Oskaloosa Main Street Seeking Young Ambassadors for Holiday Season; Entry Deadline October 23rd

OSKALOOSA, Iowa — Oskaloosa Main Street is accepting entries for its annual Young Ambassadors Contest, giving area children an opportunity to represent the community during this year’s Christmas celebrations.

The contest is open to children ages three through kindergarten. The contest will select one boy and one girl as Oskaloosa’s Young Ambassadors, with winners announced at a ceremony on Monday, November 30th, at 6 p.m. at Penn Central Mall.

Unlike a traditional contest judged on appearance or talent, the community selects the Young Ambassadors through a fundraising competition.

Each registered child will have a secure voting canister placed at a participating local business. Community members can support their favorite contestants by placing money in the canisters.

The boy and girl who collect the most money in their respective canisters will be named this year’s Young Ambassadors.

Voting begins Monday, November 2nd, and continues through the morning of Monday, November 30th.

Families may request a preferred business location for their child’s voting canister, but they must first obtain that business’s permission.

Money raised through the contest will benefit a local preschool and help cover expenses associated with Oskaloosa’s annual Lighted Christmas Parade.

Registration Deadline Approaching

Parents or guardians who want to enter their children must submit an application by 4 p.m. on Friday, October 23rd.

The registration fee is $5 per child, and each entry must include a photograph no larger than 3-by-5 inches.

Applications must also include the child’s name, birthdate, parent’s name, address, phone number, school, favorite activity, and what the child wants for Christmas.

Submit completed entries to Oskaloosa Main Street at 222 First Avenue East in Oskaloosa, on the second floor of Nicolet National Bank.

Applications are also available on the Mahaska Chamber & Development Group website at https://www.mahaskachamber.org/page/main_street_holiday_events/.

Contestants Invited to Participate in Christmas Parade

All contestants will be recognized during the November 30th ceremony at Penn Central Mall, when the two Young Ambassadors will be announced.

The contest also gives children the chance to take part in another Oskaloosa holiday tradition.

Every contestant, whether or not they are selected as a Young Ambassador, will have the opportunity to participate in the annual Lighted Christmas Parade on Saturday, December 5th, at 7 p.m.

This year’s parade theme is “Winter Wonderland: Let It Glow,” with lighted floats and holiday displays planned for downtown Oskaloosa.

Oskaloosa Main Street organizes the Young Ambassadors Contest as part of the community’s annual holiday activities.

For additional information, families can contact the Mahaska Chamber & Development Group at 641-672-2591.

Posted by on Oct 9 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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