Painting with Lights in Oskaloosa (2026)

Oskaloosa doesn’t stop at hanging Christmas lights along the rooflines. During Painting with Lights, more than 300,000 LED Christmas lights cover the fronts of buildings surrounding City Square Park, turning all four sides of the downtown square into a holiday attraction.

Add Christmas music playing through outdoor speakers and a walk around the historic square, and you have a good reason to plan an evening road trip.

When can you see the lights in 2026?

The season begins Saturday, November 21, 2026, with Oskaloosa’s Turn on the Lights celebration. Activities run from 5 to 8 p.m., with the lights switched on at 6 p.m.

For regular nightly viewing, the Mahaska Chamber lists the display’s hours as 4:45 to 11 p.m., continuing through early January. Opening night follows its own schedule, with the ceremonial lighting at 6 p.m.

What happens at the opening celebration?

If you want more than an evening walk to see the lights, November 21 is the night to visit.

The published 2026 schedule includes horse-drawn wagon rides from 5 to 8 p.m., an Oskaloosa City Band performance from 5:30 to 6 p.m., and the lighting ceremony and raffle drawing at 6 p.m.

Santa, reindeer, food trucks, and holiday refreshments are also advertised. There is no admission charge for the opening event.

These activities are part of the kickoff celebration. Wagon rides and Santa visits are not advertised as nightly offerings.

Location: City Square Park and the surrounding downtown storefronts in Oskaloosa, Iowa. The opening celebration is listed at 208 First Avenue East.

Check the Mahaska Chamber’s holiday events page before traveling for the latest updates.

Walk the square and enjoy the view

The lights cover buildings on all four sides of the square, so give yourself time to explore on foot.

Include a stop at the historic bandstand in City Square Park. The Mahaska Chamber recommends climbing its stairs for a 360-degree view of the illuminated buildings. Christmas music playing around the square adds to the atmosphere.

My suggestion: arrive before dark, explore downtown, and stay as the evening settles in. You’ll have time to enjoy the storefronts before seeing the square in its holiday colors.

A community effort behind the lights

Painting with Lights takes more than an afternoon of decorating. According to the Mahaska Chamber, installation takes several weeks, while planning and fundraising happen throughout the year.

Donations from businesses and individuals, along with volunteer work, help make the display possible.

Make it a downtown Oskaloosa outing

Build in time for shopping, coffee, or dinner before viewing the lights. Downtown offers restaurants, cafes, boutiques, and Book Vault, a bookstore inside a renovated historic bank building. Check individual business hours when planning your visit.

Pair your visit with the lighted Christmas parade

For another festive night to visit, mark Saturday, December 5, 2026. Oskaloosa’s 39th Annual Lighted Christmas Parade begins downtown at 7 p.m.

It’s an opportunity to enjoy both the illuminated square and the parade during the same trip. Check the Mahaska Chamber’s calendar closer to the date for updated parade routes and parking details.

All photos by Brian Abeling / Iowa Road Trip