# Events & Things To Do in Winterset in October 2026 | AllEvents

- **Subtitle**: Find events and things to do in October 2026 in Winterset. Discover parties, concerts, meets, shows, sports, club, reunion, Performance happening in October 2026 in Winterset.
- **Category**: october
- **Display Name**: Events in October
- **Type**: time_filter

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## About

With a bunch of festivals in October 2026 in [CITY] queued up, there is a lot to catch on! From being a spectator at all the cool festivals to attending some interesting events in October in [CITY] there is all the fun awaiting you this month. Take a tour to this interesting guide or list of things to do in [CITY] in October 2026 and make the most of your holidays and weekends!

## october Events in Winterset

- **Event Name**: Decades on the Orchard
  - **Description**: Get ready to rewind. For one day only, we’re taking over the orchard with nonstop music from the 60s through the 2000s. Winterset, Iowa becomes the soundtrack of every era you love. From classic rock to 90s alt to early‑2000s emo anthems, each set is craf
  - **Interested Audience**:
    - Count: 211
  - **Date**: Sat Oct 17 2026 at 05:00 pm – Sat Oct 17 2026 at 11:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/decades-on-the-orchard/200029433699425
  - **Venue**: Winterset Cidery
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy8xYjJmYmZmNTdjMDM3NGVhODcwZGY4ZmI0MjI5MmFmMjVjOTQzMjljNjQ3OWY5ZmIxZDYwYTM0YTQ1ZDYyOTZjLXJpbWctdzEwODAtaDEwODAtZGNlZGRhYWEtZ21pcj92PTE3NzU1NjU0NTM.avif
  - **Categories**: food-drinks, kids

## Trending Events in Winterset

- **Event Name**: Madison County Fair Rodeo
  - **Description**: Get ready for an action-packed evening at the annual Madison County Fair Rodeo!

📅 Date: Saturday, June 13, 2026
🕢 Time: Rodeo begins at 7:30 PM
🐑 Mutton Bustin’: 7:00 PM (sign-up details coming soon)
📍 Location: Madison County Fairgrounds

Enjoy a night
  - **Venue**: Madison County Fair, Iowa
  - **Banner**: https://cdn-az.allevents.in/events3/banners/c4ae4ccdf9df903fe111fc4575d1778e7c44b23c0b12734da608465369e15b17-rimg-w1200-h675-dc8f765f-gmir?v=1775802219
- **Event Name**: Mother’s Day at Winterset Cidery
  - **Description**: Your mom wants cider, flowers, and live music at Winterset Cidery! 🌸🍎

Plan a fun day with the moms in your life—I’m pretty sure they’ll be happy if it includes relaxing in the beautiful sunshine, next to the orchard, with a glass of crisp, refreshing cid
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-az.allevents.in/events9/banners/36b250853a7ac1b61633e61d898e247d7b93f2d875df4b6fc61a60e6a3211537-rimg-w1080-h1080-dcd2c6c3-gmir?v=1775000040
- **Event Name**: Fly Iowa Festival 2026
  - **Description**: Join us for an unforgettable day of aviation, community, and celebration at the Fly Iowa Festival 2026!

📅 Saturday, September 19, 2026
⏰ 2:00 PM – 9:00 PM
📍 Winterset Airport (3Y3) – Winterset, Iowa
🎟️ FREE ADMISSION

Experience the sights and sounds of
  - **Venue**: Winterset Municipal Airport
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- **Event Name**: Madison county fair truck pull 2026
  - **Description**: Mark your calendars for the Madison county fair truck pull July 15th 2026 at 7:00 PM. We plan to make it bigger and better every year for the pullers, keep an eye out for our post in the near future with rules and payouts! We plan to have BIG PAYOUTS this
  - **Venue**: Madison County Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events1/banners/1a7ca4d49f7cfc3c6a747be71621046475429d7bb1d1aac5038994dc21ae4f7c-rimg-w878-h1560-dca49279-gmir?v=1768677585
- **Event Name**: Live Music at Winterset Cidery 5.23.26
  - **Description**: Join us Saturday, May 23rd for an evening of great music, delicious food, and amazing cider at Winterset Cidery!

