# Events & Things To Do In Winterset This Weekend | June 12-14, 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

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- **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**: Madison County Line / Music at the Winery
  - **Description**: In conjunction with Paint Madison County : A Plein Air Festival  Madison County Line band will be playing live music at public reception & art sale from 3-6PM.  

Americana Band Covering the Classics from the 60's, 70's, and 80's. The Stones, The Who,
  - **Interested Audience**:
    - Count: 86
  - **Date**: Sun Jun 14 2026 at 03:00 pm – Sun Jun 14 2026 at 06:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/madison-county-line-music-at-the-winery/200030077983142
  - **Venue**: 2207 170th Drive, Winterset, IA, United States, Iowa 50273
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  - **Categories**: music, entertainment, festivals, live-music, art, music-festivals
- **Event Name**: Live Music at Winterset Cidery 6.14.26
  - **Description**: Join us for Sunday Funday at Winterset Cidery as we welcome back Corey Jamison!

We’re open 1–6pm, with live music from Corey Jamison from 2–5pm, and the Hotsy Totsy food truck serving up a delicious dinner from 2–5pm.

Cider will be flowing, vibes will b
  - **Interested Audience**:
    - Count: 26
  - **Date**: Sun Jun 14 2026 at 01:00 pm – Sun Jun 14 2026 at 06:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/live-music-at-winterset-cidery-61426/200030042552534
  - **Venue**: 1638 Highway 169, Winterset, IA
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  - **Categories**: Music, Entertainment, food-drinks
- **Event Name**: MC Line at Covered Bridges Winery
  - **Description**: Join MC Line at Covered Bridges Winery as they wrap up Paint Madison County with an evening reception and art sale. Meet the artists, take home a one-of-a-kind piece celebrating Madison County, enjoy the atmosphere, and listen to Americana hits from the 6
  - **Interested Audience**:
    - Count: 99
  - **Date**: Sun Jun 14 2026 at 03:00 pm – Sun Jun 14 2026 at 06:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/mc-line-at-covered-bridges-winery/200029918493345
  - **Venue**: Covered Bridges Winery
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  - **Categories**: art
- **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: 132
  - **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
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  - **Categories**: art, festivals
- **Event Name**: GUN AUCTION
  - **Description**: TERMS: Cash or good check. Proper ID required for bidding number. Lunch served.
  - **Date**: Sun Jun 14 2026 at 12:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/gun-auction/200030228647243
  - **Venue**: 914 N 1st Avenue • Winterset, Iowa
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- **Event Name**: Men's day 2026
  - **Description**: Let's blow up a car and whatever else we want and then eat around 5 with a potluck and then do a bonfire, swimming and fishing.
  - **Interested Audience**:
    - Count: 75
  - **Date**: Sun Jun 14 2026 at 01:00 pm – Sun Jun 14 2026 at 11:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/mens-day-2026/200030098317633
  - **Venue**: 1742 190th St, Winterset, IA 50273-8517, United States
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  - **Categories**: sports, food-drinks, potluck

## Trending Events in Winterset

- **Event Name**: PepperHarrow Lavender Festival
  - **Description**: Join us at the height of lavender season! Each year, PepperHarrow Flower and Lavender Farm opens its gates for a rare and fleeting experience when the fields are in full bloom, and the air is perfumed with lavender.

Stroll through sweeping rows of lavend
  - **Venue**: 1809 S 4th Ave, Winterset, IA 50273-2908, United States
  - **Banner**: https://cdn-az.allevents.in/events5/banners/f09a052aa2a8f92ffcc8b23736ff0a7a903aeec076ffa31fe30605011ce40d6b-rimg-w1200-h1500-dca3d4ed-gmir?v=1781328218
- **Event Name**: Fly Iowa Festival 2026
  - **Description**: Join us for an unforgettable day of aviation, community, and celebration at the Fly Iowa Festival 2026!

UPDATE: Come see the famous YL-37 Flying Memorial and take a ride in a PT-19!! 

More aircraft announcements to come! 

📅 Saturday, September 19, 2026
  - **Venue**: Winterset Municipal Airport
  - **Banner**: https://cdn-az.allevents.in/events7/banners/a2e8240cae6c722f64d1eaa576d5334c02112463ad5761cdf0cb507f266ba958-rimg-w1200-h1649-dcdedacf-gmir?v=1780250737
- **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**: Clark Tower 100th Anniversary Celebration
  - **Description**: 🎉 Clark Tower 100th Anniversary Celebration Weekend 🎉
📅 August 7 & 8, 2026
📍 Winterset, Iowa

Join us as we celebrate 100 years of one of Winterset’s most treasured landmarks — Clark Tower! Built in 1926 and beloved by generations, Clark Tower has sto
  - **Venue**: Winterset City Park
  - **Banner**: https://cdn-az.allevents.in/events9/banners/ad774ce35c3a4ad58d7afe0266f6c5f0d1a3140de096fedc3c8fe93810eca525-rimg-w1200-h500-dcf3eadf-gmir?v=1781328229
- **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**: America 250 Community Concert
  - **Description**: 🎶 YOU’RE INVITED! 🇺🇸

Join the Madison County Community Choir for a special patriotic concert celebrating America 250 on Sunday, June 28 at 7:00 PM on the north lawn of the Madison County Historical Complex!

