Tasting at Tassel Ridge

For $15 a person, enjoy seated wine tastings at Tassel Ridge Winery, the largest winery in Iowa. The $15 fee gets you a flight of wine, your choice of red, white, or rosé, plus a small loaf of freshly baked bread, gouda cheese from Frisian Farms, and Tassel Ridge dipping sauce! We had a lot of wine during our seated wine tasting experience! 

Call for reservations!

Tassel Ridge Winery | Leighton, IA |  641.672.9463

Junking at North Creek Antiques

We were excited to stop in at North Creek Antiques on the way to Oskaloosa from Pella. You can find just about anything in the two big red sheds including home decor, furniture, items salvaged from old barns and homesteads! If you like picking through lots of nostalgic items, a stop at North Creek Antiques needs to be on your short list!

North Creek Antiques | 1245 IA-163 Pella, Iowa 50219

Where to Stay in Oskaloosa, Iowa

Oskaloosa has several accommodation options. We stayed in the new Fairfield Inn and it was lovely. Conveniently located close to downtown Oskaloosa, it was clean and comfortable. The kids loved the pool and the breakfast selections. They especially loved the waffles with chocolate chips and whipped cream! What a treat!

Here’s a link to make reservations for hotels in Oskaloosa.

Download the Mahaska County Visitor’s Guide and plan your trip to Oskaloosa, Iowa!

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