Main Street Monthly News
This e-newsletter will be sent monthly to inform you about all things Oskaloosa Main Street!

In this issue:

  • Main Street Director Message
  • Upcoming Events
  • Sweet Deals
  • Things on the Horizon...
Main Street Director Message

The Oskaloosa Main Street Board will be conducting a strategic planning session with Michael Wagler from Main Street Iowa.  We want to know about your needs, our strengths/areas of improvement, and our community events.  All Main Street District business/building owner contacts should have received an email with a link to a brief survey.  If you have not yet completed the survey, please do so by November 1.  If you did not receive the link and are a downtown Main Street district business and/or building owner, please contact Amy at  Your input is valued and will help us determine our plans for the future.

Upcoming Main Street Events

Our Halloween Window Art StoryWalk® opens tomorrow

(Saturday, October 15). The featured story is, Mr. Pumpkin's Tea Party by Erin Barker. Eighteen downtown business windows are beautifully painted with fall scenes, including book illustrations. 

The StoryWalk® starts at Town Square Dental Care and ends at Mobile Device Repair. A list & map of all locations can be found in the window at Town Square Dental Care - snap a pic and have a great time reading the fun story and seeing the amazing art by talented locals. If you take any photos along the way, be sure to tag Oskaloosa Main Street and use #HalloweenWindowWalk.

Free make'n'take activities, coloring, glow-in-the-dark tattoos, snacks, photo backdrop, and games will be offered at our Downtown Tea Party on Saturday, October 29 from 10 AM-2 PM in the south hall of the Penn Central Mall. This event is come & go as you please. Costumes are not required but are welcome. To prep for the holiday season, a canned food drive will be held during our Downtown Tea Party. Non-perishable food donations will be delivered to the Ecumenical Food Cupboard after the event.  VOLUNTEERS are needed for the Downtown Tea Party, anyone 13+ can help:

The Trick-or-Treat Parade will not take place this year. We are encouraging families to take part in the Window Art StoryWalk® and other local Halloween events instead. 

Full details about the Window Art StoryWalk® can be found on our website at and Oskaloosa Main Street Facebook page.

Sweet Deals for Main Street Businesses

Main Street's Economic Vitality Committee presented

MidWestOne Bank with a Sweet Deal for 139 years in business

and 36 years in the Main Street District.

Things on the horizon...


Holiday Happenings in

Downtown Oskaloosa!

Turn on the Lights

Saturday, November 19 5:00-8:00 PM

Downtown Oskaloosa's Painting with Lights will officially be turned on for the holiday season.

Young Ambassadors Contest

Monday, November 28 6:00-7:00 PM

Children must enter this contest by October 21. Voting canisters will be placed in local businesses & voting will take place October 31-November 28. Children will be recognized at the contest on November 28.

Home Decorating Contest

Entry deadline is noon on Monday, November 28.  Entries will be judged the week of the Christmas Parade.

Window Decorating Contest

Entries are due by November 9. 

We would like to have all windows decorated by November 19 for Turn on the Lights visitors to see.  Entries will be judged the week of the Christmas Parade.

Merry Little Downtown Christmas

Friday, December 2 5:30-7:30 PM

Celebrate the season with a visit to downtown Oskaloosa to see Santa, take photos around our dazzling downtown, and go for a ride in a horse-drawn carriage.

Lighted Christmas Parade

Saturday, December 3 7:00 PM

Continue the celebration with the 35th Annual Lighted Christmas Parade in downtown Oskaloosa. Bundle up and enjoy the sights and sounds!

Holiday Luncheon

Friday, December 16 

11:30 AM-1:00 PM

*Tickets Required* Festive luncheon featuring delightful food, cheery entertainment, and awesome door prizes. Purchase tickets in advance for $20 at the Mahaska Chamber Office.


If you are interested in serving on any of the Holiday Events Committees or volunteering at any of these events, please contact Amy at or 641-672-2591.

THANK YOU to those who attended our first-ever ELEVATE: Upper Story Housing Tour on October 1! We appreciate your support and hope you had a great time seeing all of the spaces on the tour. 

A special thank you to all of the building/business owners who offered their spaces for the tour, volunteers who helped the event run smoothly, and the committees who put lots of time into planning the event! Since the event was so successful, we plan to have another tour in 2023!

If you attended ELEVATE and have not already taken the survey, please provide us with your feedback at

  • Painting with Lights has started going up.  Thank you for your support of this beautiful tourist attraction and for your patience as the lights go up. Lights will be turned on at 6:00 p.m. on Saturday, November 19.

Calling All Photographers -

We need your help!

The Painting with Lights Committee is looking for photographers for Christmas mini sessions in downtown Oskaloosa as a fundraiser for Painting with Lights.  

We would like to give local photographers the opportunity to be present at one or more of our events this holiday season.

What would this include?

  • A donation of your time to take festive family photos with the lights/tree downtown
  • Chamber staff/volunteers would monitor the line and/or time slots, payment, etc. at the event.
  • An online link for those who purchase a photo that we can share through the emails that Chamber staff collects at the event
  • You can help design / set up the location and props for display


Our event dates (choose one or more that may work in your schedule):

  • November 19 – Turn on the Lights from 6-8 PM (lights come on at 6 PM)
  • December 2 – Merry Little Downtown Christmas from 5:30-7:30 PM
  • December 3 – Lighted Christmas Parade – 4-6 PM before the parade

If interested, please call 641-672-2591 or email

Each year, from late November to early January, Painting with Lights illuminates buildings around Oskaloosa’s historic downtown square and throughout the city. Painting with Lights is an Oskaloosa Main Street and Mahaska Chamber project. Our committee works hard to raise funds to support this annual $30,000 project.

Our dazzling display cannot continue or expand without financial support from the community—including our annual Painting with Lights raffle, which last year raised $8,000+ for Painting with Lights! We need your support to keep the lights glowing and to continue growing the lights in 2022 and beyond! 

Purchase your Painting with Lights Raffle Tickets at the Mahaska Chamber office, H&S Feed and Country Store, or Mahaska Drug until November 27. Drawing on November 28.

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