# Live Music in Winterset 2026 | Gigs, Bands & Concerts

- **Subtitle**: Discover live music in Winterset. Book tickets for gigs, band performances, jazz nights and live concerts happening across the city. Find your next show today.
- **Category**: Live Music
- **Type**: other

## Audience

- **Followers**: 1.1M+
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## About

For the ones whose heart beats for music, live music events are something that you will absolutely enjoy. Groove on the most upbeat songs and enjoy the best of live music in [CITY]. You will find music of all kinds and genres, discover the ones that fit your interests and enjoy the spellbinding surroundings near you. You will be in a constant dilemma what to choose and what to drop, because there is music beating all around the city. From jazz nights at the jazz clubs to soulful musical events at the best live music venues in [CITY].
Discover all the mesmerizing and all the heavy & loud music events near you.

## Live Music Events in Winterset

- **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
  - **Date**: Sat Apr 25 2026 at 06:30 pm – Sat Apr 25 2026 at 09:30 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/velvet-trio-covered-bridges-winery/200029931217544
  - **Venue**: Covered Bridges Winery
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9kZjhiYWJhZjg0MGNjYTA2ZmJkOWZlMjRmODZiYjYxNjIzODcyZmIzZGQ1NzNjNjdhZjM2NzhhNDQ5MDY3MGI2LXJpbWctdzEyMDAtaDgwMC1kYzE4MTYxNy1nbWlyP3Y9MTc3NTk3MTcyMw.avif
  - **Categories**: Music, Workshops, Entertainment
- **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**: 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
  - **Interested Audience**:
    - Count: 69
  - **Date**: Sat Jun 06 2026 at 03:00 pm – Sat Jun 06 2026 at 07:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/2nd-annual-ken-burk-car-cruise/200029884175546
  - **Venue**: Madison County Historical Complex
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy9mOGQ2YjY1YTgwNDQ1YzA1YTQ3MjZhZGQ4N2U0NjhmM2ZiMjEwYzVjYzRiMmRjYjcyYjAyZDQwNjZiMGU2YjE0LXJpbWctdzk0MC1oNzg4LWRjMTgxODE3LWdtaXI_dj0xNzc1NTU4NDk1.avif
  - **Categories**: Business
- **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.

Grab your lawn chairs, bring your favorite people, a
  - **Interested Audience**:
    - Count: 17
  - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy8xNTY1ZDU4Njc0ZjA4MTg3MmExYmEyNzQzZDFmNjJlYWIzNzE4N2VkMjVhZWU2YTQxMGJhZTQxMzJhOWMwZThmLXJpbWctdzEwODAtaDEwODAtZGNjNGMyYmQtZ21pcj92PTE3NzQ2MTEzNzc.avif
  - **Categories**: music, live-music, entertainment, holiday
- **Event Name**: Live Music at Winterset Cidery 4.18.26
  - **Description**: Join us on Saturday, April 18th from 1–10pm at Winterset Cidery! 🍎

Cider will be flowing all day, live music by Royce Johns Duo from 5–8pm, and delicious eats from Snappy’s BBQ from 5–8pm!

$5 cover per vehicle, no matter how many people.

Grab your frie
  - **Interested Audience**:
    - Count: 176
  - **Date**: Sat Apr 18 2026 at 01:00 pm – Sat Apr 18 2026 at 10:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/live-music-at-winterset-cidery-41826/200029770303149
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9hMjc3NGU4YmE3MzkxNDEzMTBlMTYyNDNhODlkNWQ2NTkxZWVlN2ZjMmI4NmQ1M2E0ZjRmNWVjNmIwZGI4ZjFhLXJpbWctdzEwMDAtaDg1MC1kYzAwMDAwMC1nbWlyP3Y9MTc3NTA2NzU0NA.avif
  - **Categories**: music, live-music, entertainment
- **Event Name**: Sip & Sojurn
  - **Description**: Join us for an evening of inspiration and refreshment!