This 45–50 minute community event will feature
  - **Venue**: Madison County Historical Complex
  - **Banner**: https://cdn-az.allevents.in/events4/banners/31a07d3ffc4dc495197d06cdba7e766f241ddd218f10d6ee46e8952d5f59f347-rimg-w1200-h800-dcffffff-gmir?v=1781328227
- **Event Name**: Vineyard to Orchard: A Progressive Pairing
  - **Description**: Join us on Saturday, June 20th for a unique evening in partnership with Covered Bridges Winery!

Vineyard to Orchard: A Progressive Pairing

Experience the best of both worlds with this one-of-a-kind ticketed event featuring both Covered Bridges Winery an
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-az.allevents.in/events6/banners/e997117290ff91d746c6d74c44f2ca130874429e16c111826d3d65effc15a03b-rimg-w1200-h1552-dc354658-gmir?v=1780460790
- **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=1777565262
- **Event Name**: Independence Day at Winterset Cidery 7.4.26
  - **Description**: The 4th of July at Winterset Cidery sounds like the best time to us!!🍎

Join us on Saturday, July 4th from 1-10pm for a full day of fun at the cidery! We’ll have live music by the talented Amanda Pruitt Duo from 5-8pm, delicious charcuterie boxes availabl
  - **Venue**: 1638 Highway 169, Winterset, IA
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## 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 June in Winterset](https://allevents.in/winterset/this-weekend--june)
- [Weekend Events in July in Winterset](https://allevents.in/winterset/this-weekend--july)

## FAQs

- **Q**: What are the top Weekend events in Winterset?
  - **A:** Madison County Line / Music at the Winery (Sun Jun 14 2026 at 03:00 pm at 2207 170th Drive, Winterset, IA, United States, Iowa 50273), Live Music at Winterset Cidery 6.14.26 (Sun Jun 14 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), MC Line at Covered Bridges Winery (Sun Jun 14 2026 at 03:00 pm at Covered Bridges Winery), Paint Madison County - A Plein Air Festival (Sun Jun 14 2026 at 09:00 am at 73 Jefferson Street, Winterset, IA, United States, Iowa 50273), GUN AUCTION (Sun Jun 14 2026 at 12:00 pm at 914 N 1st Avenue • Winterset, Iowa).
- **Q**: What Weekend events are happening in Winterset today June 14, 2026?
  - **A:** Madison County Line / Music at the Winery (Sun Jun 14 2026 at 03:00 pm at 2207 170th Drive, Winterset, IA, United States, Iowa 50273), Live Music at Winterset Cidery 6.14.26 (Sun Jun 14 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), MC Line at Covered Bridges Winery (Sun Jun 14 2026 at 03:00 pm at Covered Bridges Winery), Paint Madison County - A Plein Air Festival (Sun Jun 14 2026 at 09:00 am at 73 Jefferson Street, Winterset, IA, United States, Iowa 50273), GUN AUCTION (Sun Jun 14 2026 at 12:00 pm at 914 N 1st Avenue • Winterset, Iowa).
- **Q**: What Weekend events are happening in Winterset this weekend June 12–14, 2026?
  - **A:** Madison County Line / Music at the Winery (Sun Jun 14 2026 at 03:00 pm at 2207 170th Drive, Winterset, IA, United States, Iowa 50273), Live Music at Winterset Cidery 6.14.26 (Sun Jun 14 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), MC Line at Covered Bridges Winery (Sun Jun 14 2026 at 03:00 pm at Covered Bridges Winery), Paint Madison County - A Plein Air Festival (Sun Jun 14 2026 at 09:00 am at 73 Jefferson Street, Winterset, IA, United States, Iowa 50273), GUN AUCTION (Sun Jun 14 2026 at 12:00 pm at 914 N 1st Avenue • Winterset, Iowa).
- **Q**: What Weekend events are happening in Winterset in June 2026?
  - **A:** Madison County Line / Music at the Winery (Sun Jun 14 2026 at 03:00 pm at 2207 170th Drive, Winterset, IA, United States, Iowa 50273), Live Music at Winterset Cidery 6.14.26 (Sun Jun 14 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), MC Line at Covered Bridges Winery (Sun Jun 14 2026 at 03:00 pm at Covered Bridges Winery), Paint Madison County - A Plein Air Festival (Sun Jun 14 2026 at 09:00 am at 73 Jefferson Street, Winterset, IA, United States, Iowa 50273), GUN AUCTION (Sun Jun 14 2026 at 12:00 pm at 914 N 1st Avenue • Winterset, Iowa).
- **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 2207 170th Drive, Winterset, IA, United States, Iowa 50273, 1638 Highway 169, Winterset, IA, Covered Bridges Winery.
- **Q**: Who are the top organizers for Weekend events in Winterset?
  - **A:** Popular organizers hosting Weekend events in Winterset include Covered Bridges Winery, Winterset Cidery, Madison County Line.
- **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.

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