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Holiday Events

Christmas Events and Holiday Festivities in downtown Oskaloosa

Holiday Event Information

"Christmas isn't a day. It's a frame of mind." That famous line from the classic Miracle on 34th Street sums up the holiday season here in Oskaloosa—and builds on the theme of our 34th Annual Lighted Christmas Parade: "Miracle on Market Street." 

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2021 Holiday Events Brochure

Download the 2021 Holiday Events Brochure, which contains:

Painting with Lights

November 20, 2021 through January 8, 2022 • Downtown Oskaloosa

Lights! Camera! Christmas! Come for the shops. Stay for the photo ops. Experience Oskaloosa's dazzling downtown! Each day, more than 250,000 LED lights illuminate the fronts of buildings surrounding the historic City Square Park. The lights turn on for the season on November 20 at 6 pm, and will then glow each day from 4:30 pm to 11:00 pm through January 8. 


Young Ambassador Ceremony

Monday, November 29, 2021 • 6 PM • Penn Central Mall, Center Court

There’s no better way to start Parade Week than to crown Oskaloosa Main Street’s Young Ambassadors! Join us in Center Court in Penn Central Mall for the announcement of our King and Queen. All participants will receive prizes and enjoy a special storytime. Vote for your favorite candidates now through 8 AM, Monday, Nov. 29! View the list of participating children and where to vote. 

Check out the Young Ambassador Ceremony on Facebook. 


Merry Little Downtown Christmas

Friday, Dec. 3 • 5:30 PM - 7:30 PM • City Square Park 

Bundle up and make your way to historic downtown Oskaloosa for fa-la-la-la fun on the Friday night before the parade!

• Warm up with hot cider and cocoa with cookies.

• Meet Santa, Mrs. Claus, and their reindeer.

• Go on a horse-drawn wagon ride around City Square Park beneath the glow of Painting with Lights! Freewill donation. (Donations go toward continuing Painting with Lights.)

Check out Merry Little Downtown Christmas on Facebook


Lighted Christmas Parade

Saturday, Dec. 4 • 7:00 PM - 9:00 PM • Downtown Oskaloosa 

Experience Iowa's #1 Holiday Event, featuring 60+ lighted parade entries under the spectacular glow of Painting with Lights.

Theme: "Miracle on Market Street" 

4:00 - 6:00 PM • Horse-drawn wagon rides around the Square. $5/person. (Proceeds support continuing Painting with Lights.) Place your bid for a chance to ride in the horse-drawn wagon during the parade!

7:00 PM • Parade begins! 

Check out the Lighted Christmas Parade on Facebook. 

View the 2021 Parade Map in a new window. 

Christmas Story Window Walk

Saturday, Dec. 11 & Saturday, Dec. 18 • 3:00 PM - 5 PM • Downtown Oskaloosa

Gather your family and walk around downtown Oskaloosa to read 'Twas the Night Before Christmas on 15 posters illustrated by local artists—all displayed in decorated windows of Main Street businesses.

On Saturday, December 11 and Saturday, December 18, from 3 pm to 5 pm, check in at the welcome table inside Penn Central Mall (near Pizza Ranch) to get a map, goodie bag, and special edition coloring book featuring all the locally-illustrated posters. When you've completed the window story walk, return to the welcome table in the mall to vote for your favorite and enter to win a prize!

The posters will be on display during the month of December for self-guided window story walks.

The Christmas Story Window Walk is brought to you by the Golden Goose Club and Oskaloosa Main Street, thanks to grant funding from the Mahaska County Community Foundation.

Check out the Christmas Story Window Walk on Facebook. 


Holiday Luncheon

Friday, Dec. 17 • 11:30 AM - 1:00 PM • Debbie's Celebration Barn

Start planning your "Miracle on Market Street/ Miracle on 34th Street"-inspired attire! Oskaloosa Main Street's Holiday Luncheon is back for 2021!

Tickets are $20/each and are available for purchase at Mahaska Chamber (222 1st Ave E). 

Check out the Holiday Luncheon on Facebook. 


Past Events


Turn on the Lights!

Saturday, Nov. 20 • 5:30 PM - 8 PM • City Square Park 

Oskaloosa Main Street is kicking off the holiday season by turning on Painting with Lights and our new 20-foot twinkling tree!

5:30 PM • Enjoy hot cocoa, cookies, warm apple cider. Meet Santa, Mrs. Claus, and their reindeer. Enjoy live music played by City Band volunteers. 

6:00 PM • A special guest will flip the switch to turn on Painting with Lights and light the tree!

6:00 - 8:00 PM • Horse-drawn wagon rides around the Square. Freewill donation. (All donations go toward continuing Painting with Lights.) 

Check out Turn on the Lights! on Facebook. 

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