# Events & Things To Do In Winterset This Weekend | May 22-24, 2026| AllEvents

- **Subtitle**: Winterset is a city full of experiences, activities and events. Explore some of the best things to do in Winterset this weekend and make your Friday, Saturday and Sunday full of fun and excitement.
- **Category**: Weekend
- **Display Name**: Events this weekend
- **Type**: time_filter

## Audience

- **Followers**: 20.7k+
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## About

Weekends become special if you know how to make the most out of it. There are a lot of fun things to do and events in [CITY] this weekend for you to explore.

Make your weekends memorable. Check out all upcoming weekend events in [CITY].

## Weekend Events in Winterset

- **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
  - **Interested Audience**:
    - Count: 111
  - **Date**: Sat May 23 2026 at 01:00 pm – Sat May 23 2026 at 10:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/live-music-at-winterset-cidery-52326/200029824566816
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvODFiMjMxZGJmN2Y3YmViOTAzMDhjODYwMmJjYTBjMjdiZjk0M2NlZGU1MWM2YWM5MjNhZDY5ZTg2MTJhMDIzYy1yaW1nLXcxMDgwLWgxMDgwLWRjYzBiY2MwLWdtaXI_dj0xNzc0NjY5MjIw.avif
  - **Categories**: music, live-music, entertainment
- **Event Name**: Live Music at Winterset Cidery 5.24.26
  - **Description**: Join us Sunday, May 24th from 1–6pm for a holiday weekend Sunday Funday at Winterset Cidery! 🇺🇸🍎

Kick back, relax, and sip on crisp, refreshing cider while enjoying live music by Kris Karr from 2–5pm and charcuterie by Graze Craze.

Grab your lawn chairs
  - **Interested Audience**:
    - Count: 44
  - **Date**: Sun May 24 2026 at 01:00 pm – Sun May 24 2026 at 06:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/live-music-at-winterset-cidery-52426/200029833297308
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy8xNTY1ZDU4Njc0ZjA4MTg3MmExYmEyNzQzZDFmNjJlYWIzNzE4N2VkMjVhZWU2YTQxMGJhZTQxMzJhOWMwZThmLXJpbWctdzEwODAtaDEwODAtZGNjNGMyYmQtZ21pcj92PTE3Nzg0NDY4NzI.avif
  - **Categories**: music, live-music, entertainment, holiday
- **Event Name**: Mulberry Farm & Food Truck @Madison County Farmers Market
  - **Description**: Come get some grub at the Madison County Farmers Market!
  - **Interested Audience**:
    - Count: 2
  - **Date**: Sat May 23 2026 at 08:00 am – Sat May 23 2026 at 12:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/mulberry-farm-and-food-truck-madison-county-farmers-market/200030023990118
  - **Venue**: 112 S John Wayne Dr, Winterset, IA 50273, United States
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  - **Categories**: food-drinks, farmers-markets
- **Event Name**: Opening Day @ Speckled Hen Farms
  - **Description**: Join us for opening day @ SHF! Join us for tasty samples of our "famous" homemade bread, farm favorite dip mixes, fresh finds, seasonal goodies & all the cozy farm charm you've been missing!  Get a FREE SHF tote with a $50 purchase (* while they last!
  - **Interested Audience**:
    - Count: 298
  - **Date**: Sat May 23 2026 at 11:00 am – Sat May 23 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/opening-day-speckled-hen-farms/200029785616324
  - **Venue**: 1578 North River Trail, Winterset, IA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvMTM5MmYwNTRhMDc2NDYxNjM2Yjc2Yjc1ZDIyYjdjMjk5YmNiMmI5YzdkYjk5ZGI0NTEyZmUxNDgyNzNhMjYzOS1yaW1nLXcxMjAwLWgxMjAwLWRjMTIxNDE4LWdtaXI_dj0xNzc5MTU2NDcx.avif
- **Event Name**: Siena’s Graduation Open House
  - **Description**: Just wanted to get the date out there. We’ve had a couple people ask for planning purposes. Physical invite will be mailed when it gets closer.
  - **Interested Audience**:
    - Count: 24
  - **Date**: Sat May 23 2026 at 09:30 am – Sat May 23 2026 at 12:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/siena’s-graduation-open-house/200029918498414
  - **Venue**: Winterset Community Church
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- **Event Name**: Addy’s Grad Party
  - **Description**: Come celebrate Addy in the Community Room at USB as we celebrate her graduation from WHS and launch in the fall to the University of Northern Iowa. She has worked so hard, now it is time to sit back, relax and enjoy some time of celebration of all of that
  - **Interested Audience**:
    - Count: 29
  - **Date**: Sat May 23 2026 at 01:00 pm – Sat May 23 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/addy’s-grad-party/200029884176201
  - **Venue**: Union State Bank
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  - **Categories**: parties, entertainment

## Trending Events in Winterset

- **Event Name**: Beginner Sourdough Workshop at Winterset Cidery
  - **Description**: You asked and now you shall receive!