Reka Luxury Travel is heading to the beautiful Winterset Cidery for a special pop-up event. Whether you’re dreaming of a Mediterranean cruise, a private villa in Tuscany, or a seamless family getaway
  - **Interested Audience**:
    - Count: 9
  - **Date**: Sat Apr 18 2026 at 05:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/sip-and-sojurn/200029904460706
  - **Venue**: Winterset Cidery
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy80YTQxN2JmYjI2MmIxNzNkNDMxY2E0YWZhMzU5YzNmNDAxYmRiMTlmNzU2NWY3MTU2MTA2NDMzMDFiZmI3MjAzLXJpbWctdzEyMDAtaDY3NS1kY2ZmZmZmZi1nbWlyP3Y9MTc3NTU1ODQ2NQ.avif
  - **Categories**: music, live-music, trips-adventures, entertainment, pop-ups, meetups, meet-and-greet
- **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**: Live Music at Winterset Cidery
  - **Description**: May 31st — aka Sunday Funday — has arrived once again! 🍎☀️

We love that it comes around every week, and Winterset Cidery is here to help you wrap up your weekend in the best way possible. Join us from 1–6pm for cold, crisp cider, live music by Jake Schro
  - **Interested Audience**:
    - Count: 23
  - **Date**: Sun May 31 2026 at 01:00 pm – Sun May 31 2026 at 06:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/live-music-at-winterset-cidery/200029853550945
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9kYWMwMzQ1NWNiNDYxMTdkYmRlNzgxZmRkMGYwMjZjNzZmNTcwOWQ5MWFmMTI4NmY0ZmFmOGM1YTk3MGU1MzEyLXJpbWctdzEwODAtaDEwODAtZGNhYmE4YTMtZ21pcj92PTE3NzUwNDM4Mzg.avif
  - **Categories**: music, live-music, entertainment
- **Event Name**: Live Music at Winterset Cidery 5.2.26
  - **Description**: Your Saturday plans are set! 🍎

Join us at Winterset Cidery for a full day of crisp, refreshing cider and great company! We’ll be open 1–10pm, so come hang out for the afternoon or stay for the evening fun.

• Live music by Tony Bohnenkamp | 5–8pm
• Snapp
  - **Interested Audience**:
    - Count: 96
  - **Date**: Sat May 02 2026 at 01:00 pm – Sat May 02 2026 at 10:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/live-music-at-winterset-cidery-5226/200029853728836
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9mMTQ4MzI5MzMxOWRmOThlM2NiNjJjMTkzYWI3YTk3OGEyZDZiYmUzYzgzODU2ZTExOTRkNjg1NDEwNzliYzJjLXJpbWctdzEwODAtaDEwODAtZGNiZGJkYmMtZ21pcj92PTE3NzQzMzM1MzY.avif
  - **Categories**: music, live-music, entertainment
- **Event Name**: Live Music at Winterset Cidery 5.17.26
  - **Description**: Sunday Funday is back at Winterset Cidery!

Join us on May 17th from 1–6pm for an afternoon of great vibes, cold, crisp cider, and live entertainment. Zachary Freedom will be playing from 2–5pm, and Hotsy Totsy will be serving up delicious eats during the
  - **Date**: Sun May 17 2026 at 01:00 pm – Sun May 17 2026 at 06:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/live-music-at-winterset-cidery-51726/200029869532946
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy8yZWRiNzA2MjU0MmZiODVjZmZkY2ZlYzc0N2M0MTY3NTViZjUyMWY3NTIzZmE0ZmI3MjU0MjIxYzE4YzM2ZjlhLXJpbWctdzEwODAtaDEwODAtZGNhM2EzYTMtZ21pcj92PTE3NzQ2NjkyNDY.avif
  - **Categories**: Music, Entertainment
- **Event Name**: Fridays at The Farm
  - **Description**: Farm store opens at 5pm, music 🎶 by Willie Mac and The Lost Cousins from 6-9.  food by our Featured Barnyard Cooks The Hawkins! Covered Bridges Wine will be available for purchase by the bottle in the farm store or you are welcome to BYOB.  $5/ cover char
  - **Interested Audience**:
    - Count: 77
  - **Date**: Fri Jul 17 2026 at 05:00 pm – Fri Jul 17 2026 at 09:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/fridays-at-the-farm/200029785615617
  - **Venue**: 1578 North River Trail, Winterset, IA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8xN2RjNWI3MzA2MzhjN2M4MzU3ZDRhYmYyMzYwMjdkODdkODM5MmRiNDE2MmQ2MGQwNWU1ZDg4MjhiNmMyYWVmLXJpbWctdzEyMDAtaDEyMDAtZGNmZmZmZmYtZ21pcj92PTE3NzU0MjA1NTc.avif
- **Event Name**: Live Music at Winterset Cidery 4.19.26
  - **Description**: Sunday Funday is calling!

