Oskaloosa’s town-square holiday lights will be switched on Nov. 21, 2026, as the city’s Painting with Lights display begins another season. The display’s documented history reaches back to 2016: KCCI reported that the lights were first turned on that year. That establishes a decade between the first lighting and this year’s event, though it does not by itself show whether the display operated every year.
The setting has a longer civic history. The City of Oskaloosa says the City Square Commercial Historic District was added to the National Register of Historic Places and designated a local historic district in 1986. Oskaloosa Main Street, which is part of the Mahaska Chamber & Development Group, also dates the community’s Main Street designation to 1986. Those records place the light display in a square recognized both as a historic district and as the center of a longstanding downtown program.
What visitors can expect
According to Oskaloosa News, the Oskaloosa City Band is scheduled to play at 5 p.m., with Citizen of the Year Linda Fox set to switch on the square’s lights at 6 p.m. The free evening includes cookies, hot cocoa and popcorn, photo opportunities with Santa, and free horse-drawn wagon rides offered by Mahaska Drug. Food trucks are expected on the east side of the square from 5 to 8 p.m.
The same report says a raffle will follow the lighting ceremony, with 20 prizes and proceeds supporting installation and maintenance. Tickets are available at Mahaska Drug and the Mahaska Chamber & Development Group through Nov. 17. Oskaloosa News reports that the lights are scheduled to shine nightly from 4:45 to 11 p.m. through Jan. 10, 2027.
A project built around the square
The Mahaska Chamber & Development Group says the display uses more than 300,000 LED lights on buildings around all four sides of the square. Its description of Painting with Lights notes that installation takes several weeks and depends on community volunteer work and donations. The scale of the display therefore rests not just on the event night, but on work completed before the season begins and support that helps keep it operating.