The last 3 Beginner Sourdough Workshops have been a huge hit, so we’re excited to add a FOURTH class! Join us and Counter Culture Sourdough Co on Friday, June 12th from 6:30–8:30pm for another Beginner Sourdough Work
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-az.allevents.in/events3/banners/b570c15aedaa81a775c9b8186acdfa0c1843a9f90f56296c60faa8d23333f7d4-rimg-w1080-h1080-dcf1efed-gmir?v=1778448474
- **Event Name**: Spring Kick-Start 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-dc91775f-gmir?v=1779137286
- **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=1777524681
- **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**: 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=1778249719
- **Event Name**: A Picnic in the Forest
  - **Description**: Escape to the peaceful woods of Iris Aisle for an evening of elegant dining and whimsical charm.About this EventWelcome to A Picnic in the Forest!Date:
  - **Venue**: Iris Aisle
  - **Banner**: https://cdn-az.allevents.in/events4/banners/5287fadcbf1219dac92bcccc0af57010487b57b1773333ad38bf4e5380623820-rimg-w1200-h800-dc32452f-gmir.jpg?v=1779143898
- **Event Name**: Winterset Cidery 10 Year Anniversary
  - **Description**: Winterset Cidery is incredibly blessed and excited to celebrate 10 years in business!

For the past decade, we’ve been crafting hard apple cider right here in Winterset, Iowa. What started as a vision from Gary Heck grew into the beautiful orchard and one
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-az.allevents.in/events3/banners/de874bb7dab7f45b8cf3835ca87dadfc8a03f29c87936ca770ce44c112a9516e-rimg-w1200-h1013-dceae7e0-gmir?v=1779166547
- **Event Name**: Quilting and the Art of What If
  - **Description**: Tony will be presenting his "Quilting and the Art of What If" talk at Covered Bridges Winery on Friday, June 5th in conjunction with the Iowa Quilt Festival put on by the Iowa Quilt Museum. Tickets must be purchased from Covered Bridge Winery at: https://
  - **Venue**: 54 E Court Ave, Winterset, IA, United States, Iowa 50273
  - **Banner**: https://cdn-az.allevents.in/events3/banners/743b2534ae074679550f4700a345d5855a94a125fbe14ac6656643e4c3f3e99b-rimg-w648-h916-dcc2bbc2-gmir?v=1778354040
- **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

## Browse Weekend Events by Date

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

## FAQs

- **Q**: What are the top Weekend events in Winterset?
  - **A:** Live Music at Winterset Cidery 5.23.26 (Sat May 23 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Live Music at Winterset Cidery 5.24.26 (Sun May 24 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Mulberry Farm & Food Truck @Madison County Farmers Market (Sat May 23 2026 at 08:00 am at 112 S John Wayne Dr, Winterset, IA 50273, United States), Opening Day @ Speckled Hen Farms (Sat May 23 2026 at 11:00 am at 1578 North River Trail, Winterset, IA), Siena’s Graduation Open House (Sat May 23 2026 at 09:30 am at Winterset Community Church).
- **Q**: What Weekend events are happening in Winterset this weekend May 22–24, 2026?
  - **A:** Live Music at Winterset Cidery 5.23.26 (Sat May 23 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Live Music at Winterset Cidery 5.24.26 (Sun May 24 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Mulberry Farm & Food Truck @Madison County Farmers Market (Sat May 23 2026 at 08:00 am at 112 S John Wayne Dr, Winterset, IA 50273, United States), Opening Day @ Speckled Hen Farms (Sat May 23 2026 at 11:00 am at 1578 North River Trail, Winterset, IA), Siena’s Graduation Open House (Sat May 23 2026 at 09:30 am at Winterset Community Church).
- **Q**: What Weekend events are happening in Winterset in May 2026?
  - **A:** Live Music at Winterset Cidery 5.23.26 (Sat May 23 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Live Music at Winterset Cidery 5.24.26 (Sun May 24 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Mulberry Farm & Food Truck @Madison County Farmers Market (Sat May 23 2026 at 08:00 am at 112 S John Wayne Dr, Winterset, IA 50273, United States), Opening Day @ Speckled Hen Farms (Sat May 23 2026 at 11:00 am at 1578 North River Trail, Winterset, IA), Siena’s Graduation Open House (Sat May 23 2026 at 09:30 am at Winterset Community Church).
- **Q**: How can I find Weekend events in Winterset?
  - **A:** You can discover upcoming Weekend 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 Weekend 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 Weekend events in Winterset?
  - **A:** Some popular venues hosting Weekend events in Winterset include 1638 Highway 169, Winterset, IA, 112 S John Wayne Dr, Winterset, IA 50273, United States, 1578 North River Trail, Winterset, IA.
- **Q**: Who are the top organizers for Weekend events in Winterset?
  - **A:** Popular organizers hosting Weekend events in Winterset include Winterset Cidery, Mulberry Farm & Food Truck, Speckled Hen Farms Iowa.
- **Q**: Are there any online Weekend events available?
  - **A:** Yes, many Weekend 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 Weekend events in Winterset?
  - **A:** Follow the Weekend category on AllEvents.in to get notified when new Weekend events are listed in Winterset.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/01/bac113436441a783feaca7074943a8/this-weekend.webp

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