# Festivals in Winterset | Cultural Events & Fairs

- **Subtitle**: Explore upcoming festivals in  Winterset. Discover cultural celebrations, street fairs and seasonal events happening across the city. Join the festivities.
- **Category**: Festivals
- **Type**: category

## Audience

- **Followers**: 2.5M+
- **Recent Followers**: 
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## About

The best things to do in the world include attending top-notch festivals in [CITY]. Be it a rocking music festival or scrumptious food festival in [CITY], you will have a gala time of your life with a few of your close friends or your family. With the best of fun, entertainment, and food, the experience in festivals lets the enthusiasts immerse in the local culture and vibe. Ranging from the biggest outdoor beach parties to crazy music festivals, the festivals fall under various categories to suit everybody’s tastes. If you are looking for the best events and festivals in [CITY] listed on one platform - we have you covered.

Immerse yourself in the mega dance festivals, electrifying music festivals, theatre & film festivals, quirky local festivals and more with us!

## Festivals Events in Winterset

- **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
  - **Interested Audience**:
    - Count: 1827
  - **Date**: Sat Sep 19 2026 at 02:00 pm – Sat Sep 19 2026 at 09:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/fly-iowa-festival-2026/200029788672423
  - **Venue**: Winterset Municipal Airport
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9hMmU4MjQwY2FlNmM3MjJmNjRkMWVhYTU3NmQ1MzM0YzAyMTEyNDYzYWQ1NzYxY2RmMGNiNTA3ZjI2NmJhOTU4LXJpbWctdzEyMDAtaDE2NDktZGNkZWRhY2YtZ21pcj92PTE3NzYxMzU0Njk.avif
  - **Categories**: festivals, kids, workshops, trips-adventures, fireworks, calendar
- **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
  - **Interested Audience**:
    - Count: 118
  - **Date**: Sat Jun 13 2026 at 07:30 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/madison-county-fair-rodeo/200029918492640
  - **Venue**: Madison County Fair, Iowa
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9jNGFlNGNjZGY5ZGY5MDNmZTExMWZjNDU3NWQxNzc4ZTdjNDRiMjNjMGIxMjczNGRhNjA4NDY1MzY5ZTE1YjE3LXJpbWctdzEyMDAtaDY3NS1kYzhmNzY1Zi1nbWlyP3Y9MTc3NTgwMjIxOQ.avif
  - **Categories**: rodeo, festivals
- **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
  - **Interested Audience**:
    - Count: 148
  - **Date**: Wed Jul 15 2026 at 07:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/madison-county-fair-truck-pull-2026/200029341358504
  - **Venue**: Madison County Fairgrounds
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy8xYTdjYTRkNDlmN2NmYzNjNmE3NDdiZTcxNjIxMDQ2NDc1NDI5ZDdiYjFkMWFhYzUwMzg5OTRkYzIxYWU0ZjdjLXJpbWctdzg3OC1oMTU2MC1kY2E0OTI3OS1nbWlyP3Y9MTc2ODY3NzU4NQ.avif
  - **Categories**: calendar
- **Event Name**: Middle River Arts Festival
  - **Description**: The Winterset Art Center is pleased to invite everyone to The Middle River Arts Festival, a one-day, free public event hosted at the Madison County Conservation Center (MCCC) on Saturday, May 2nd, from 10:00 am to 4:00 pm.

The Madison County Conservatio
  - **Interested Audience**:
    - Count: 142
  - **Date**: Sat May 02 2026 at 10:00 am – Sat May 02 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/middle-river-arts-festival/200029841570835
  - **Venue**: 2508 Pammel Park Trl, Winterset, IA 50273-8308, United States
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy84YzhmNDExNzAxZGMyOTZiMDQxODc0Y2VjNTExY2U5MzIwNWQ0NDVlNThjZWFmZGEzYjc4NzZiM2Y3ZTAwM2Q5LXJpbWctdzcxNC1oNzI3LWRjMmQzMTJlLWdtaXI_dj0xNzc1NTM4MzY3.avif
  - **Categories**: art, festivals, fine-arts, trips-adventures
- **Event Name**: Winterset Porchfest 2026
  - **Description**: It's January and you know what that means??  We have our Winterset Porchfest date set!!!  SAVE THE DATE - Winterset Porchfest 2026 will be held on SUNDAY AUGUST 30TH!!!  Watch for more updates and more details coming soon - New things happening this secon
  - **Interested Audience**:
    - Count: 360
  - **Date**: Sun Aug 30 2026 at 11:00 am – Sun Aug 30 2026 at 06:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/winterset-porchfest-2026/200029613938539
  - **Venue**: Winterset, Iowa
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9mMjdiMmE3YWQ3ZDRiYzgxNGQzYzFhZTk2MzE3MTY4NDc0ODE0ZGI0YTVkNDA5Yzc5YmZmZWUxNmI3OTg5OGJiLXJpbWctdzY0MC1oNjQwLWRjZmZmZmZmLWdtaXI_dj0xNzc1NjY2NjE4.avif
- **Event Name**: Paint Madison County - A Plein Air Festival
  - **Description**: Paint Madison County – A Plein Air Festival
Experience Madison County through the eyes of talented artists during this one-day plein air festival!