Jesse and The Medicine Men are back and playing live from 5–8pm, bringing the perfect soundtrack to your Saturday night.

We’ll be open 1–10p
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-az.allevents.in/events10/banners/81b231dbf7f7beb90308c8602bca0c27bf943cede51c6ac923ad69e8612a023c-rimg-w1080-h1080-dcc0bcc0-gmir?v=1774669220
- **Event Name**: Decades on the Orchard
  - **Description**: Get ready to rewind. For one day only, we’re taking over the orchard with nonstop music from the 60s through the 2000s. Winterset, Iowa becomes the soundtrack of every era you love. From classic rock to 90s alt to early‑2000s emo anthems, each set is craf
  - **Venue**: Winterset Cidery
  - **Banner**: https://cdn-az.allevents.in/events3/banners/1b2fbff57c0374ea870df8fb42292af25c94329c6479f9fb1d60a34a45d6296c-rimg-w1080-h1080-dceddaaa-gmir?v=1775565453
- **Event Name**: 2nd Annual Ken Burk Car Cruise
  - **Description**: Rev your engines, it’s time for the 2nd Annual Ken Burk Car Cruise!

Join us June 6! All cars are welcome — whether you’re rolling in a vintage beauty or your everyday ride.

📍 Meet at the Jackson Building (1146 W. Summit St.) by 3:00 PM
🛣 Cruise paved ro
  - **Venue**: Madison County Historical Complex
  - **Banner**: https://cdn-az.allevents.in/events5/banners/f8d6b65a80445c05a4726add87e468f3fb210c5cc4b2dcb72b02d4066b0e6b14-rimg-w940-h788-dc181817-gmir?v=1775558495
- **Event Name**: RUNWAY ON 2ND: Sip. See spring trends. Shop the square.
  - **Description**: Runway on 2nd
Sip. See. Shop the Square.

Brought to you by the Winterset Retail District! 

Join us for a stylish spring morning Runway on 2nd is a curated fashion preview showcasing local boutiques and businesses in an elevated, welcoming setting at The
  - **Venue**: 231 N 2nd Ave, Winterset, IA, United States, Iowa 50273
  - **Banner**: https://cdn-az.allevents.in/events6/banners/77676c30a4626a5fcf7ed6219aa3c8285f91dc848975ac9b1d6657f33ef56bbc-rimg-w1200-h675-dc323236-gmir?v=1775558459
- **Event Name**: Witches!? In Salem?! Dinner Theater
  - **Description**: Set in the shadowy days of Salem, Massachusetts, this immersive production invites you to enjoy a delicious, family-style meal while the drama unfolds around you. Accusations fly, tensions rise, and secrets simmer just beneath the surface as you become pa
  - **Venue**: The Warehouse on 2nd
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## Browse october Events by Date

- [october Events Today in Winterset](https://allevents.in/winterset/october--today)
- [october Events This Weekend in Winterset](https://allevents.in/winterset/october--this-weekend)
- [october Events in April in Winterset](https://allevents.in/winterset/october--april)
- [october Events in May in Winterset](https://allevents.in/winterset/october--may)

## FAQs

- **Q**: What are the top october events in Winterset?
  - **A:** Decades on the Orchard (Sat Oct 17 2026 at 05:00 pm at Winterset Cidery).
- **Q**: How can I find october events in Winterset?
  - **A:** You can discover upcoming october events in Winterset on AllEvents.in. Browse by date, venue, or price to find events that match your interests.
- **Q**: How do I buy tickets for october events in Winterset?
  - **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 october events in Winterset?
  - **A:** Some popular venues hosting october events in Winterset include Winterset Cidery.
- **Q**: Who are the top organizers for october events in Winterset?
  - **A:** Popular organizers hosting october events in Winterset include Unfiltered Events.
- **Q**: Are there any online october events available?
  - **A:** Yes, many october 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 october events in Winterset?
  - **A:** Follow the october category on AllEvents.in to get notified when new october events are listed in Winterset.

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