Events & Programs

The Oskaloosa area is home to numerous events and programs. For a complete list, check out the Team Mahaska calendar, featuring sporting events, club and organization meetings, and school activities. This brochure is our calendar of events that includes more highlighted upcoming events.

Annual Events


Featured Events

March 30
Business After Hours
TruBank, 302 S. Market
Chamber members, their families and friends, and community members are invited to attend a Business After Hours hosted by TruBank on Thursday, March 30 from 4:30pm to 6:30pm, refreshments will be served.

For more information please contact TruBank at 641-673-8405.
April 11
William Penn's Navy and Gold Gala
National Guard of Iowa Armory
Enjoy an evening of trivia under the tent at the National Guard of Iowa Armory in Oskaloosa. All funds raised will go to support scholarships for students. This year's event includes an interactive trivia contest, dinner, and night of friendly competition for friends of William Penn University. Tickets are $30 per person or $240 for an eight-person table. To reserve your seat or to reserve a table, contact William Penn Advancement at 641-673-1044. Seating is limited, so reserve your spot today. 
May 11
OACDG Annual Awards Banquet
William Penn Cafeteria
OACDG Annual Meeting to be held at William Penn Cafeteria, 5:00 - 6:30 social hour followed by dinner, awards, and dessert auction.  Call 641.672.2591 for tickets or to nominate award recipients.
May 12
Fall in Love With Junk
Southern Iowa Fairgrounds
641.673.7004 Southern Iowa Fairgrounds.
May 12
OACDG Scholarship Golf Tournament
Oskaloosa Golf
OACDG Scholarship Golf Tournament is set for Friday, May 12 with registration beginning at 9 am and shot-gun start at 10 am at Osky Golf.  Call 641.672.2591 to register your team by April 4.
June 9 - 10
Spring Festival
New Sharon
Come join us the weekend of June 9th for fun in the sun at New Sharon's Spring Festival. There will be many fun activities and food to go around. If you're ready to have some fun, please join us! For more information regarding our festival please look at our facebook page, New Sharon Spring Festival 2017 or email us at
June 9
Friday After Five
The Downtown Square
The event begins at 5 pm and goes until 10 pm. Sponsored by the Commerce Committee of the OACDG. Enjoy live music from Rich Webster Band & refreshments on the street in front of the Courthouse. For more info call 641.672.2591.
June 10
Main Street's Art on the Square
Downtown Oskaloosa
This juried art show and sale from 10 am to 4 pm includes children's activities, food vendors and more! Call 641.672.2591 for more information.  Purchase raffle tickets for chance to win $100 to $500 in purchase vouchers to spend at Art on the Square. Event will be in the historic square. Rain will bring the show to Penn Central Mall.
July 3 - 4
Stock Car Shootout
Southern Iowa Speedway
Call 641.673.7004
July 7
Friday After Five - Bandstand and Bikes
The Downtown Square
The event begins at 5 pm and goes until 10 pm. Sponsored by the Commerce Committee of the OACDG. Enjoy live music & refreshments downtown Oskaloosa. Ride your bike (motorized or not) downtown and enjoy sounds of live music from Fatal Addiction and Small Town Superheroes. For more info call 641.672.2591.
July 15
Christmas in July
The Square
11 am - 11 pm event to raise money for new Christmas lights in the downtown area. Event includes Children's crafts and family games from 11 - 3, followed by yard games, beverage garden, and live entertainment from 6 - 11 pm. A christmas Light Show at 9:30 pm. SEE YOU THERE! Sponsored by Main Street Oskaloosa.
July 17 - 22
Southern Iowa Fair
Fairgrounds, Oskaloosa
July 27
Main Street's Sweet Corn Serenade
Downtown Oskaloosa
Event is in the Oskaloosa Square from noon to 9 pm. It includes a craft & product show, live music, children's activities, pie baking contest, sweet corn, burger, pie, ice cream and MORE! Call 641.672.2591

