Oskaloosa is full of cheer this time of year.

And why shouldn’t we be? The snow-coated streets, decorated homes, and air filled with notes of Bing Crosby all signal a joyous season for celebration. 

Thankfully, the community of Oskaloosa is organizing an abundance of holiday events for everyone’s participation. 

While there are too many to list them all here, we’ve centralized some of the key events to pencil in your December calendar. 

‘Tis the Season! 


Visit Santa Claus

Penn Central Mall — November 29 – December 22

Ol’ Saint Nick has decided to graciously gift the people of Oskaloosa with his presence throughout the weekends of December. 

From November 29 – December 22, Penn Central Mall will host Santa every Friday – Sunday from 12pm – 2pm, and Thursday nights from 6pm – 8pm. 

Stop by the mall on any of these dates to snag a few timeless photos with the man in the red suit.


Holiday Happenings 

Penn Central Mall — November 30

To help kick off the holiday season, Penn Central Mall is holding a number of events on Saturday, November 30. 

The Holiday Craft & Vendor Show begins at 10am and marks a perfect occassion to take on your holiday shopping. Plus — being November 30 is “Small Business Saturday” — there’s no better time to support local business.

Amidst the shopping thrills, the Holly Jolly Family Fest is being hosted by VFW Post 2237 and the VFW Auxiliary, and includes crafts, games for all ages, prizes, and more. This free event will take place from 11am – 2pm. 

And, of course, Santa awaits your greeting anytime from 12pm – 2pm. 


Main Street Lighted Christmas Parade

Downtown Oskaloosa — December 7

Oskaloosa’s 32nd Annual Lighted Christmas Parade is one of Oskaloosa’s longest-standing traditions.

Around 60 floats will march down Main Street starting at 7pm, while their lights illuminate Downtown Oskaloosa. 

Other events are held throughout the week leading up to the parade, as well — including the Holiday Market, Festival of Trees, and more. 

Visit the official festival page for more information. 


Merry Little Downtown Christmas

Main Street — December 14

There’s no better place to gather and celebrate the holidays than the center of the city. 

Downtown Oskaloosa is hosting a night of festivities on Saturday, December 14 from 5pm – 8pm. Santa will settle down at City Square Park for visitors to greet, while free horse-drawn wagon rides take bundled-up families around the brilliantly decorated downtown. 

More activities and events are sure to occur, so check out the official page for updates on the event. 


Community-Wide Caroling

Penn Central Mall — December 18

Nothing beats the cheer of Christmas caroling. 

On December 18, Oskaloosa residents will meet at Penn Central Mall, sing some songs, enjoy a few holiday refreshments, and head out to carol around town. 

All voices are welcome!


As we mentioned earlier, there are many other holiday events around Oskaloosa in December. These are simply some of the highlights. 

To see a more complete list, visit the Oskaloosa Chamber’s events page.  

From all of us at the EverSpring Inn & Suites, we wish everyone a Merry Christmas and a Happy New Year!