Make your life happening by enrolling to entertainment events in [CITY]. Find a partner through a salsa night or take your partner to live in concerts by upcoming bands in your town. Get high while playing Beer Pong in a pub crawl or attending stand-up comedy events in [CITY]. Shake your legs in the happy streets, zumba or dance workshops or go for a film screening in the nearby cafes or theaters.
Explore Entertainment Events in [CITY].
## Entertainment Events in Oskaloosa - **Event Name**: All Alumni Reunion - **Description**: Thankful Thursday in The Alley 6/11/26 6:00-8:00. City Band Concert in the bandstand 6/11/26 at 8:00. Friday After Five 6/12/26 5:00-9:00 on the town square. Music by Wicked Ways. Art on the Square 6/13/26 9:00-3:00 - **Interested Audience**: - Count: 306 - **Date**: Thu Jun 11 2026 at 06:00 pm – Sat Jun 13 2026 at 03:00 pm (-05:00) - **Event URL**: https://allevents.in/oskaloosa/all-alumni-reunion/200029434636356 - **Venue**: Oskaloosa Town Square - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy8yNzg2N2MyMjIxNWQ2MjIxNWE3ZTY2OTUxOGE1ZmRiYmQxOGZiNDFiOGY5ODYzYTNhMGMyNWVkZGYyMWRkMzliLXJpbWctdzY2MC1oNjYwLWRjZmZmZmZmLWdtaXI_dj0xNzc1ODg2Mjk3.avif - **Categories**: music, entertainment, concerts, art ## Trending Events in Oskaloosa - **Event Name**: Pop-Up Park Picnic: Couple Date Night (Self-Guided) - Oskaloosa Area! - **Description**: Pop-Up Picnic in the Park Couple Date Night (Self-Guided) Watch sunset with fun digital activities over picnic!About this Eventhttps://youtu.be/3RnPhdEZLIIPOP-UP PICNIC IN THE PARK DATE NIGHT INCLUDES: - **Venue**: Edmundson Park - Recommended Park Venue or another park choice (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED) - **Banner**: https://cdn-az.allevents.in/events7/banners/30a8c353f4b780d87250037000a20c2c58c485e45ae7e2d693cc0e6f43363884-rimg-w612-h408-dc46491c-gmir.jpg?v=1760170950 - **Event Name**: Sweet Corn Serenade - **Description**: Join us for a long-time favorite community event! Oskaloosa Main Street’s annual Sweet Corn Serenade brings over 3,000 people to downtown Oskaloosa for fresh-cooked sweet corn and live music. This year’s festival will happen July 23, 2026, from 12 PM – 9 - **Venue**: Oskaloosa City Park and Band Stand - **Banner**: https://cdn-az.allevents.in/events10/banners/5c86f69416d2b78b4a3970de9608acd72900131426f9c591fc7533d886ce2344-rimg-w1200-h600-dcefa51c-gmir?v=1776287688 - **Event Name**: 57th Annual Art on the Square - **Description**: Join us in downtown Oskaloosa on Saturday, June 13, from 9 a.m. to 3 p.m. for the 57th Annual Art on the Square. Spend the day shopping for art, enjoying live demonstrations, and experiencing the creativity that makes this event a community favorite. Stop - **Venue**: City Square Park - **Banner**: https://cdn-az.allevents.in/events9/banners/a8f260f68ecd288b564f566017648d7d3063929340e63152dece38885bcac5b3-rimg-w940-h788-dc2e396f-gmir?v=1775899453 - **Event Name**: All Alumni Reunion - **Description**: Thankful Thursday in The Alley 6/11/26 6:00-8:00. City Band Concert in the bandstand 6/11/26 at 8:00. Friday After Five 6/12/26 5:00-9:00 on the town square. Music by Wicked Ways. Art on the Square 6/13/26 9:00-3:00 - **Venue**: Oskaloosa Town Square - **Banner**: https://cdn-az.allevents.in/events9/banners/27867c22215d62215a7e669518a5fdbbd18fb41b8f9863a3a0c25eddf21dd39b-rimg-w660-h660-dcffffff-gmir?v=1775886297 - **Event Name**: Oskaloosa Corn Belt Showdown - **Description**: A five-night stretch of racing in the Hawkeye State features a midweek visit to Oskaloosa for the biggest Late Model race in Southern Iowa Speedway history! - **Venue**: Southern Iowa Speedway - Osky - **Banner**: https://cdn-az.allevents.in/events1/banners/3ed879726188c073f3e3fa8ff7fe6f27cf80470576c19edb176bc420e68883db-rimg-w1200-h800-dc030609-gmir?v=1774272877 - **Event Name**: Old Settlers Reunion ( Alleyway Crafted Flavors Food Truck Pink ) - **Description**: Hello Oskaloosa! We will be rolling out our PINK truck at this event! In the pink truck, we will be serving mouth-watering soft pretzels and All Beef Hot Dogs along with all kinds of pickles! We won't have our famous lemonade due to other vendors but we - **Venue**: Oskaloosa Old Settlers Reunion - **Banner**: https://cdn-az.allevents.in/events3/banners/dd648fbe0caa18cd20e1d974ec502cc8ee9d1e4b673af52079daaa1dd5e3c32e-rimg-w1200-h800-dce53274-gmir?v=1775900555 - **Event Name**: Family Farm Day - **Description**: 🌾🚜 Family Farm Day is BACK at Waters Hardware! 