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

Our summer events have concluded and all I can say is "WOW!", Oskaloosa - you showed up for this amazing community!  From kicking off summer at a damp Art on the Square to standing in what seemed like mile-long lines at Sweet Corn Serenade, you showed up!  It was my first time coordinating these events and I loved it. Planning and implementing these awesome events is something that brings me great joy!  August brought the Iowa State Fair and anyone who knows me well  knows that I LOVE the state fair!  I've camped at the fair since I was 4 months old.  I am thankful for the opportunity to take some time off and experience the fair with my family - we enjoyed our fair share of cheese on a stick!

Upcoming Main Street Events

Oskaloosa Main Street's Committees have been working to plan our first-ever Upper Story Housing Tour. The ELEVATE your living upper story housing tour will take place on Saturday, October 1 between 10 AM-1 PM in various downtown locations.

Tickets are available now!  $10 for potential renters & general public. Downtown building owners, contractors, realtors, and investors are free but we are asking for RSVP.

Locations include:

  • Ratcliff & Blake Upper Story
  • Hunter's Upper Story
  • Brown's Shoe Fit Upper Story
  • Hawkeye Real Estate Upper Story
  • Untamed Nutrition Upper Story

The tour will be self-guided and you can visit as many stops as you'd like. Tickets can be purchased in advance from the Chamber office and Brown's Shoe Fit or at any stop on the day of the tour.

Main Street Committee Members and some building owners will be present to answer questions. We will also have refreshments at the Hawkeye Real Estate & Brown's Shoe Fit stops.

Full details can be found at

Window Art StoryWalk®

Plans are underway for a Halloween themed Window Art StoryWalk®.

A StoryWalk® is a fun, educational activity that places a children's story (literally a book taken apart) along a popular walking route in your community.

Participating Main Street businesses will have storyboards in their windows and local artists will paint on the windows to tie into the story. The featured story is, Mr. Pumpkin's Tea Party by Erin Barker.

Free make'n'take activities, coloring, snacks, 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. To prep for the holiday season, a canned food drive will be held during our Downtown Tea Party. Food donations will be delivered to the Ecumenical Food Cupboard.

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

Joe Crookham of Musco Lighting with a Sweet Deal in recognition of 46 years of business in the Main Street District.

Downtown Conference held in Pella

The Downtown Conference was held in Pella in early August. Oskaloosa/Mahaska County was represented very well with five Main Street Board/Committee Members and two staff present. It was a wonderful conference with lots of great information and ideas shared.

Pictured L-R:

Mike Gipple, Janet Hermsen,

Amy Brainard, Deann De Groot, Linda Crookham-Hansen, 

Beth Brostrom, Shawn Christ

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

Monday, November 28

Entry deadline TBA.

Window Decorating Contest

Wednesday, November 30

Thursday, December 1

Entries are due November 9.

Merry Little Downtown Christmas

Friday, December 2 6:00-7:00 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.

  • Downtown Resurfacing Project began in late July. This project will continue to cause short-term street closures in and around the Oskaloosa Main Street District. Visit for details or call our office with questions at 641-672-2591.
  • The 4 lane to 3 lane conversion started work on August 22. There was a delay due to needed additional materials. This work involves the removal and replacement of pavement markings, median construction at the RR tracks on A Avenue West, installation of a new traffic signal at Market and C Avenue, underground electric, adjusting the existing signal heads to be centered over the 3 lanes and a small portion of sidewalk work. Construction will start on A Avenue/IA 92 with outside lane closures across 2 intersections at a time progressing from west to east. The contractor will leave access to homes and business along the construction route at all times. Learn more at:
Oskaloosa Main Street | Website
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