Join us at Winterset Cidery on April 19th from 1–6pm and enjoy live music by David Watson from 2–5pm. Cold cider, great music, and the perfect way to spend your Sunday!
  - **Interested Audience**:
    - Count: 37
  - **Date**: Sun Apr 19 2026 at 01:00 pm – Sun Apr 19 2026 at 06:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/live-music-at-winterset-cidery-41926/200029802880735
  - **Venue**: 1638 Highway 169, Winterset, IA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy9lOWZkZTgxOWMwYmVmZTQ4NmUwZGQxYWE1ODUxOGIwNjk4Njg1OGZhZDU3ODM1MjQyNjQxZmNjZWVlYzI4NjAxLXJpbWctdzEwMDAtaDg1MC1kYzAxMDEwMS1nbWlyP3Y9MTc3NDY3MDM1NA.avif
  - **Categories**: music, live-music, entertainment
- **Event Name**: Rural Route/ Sunday Wine Down
  - **Description**: Live Music from 2-4PM  No cover charge if you like what you hear please tip the musicians.  
Rural Route is bringing a two piece acoustic band to the winery.  They will bring to life some of your country favorites with some rock and alternative added in!
  - **Date**: Sun May 31 2026 at 02:00 pm – Sun May 31 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/rural-route-sunday-wine-down/200029918496502
  - **Venue**: 2207 170th Drive, Winterset, IA, United States, Iowa 50273
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy81OGY3MTU1OWYwMGJkMzY2ZmM3NzcwNjAzNzYxMWFhNmJiMGU5MzRmOTcwYzE1NjAxNTY1OTkxODc0ZWE0YjQwLXJpbWctdzEyMDAtaDE1NTMtZGMwMDAwMDAtZ21pcj92PTE3NzU4MDIyNDI.avif
  - **Categories**: Music, Entertainment
- **Event Name**: Jesse & The Medicine Men
  - **Description**: $5 Cover Charge per person. Live Music from 6:30-9:30PM
Join us on the patio for a wonderful evening of country music by the best.  Jesse & The Medicine Men will entertain us with some great tunes.
  - **Interested Audience**:
    - Count: 7
  - **Date**: Sat May 30 2026 at 06:30 pm – Sat May 30 2026 at 09:30 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/jesse-and-the-medicine-men/200029918493947
  - **Venue**: 2207 170th Drive, Winterset, IA, United States, Iowa 50273
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy83MjQzOTE1MWIyNjU4Zjc1ZDk0MzFkOTlkN2QxZjEzZWI1NjQ4NDE0YzhmODI0YTBiYmI0OGEzY2YwN2RmMGE2LXJpbWctdzc5MC1oNzkyLWRjMDIwMTAyLWdtaXI_dj0xNzc1ODAyMjI3.avif
  - **Categories**: music, live-music, entertainment, country-music-festivals
- **Event Name**: Moors & McCumber / Sunday Wine Down
  - **Description**: Live Music from 2-4PM 
No Cover Charge if you like what you hear please tip the musicians. 
"A vocal harmony duo fifteen years in the making, Moors & McCumber have done more than just endear themselves to fans - they’ve built a genuine community. Brid
  - **Interested Audience**:
    - Count: 44
  - **Date**: Sun Apr 19 2026 at 02:00 pm – Sun Apr 19 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winterset/moors-and-mccumber-sunday-wine-down/200029814249512
  - **Venue**: 2207 170th Drive, Winterset, IA, United States, Iowa 50273
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvZjA0NzQ5NGM4ZWRjNTI3MTlkZTk1ZTlkMGY4YzEyY2IxODVkZWZhM2Q1ODQ4OTBkN2YyZmNjNmMyMmYwMmY4OC1yaW1nLXc4MDAtaDYyNS1kYzAyMDIwMi1nbWlyP3Y9MTc3NTk3MTczMQ.avif
  - **Categories**: music, entertainment, live-music