🖌 9:00 AM – 1:00 PM | Watch Artists at Work
Visit various scenic locations (locations will be released the
  - **Interested Audience**:
    - Count: 83
  - **Date**: Sun Jun 14 2026 at 09:00 am (-05:00)
  - **Event URL**: https://allevents.in/winterset/paint-madison-county-a-plein-air-festival/200029684525227
  - **Venue**: 73 Jefferson Street, Winterset, IA, United States, Iowa 50273
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy8zYWFhMjk5NTA3ODgzZTg3ZWEwZWQ3NmFlYzk2ZTZiNmZjYjhiYTA1MjVmZjIxOTBlZmY4ZDc3YWIwMDdkOTZmLXJpbWctdzg1MS1oMzE1LWRjZmZmZmZmLWdtaXI_dj0xNzc1NDk3Mjkw.avif
  - **Categories**: art, festivals

## Trending Events in Winterset

- **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
  - **Banner**: https://cdn-az.allevents.in/events7/banners/a2e8240cae6c722f64d1eaa576d5334c02112463ad5761cdf0cb507f266ba958-rimg-w1200-h1649-dcdedacf-gmir?v=1776135469
- **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**: 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**: 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**: Velvet Trio @ Covered Bridges Winery
  - **Description**: Join Velvet Trio, at Covered Bridges Winery, on Saturday, April 25th for an evening of good vibes, smooth live music, and of course plenty of WINE! 
The music starts at 6:30 but be sure to get there early and grab a good table!  They always go fast!
Hope
  - **Venue**: Covered Bridges Winery
  - **Banner**: https://cdn-az.allevents.in/events3/banners/df8babaf840cca06fbd9fe24f86bb61623872fb3dd573c67af3678a4490670b6-rimg-w1200-h800-dc181617-gmir?v=1775971723
- **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**: 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**: 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

## Browse Festivals Events by Date

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

## FAQs

- **Q**: What are the top Festivals events in Winterset?
  - **A:** Fly Iowa Festival 2026 (Sat Sep 19 2026 at 02:00 pm at Winterset Municipal Airport), Madison County Fair Rodeo (Sat Jun 13 2026 at 07:30 pm at Madison County Fair, Iowa), Madison county fair truck pull 2026 (Wed Jul 15 2026 at 07:00 pm at Madison County Fairgrounds), Middle River Arts Festival (Sat May 02 2026 at 10:00 am at 2508 Pammel Park Trl, Winterset, IA 50273-8308, United States), Winterset Porchfest 2026 (Sun Aug 30 2026 at 11:00 am at Winterset, Iowa).
- **Q**: How can I find Festivals events in Winterset?
  - **A:** You can discover upcoming Festivals 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 Festivals 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 Festivals events in Winterset?
  - **A:** Some popular venues hosting Festivals events in Winterset include Winterset Municipal Airport, Madison County Fair, Iowa, Madison County Fairgrounds.
- **Q**: Who are the top organizers for Festivals events in Winterset?
  - **A:** Popular organizers hosting Festivals events in Winterset include Winterset Municipal Airport, Madison County Fair, Iowa, Winterset Art Center.
- **Q**: Are there any online Festivals events available?
  - **A:** Yes, many Festivals 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 Festivals events in Winterset?
  - **A:** Follow the Festivals category on AllEvents.in to get notified when new Festivals events are listed in Winterset.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/6e/5415e403f74b77938c0695ac11464e/Festival.jpg

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