Saturday, September 12th, 2026
Madison County Line/ Music at the Winery
- $5 Cover Charge per person at the door
- Live Music by 6:30-9:30PM
- Hey Mister’s Feast Fare serving from 5:30-8:00PM
Americana Band Covering the Classics from the 60’s, 70’s, and 80’s. The Stones, The Who, Gordon Lightfoot, John Denver, Johnny Cash, Jimmy Buffett, The Band, The Animals, Eric Clapton, Marshall Tucker Band, Van Morrison, Tom Petty, CCR, America, Eagles
Sunday, September 20th, 2026
Dan Medeiros / Sunday Wine Down
- Live music from 2-4PM
- No cover charge if you like what you hear please tip the musicians.
The Dan Medeiros Project is the creative endeavor of singer-songwriter Dan Medeiros, known for his distinctive blend of alternative and rock music. Born and raised in the suburbs of Toronto, Canada, Dan was immersed in a musical environment from a young age, with a family rich in musical talent.
In March 2012, Dan relocated to Des Moines, Iowa, where he established himself as a solo artist within the local music scene. His official debut solo album, “Forever & After,” was released in 2015. Over the next several years, Dan performed over 100 shows annually across the Midwest, captivating audiences with his unique use of 12-string acoustic guitars and a vocal range that transitions seamlessly from soft and haunting to gritty and powerful.
On March 10, 2024, Dan released his debut single and music video, “DREAMS,” produced in collaboration with Misha Olson at Speed of Sound in Des Moines. The song achieved significant acclaim, winning “Best Music Video” and “Best Inspirational Song” at the 3rd Annual Iowa Music Awards. The music video, directed by Dan himself, was also highlighted among the best Iowa music videos of 2024 by Iowa Public Radio.
Sunday, September 27th, 2026
Madison County Fall Crawl
- Will be happening from 8AM to 6PM
The Madison County Fall Crawl is a small, local event near Winterset, IA that takes place on the last Sunday in September.
Take a drive with friends around Madison County to see 15 small local businesses in their rural setting. There are a few stops along the crawl that have normal business hours where you can grab a glass of coffee, wine, cider, beer, or a bite to eat.
The fall crawl is a free event for the entire family, with lots of fun things to do with live music, kid’s activities, 80+ vendors and food trucks. Earliest businesses opening at 9am. Varies by stop location.
Sunday, September 27th, 2026
Looking 4 Luke / Sunday Wine Down
- Live Music from 1-4PM
- No cover charge if you like what you hear please tip the musicians.
Looking 4 Luke is an energetic cover trio performing a wide variety of genres and musical generations with a decidedly unplugged feel.
Sunday, October 4th, 2026
Corbett Reeves / Sunday Wine Down
- Music from 2-4PM
- No cover charge if you like what you hear please tip the musicians.
Corbett has been a constant presence in the DSM metro for over a decade, playing acoustic guitar and singing at festivals, bars, churches, private parties…basically any place with a stage. His honest take on new and old classics blends an Iowan’s desire to do it right with a Louisiana native’s penchant to break the rules. His setlist which includes Rock, Folk, and Americana, with a sprinkling of his own soulful originals, will help you remember why your favorite songs are still your favorite songs.
Sunday, October 18th, 2026
Devon Miller / Sunday Wine Down
- Live Music from 2-4PM
- No cover charge if you like what you hear please tip the musicians.
Devon Miller has been playing guitar for 46 years. He grew up playing country and bluegrass with his dad’s band and had his first on stage experience at the age of 12. For the last 26 years he’s been playing and singing classic rock all across the state of Iowa.
His approach to acoustic shows is to play a little of everything. Country, rock, pop, blues, folk, bluegrass, even tv show themes and comedy songs. Any genre is fair game. If it’s a good song, Devon probably plays it.
“One of my favorite parts of a gig is when a member of the audience requests a random song that I don’t normally do, but I’m familiar enough with it that I can look up the lyrics and play it for them right on the spot. Many times that song will be such a hit with the audience that it will become a regular part of the set.”
Devon loves playing, singing and interacting with the audience. You’re bound to have a great time at one of his shows.
Saturday, October 24th, 2026
Willie Mac & The Lost Cousins/ Music at the Winery
- $5 Cover Charge Per Person
- Live Music from 6:30-9:30PM
- Hey Mister Feast Fare food truck from 5:30 – 8:30.
- Music will be outdoor weather permitting.
Willie Mac and the band will perform an infusion of bluegrass, folk-rock and blues.
“Today’s Agenda: 1) Open. 2) Pour. 3) Sip. 4) Rest under a tree.”