🐓🌻 Mark your calendars for Saturday, April 25th from 9AM–3PM and bring the whole family out for a fun-filled day you won’t want to miss! 🐾 Meet adorable farm animals 🎨 Enjoy face painting & local vendor - **Venue**: 1007 Walnut St, Oskaloosa, KS 66066 - **Banner**: https://cdn-az.allevents.in/events5/banners/29f5770eb520cdd2884646189223f90ce697860f831e194776112c825ba8701e-rimg-w1200-h626-dc2da47a-gmir?v=1775854615 - **Event Name**: Mahaska County Saddle Club Open Show - **Description**: Join the Mahaska County Saddle Club on Saturday May 9th for our annual Jackpot Open Show! (Our rain date is June 21st - if we do not get rained out in May plan on coming to our fun show on June 21st!). This show also includes our QUEEN contest to choose - **Venue**: Southern Iowa Fairgrounds - **Banner**: https://cdn-az.allevents.in/events4/banners/cb388692949e645ed0da2f20407f50b7cb8803841d012d885858519a87d4f285-rimg-w960-h641-dc5e4532-gmir?v=1776433581 - **Event Name**: Shop The Alley - **Description**: Mark your calendars — Shop The Alley returns for our first show of the season! Stroll through downtown Oskaloosa and discover local crafters, makers, boutiques, and small businesses all in one fun outdoor market. It’s the perfect way to spend a spring Sat - **Venue**: Off Market St. Between Smokey Row and Bridal Dreams, Oskaloosa, IA, United States, Iowa 52577 - **Banner**: https://cdn-az.allevents.in/events2/banners/41ae2621eba3ef1151fafd756a540321727149a9b039e1f21729b92f8f7aec21-rimg-w960-h540-dcffffff-gmir?v=1776396609 ## Browse Entertainment Events by Date - [Entertainment Events Today in Oskaloosa](https://allevents.in/oskaloosa/entertainment--today) - [Entertainment Events This Weekend in Oskaloosa](https://allevents.in/oskaloosa/entertainment--this-weekend) - [Entertainment Events in April in Oskaloosa](https://allevents.in/oskaloosa/entertainment--april) - [Entertainment Events in May in Oskaloosa](https://allevents.in/oskaloosa/entertainment--may) ## FAQs - **Q**: What are the top Entertainment events in Oskaloosa? - **A:** All Alumni Reunion (Thu Jun 11 2026 at 06:00 pm at Oskaloosa Town Square). - **Q**: How can I find Entertainment events in Oskaloosa? - **A:** You can discover upcoming Entertainment events in Oskaloosa on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for Entertainment events in Oskaloosa? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: What are the popular venues for Entertainment events in Oskaloosa? - **A:** Some popular venues hosting Entertainment events in Oskaloosa include Oskaloosa Town Square. - **Q**: Who are the top organizers for Entertainment events in Oskaloosa? - **A:** Popular organizers hosting Entertainment events in Oskaloosa include The Alumni of Oskaloosa HS. - **Q**: Are there any online Entertainment events available? - **A:** Yes, many Entertainment events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new Entertainment events in Oskaloosa? - **A:** Follow the Entertainment category on AllEvents.in to get notified when new Entertainment events are listed in Oskaloosa. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/58/5efbefdb8e438db5c829e697673309/Maskgroup-3-.webp ## Entertainment events from nearby cities - [Entertainment events in Pella](https://allevents.in/pella/entertainment) - [Entertainment events in Delta](https://allevents.in/delta-ia/entertainment) - [Entertainment events in What Cheer](https://allevents.in/what-cheer/entertainment)