Food, Craft, & Product Vendors...........Noon-9:00 pm
Sweet Corn & Beef Burgers..............4:00pm-Until we run out
Beef burgers by Mahaska County Cattlemen's Association. Meal-$5
Kid's Activities..............................4:00 pm
Fun with YMCA, Community 1st Train rides, Balloons by Terrific Tom,
Giant Slide, and Farm Bureau Agriculture Exhibit! 
Hawkeye Pedal Pull (ages 3-11)...................6:00 pm
Registration 5:30-6 pm only! Sponsors: McKim Tractors & Beck's Hybrids
Pie Baking Contest (Register at 5 at Bandstand)................5:30-7:30 pm
Two pies, one for contest and one to sell (fruit pie only, no cream pies).
Live Music.............5:30-7:30 pm
Sponsored by Bank Iowa
July 28 - 29
Rollin' Oldies Car Show/ Graffiti Night
Downtown Oskaloosa
Enjoy a magnificent display hosted by the Rollin' Oldies Car Club, 9 am - 3 pm in downtown Oskaloosa. Graffiti night is on Friday from 6 - 9 pm. Additional information please call John Ryken 641.673.4944
August 4
Friday After Five
Oskaloosa Downtown Square
Begins in Downtown Oskaloosa, 5-10 pm. Enjoy a live music and much more!
August 5
Run in the Sun 5K or 1-mile walk
Lacey Stadium
Proceeds go to Mahaska Health Partnership Hospice Serenity House. Register at by Mon. July 11. Call 641-672-3369.
October 13 - 13
Fall in Love With Junk Show
Southern Iowa Fairgrounds
Southern Iowa Fairgrounds. Call 641.673.7004 for more information regarding this event.
October 13 - 14
Osky Fall Challenge
Southern Iowa Speedway
Races at Iowa Southern Fairgrounds. For more information on this events please call, 641-673-7004.
October 31
Main Street's Trick or Treat Parade
Downtown Oskaloosa
Costumed children, parade in the downtown square, and events at Penn Central Mall. Bandstand at 4pm. Call 641-672-2591.

October 31
City-wide Trick or Treat
Oskaloosa, Iowa
City-wide Trick or Treat is from 6-8 pm in Oskaloosa on the 31th. Be SAFE!
November 27
Main Street's Young Ambassador Crowning
Penn Central Mall
Main Street's Young Ambassador Crowning: 6 pm at the Penn Central Mall. Call 641.672.2591.
Participants may enter up to Oct. 23. Voting is Nov. 1-30.
November 30
Holiday Market and Show
Penn Central Mall & the Oskaloosa Square
Event Starts at noon with a Holiday Market and a Festival of Trees Silent Auction in the Penn Central Mall. From 4-6 pm will also include gospel music, children's activities, train rides, Santa and Friends, and more. Gospel music will continue to 6:30 pm . Go to the square for the magnificent PAINTING WITH LIGHTS at 7 pm followed immediately by the Main Street Lighted Christmas Parade, "30 years of Christmas". Return to the warmth of the Mall after the parade for more gospel music (sponsored by Bank Iowa) at 8:30 pm Parade awards and tree auction results are set for 9:30 pm in the mall following the concert. 
November 30
Main Street Lighted Christmas Parade
Historic Downtown Oskaloosa
Main Street's Annual Christmas Parade: 30 years of Christmas Past, is the theme for the parade that will march through historic downtown Oskaloosa (Thursday only). Come see Santa and Mrs. Claus and their reindeer! Enjoy concessions, music, and more. Parade starts at 7:00 pm.
December 1
15th Year Main Street Holiday Luncheon & Show
The Peppertree
Main Street Holiday Luncheon & Show from 11:30 am to 1:00 pm at The Peppertree, Highway 63 North. Sponsored by Oskaloosa Main Street. Call 641-672-2591 for ticket information and reservations. Deadline Nov. 28.
©2017 Oskaloosa Area Chamber & Development Group
222 First Avenue East · Oskaloosa, Iowa 52577
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