## 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 Live Music Events by Date

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

## FAQs

- **Q**: What are the top Live Music events in Winterset?
  - **A:** Velvet Trio @ Covered Bridges Winery (Sat Apr 25 2026 at 06:30 pm at Covered Bridges Winery), Live Music at Winterset Cidery 5.23.26 (Sat May 23 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), 2nd Annual Ken Burk Car Cruise (Sat Jun 06 2026 at 03:00 pm at Madison County Historical Complex), Live Music at Winterset Cidery 5.24.26 (Sun May 24 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Live Music at Winterset Cidery 4.18.26 (Sat Apr 18 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA).
- **Q**: What Live Music events are happening in Winterset this weekend April 17–19, 2026?
  - **A:** Live Music at Winterset Cidery 4.18.26 (Sat Apr 18 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Sip & Sojurn (Sat Apr 18 2026 at 05:00 pm at Winterset Cidery), Live Music at Winterset Cidery 4.19.26 (Sun Apr 19 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Moors & McCumber / Sunday Wine Down (Sun Apr 19 2026 at 02:00 pm at 2207 170th Drive, Winterset, IA, United States, Iowa 50273).
- **Q**: What Live Music events are happening in Winterset in April 2026?
  - **A:** Velvet Trio @ Covered Bridges Winery (Sat Apr 25 2026 at 06:30 pm at Covered Bridges Winery), Live Music at Winterset Cidery 4.18.26 (Sat Apr 18 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Sip & Sojurn (Sat Apr 18 2026 at 05:00 pm at Winterset Cidery), Live Music at Winterset Cidery 4.19.26 (Sun Apr 19 2026 at 01:00 pm at 1638 Highway 169, Winterset, IA), Moors & McCumber / Sunday Wine Down (Sun Apr 19 2026 at 02:00 pm at 2207 170th Drive, Winterset, IA, United States, Iowa 50273).
- **Q**: How can I find Live Music events in Winterset?
  - **A:** You can discover upcoming Live Music 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 Live Music 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 Live Music events in Winterset?
  - **A:** Some popular venues hosting Live Music events in Winterset include Covered Bridges Winery, 1638 Highway 169, Winterset, IA, Madison County Historical Complex.
- **Q**: Who are the top organizers for Live Music events in Winterset?
  - **A:** Popular organizers hosting Live Music events in Winterset include Velvet Trio, Winterset Cidery, Reka Luxury Travel.
- **Q**: What types of Live Music events can I find in Winterset?
  - **A:** You can explore a variety of live music sub-genres and styles including Hip Hop Music, House Music, Classical Music, Afrobeats, Bachata and more.
- **Q**: Are there any online Live Music events available?
  - **A:** Yes, many Live Music 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 Live Music events in Winterset?
  - **A:** Follow the Live Music category on AllEvents.in to get notified when new Live Music events are listed in Winterset.

## Live Music from nearby cities

- [Live Music in St Charles](https://allevents.in/st-charles-ia/live-music)
- [Live Music in Saint Charles](https://allevents.in/saint-charles-ia/live-music)
- [Live Music in Cumming](https://allevents.in/cumming-ia/live-music)
- [Live Music in Dexter](https://allevents.in/dexter-ia/live-music)
- [Live Music in Adel](https://allevents.in/adel-ia/live-music)