Oskaloosa Main Street Announces Holiday Events, Christmas Lighting and 39th Annual Parade

Oskaloosa Main Street Director Angie Foster stopped by the Oskaloosa News studio to talk about the upcoming holiday events.

Oskaloosa Main Street Director Angie Foster stopped by the Oskaloosa News studio to talk about the upcoming holiday events.

OSKALOOSA, Iowa – Oskaloosa’s downtown Christmas lights will be turned on November 21st, kicking off several weeks of holiday activities. These include the 39th Annual Lighted Christmas Parade on December 5th.

Oskaloosa Main Street has announced a full schedule of holiday events, such as the Young Ambassador ceremony, home and business decorating contests, and a holiday luncheon. Main Street Director Angie Foster recently spoke with Oskaloosa News about the upcoming celebrations, ways residents can get involved, and the fundraising needed to keep the downtown Christmas lights shining each year.

Holiday Lights Return November 21st

The season starts Saturday, November 21st, with Turn on the Lights at Oskaloosa City Square Park. Activities run from 5 to 8 p.m. and include free horse-drawn wagon rides, a visit from Santa, reindeer, and refreshments like cookies, hot chocolate, cider, and popcorn.

The Oskaloosa City Band will perform from 5:30 to 6 p.m. Linda Fox, this year’s Citizen of the Year, will help turn on the downtown Christmas lights around 6 p.m. Foster said the countdown and lighting will happen between 6 and 6:15 p.m.

This event brings back Painting with Lights, the holiday display that lights up buildings around the square. Admission is free.

Raffle Helps Pay for the Lights

Keeping the downtown display running takes more than just turning on a few bulbs. Foster said organizers need to raise about $35,000 each year to pay for installation, removal, repairs, replacement lights, and storage.

The Painting with Lights raffle features 20 prize packages, each valued between $200 and $500. Prizes include gift cards from local businesses and a family or parent-and-child photo session.

Tickets are $10 each or five for $40 and are available through November 17th at the Mahaska Chamber & Development Group office, 222 First Avenue East. Winners will be drawn during the November 21st celebration and do not need to be present.

Young Ambassadors and Holiday Decorations

Another tradition is the Young Ambassador ceremony, set for Monday, November 30th, at 6 p.m. in Penn Central Mall.

Children ages 3 to 5 can join the contest. Supporters donate money in voting containers at participating businesses, and a young boy and girl are chosen as ambassadors. All contestants can take part in the Christmas parade. This year’s donations will help SIEDA Head Start in Oskaloosa and support holiday festivities.

Homes and downtown businesses will also brighten the season with decorating contests.

The home contest features awards like Best of Show, the Griswolds Award, Most Festive, Best Use of Lights, and Best Use of Color. Winners get Chamber Cash, and organizers plan to share a map of participating homes so residents can tour the displays.

Residents who want to enter the home contest can contact Lori Oaks at 641-660-7011. Downtown stores will also compete by decorating their holiday windows.

Lighted Christmas Parade December 5th

The main event is Oskaloosa’s 39th Annual Lighted Christmas Parade, set for Saturday, December 5th, at 7 p.m. downtown.

This year’s theme is “Winter Wonderland: Let It Glow.”

Businesses, organizations, families, and other groups are welcome to enter decorated floats or other lighted displays. Parade applications are available through the Mahaska Chamber. Anyone interested in entering should contact the office for the latest submission details.

Foster said last year’s parade had nearly 70 entries. Organizers are already planning for the parade’s 40th anniversary in 2027.

Downtown restaurants and shops will welcome visitors on parade day. Horse-drawn wagon rides are also planned before the parade, with a fee of about $5 for each ride.

The parade usually lasts about an hour to an hour and a half.

Holiday Luncheon and Volunteers

A holiday women’s luncheon is set for Friday, December 11th, from 11 a.m. to about 1:30 p.m. at W Celebration Barn.

Foster said the ticketed event will include door prizes and a chance to make an ornament to take home. Anyone interested in tickets can contact the Chamber.

Foster also highlighted the need for volunteers. The five-person office manages Main Street, Chamber activities, tourism, the visitor center, and economic development. Community volunteers make these events possible.

For event details, applications, or volunteer opportunities, visit www.mahaskachamber.org or call 641-672-2591. The Chamber’s online calendar also lists more holiday activities happening in the community.

Posted by on Nov 1 2026. Filed under Local News. You can follow any responses to this entry through the RSS 2.0. Both comments and pings are currently closed.

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