Sunday, February 22nd, 2026
Danny Grause / Music at the Winery
- Music from 2-4 PM
Event will be outdoors, weather permitting.
Danny Grause will delight us with a great mix of country, blues, funk, and rock. For fans of Chris Stapleton, Zac Brown Band & Eric Church.
Saturday, March 7th, 2026
Knit-and-Sip
- 1:00 – 4:00 pm
Join us for a “knit-and-sip” at Covered Bridges Winery in Winterset! Get cozy while you craft your own chunky knit blanket. We’ll provide step-by-step guidance and helpful instructions suitable for all skill levels. Blanket size will range from a lap throw to twin-sized, based on how tightly you choose to knit the yarn. The price includes 4 skeins of yarn in your choice of yarn colors (see below). Additional skeins can be purchased WHEN REGISTERING for $10/each.
Covered Bridges Winery has charcuterie and other snacks available for purchase!
Sunday, March 8th, 2026
Devon Miller / Sunday Wine Down
- Live Music 2-4 PM
- No Cover Charge, if you like what you hear please tip the musician.
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, March 28th, 2026
Looking4Luke / Music at the Winery
- 6:30-9:30 pm
- $5 Cover Charge per person at the door.
Matthew Kiger, Mark Christensen & John O’Neal; Three guys playing acoustic music ranging from classic rock, pop & country to some of today’s hit songs. As a group, we enjoy singing music that all ages can sit back & enjoy. Come on out to hear songs from artists like Eric Clapton, Elvis Presley, The Eagles, up to current acts like Little Big Town, Ed Sheeran & more.
Sunday, March 29th, 2026
Aaron Simmons / Sunday Wine Down
- Live Music by Aaron Simmons from 2-4 PM
- No Cover Charge. If you like what you hear, please tip the musician.
Originally from Stewartville, Minnesota, Aaron Simmons is a country singer-songwriter known for energetic performances and heartfelt storytelling. With a down-to-earth style and strong work ethic, he’s spent the past decade building a loyal fanbase nationwide.
In 2024, Aaron was named Male Vocalist of the Year by the Midwest Country Music Organization, after previous nominations for Song, Album, and Male Vocalist of the Year. His debut album, Third St SW, reached #5 on the iTunes Country Albums Chart in 2020, and his 2023 follow-up, Center Avenue, solidified his place in the genre. Songs like “Nobody’s Home in Wadena” and “Soldier in a Frame” earned regional praise, with the former topping Spotify’s Local Pulse: Minneapolis chart.
Aaron’s songs capture the joys of love, the pain of loss, and the power of community. With strong small-town values and a close connection to fans, he continues to make his mark in modern country music.
He’s performed across the Midwest and beyond—including New England, Tennessee, Michigan, Nebraska, Missouri, and Mississippi—and opened for acts like Scotty McCreery, Parmalee, Tracy Byrd, Easton Corbin, Matt Stell, Elvie Shane, and Restless Road.
Sunday, June 14th, 2026
Paint Madison County – A Plein Air Festival
- 9:00 AM – 1:00 PM | Watch Artists at Work
- 3:00 PM – 6:00 PM | Reception & Art Sale
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 evening before) around Madison County and watch youth and adult artists create original works inspired by our historic charm, covered bridges, and beautiful landscapes.
🎨 3:00 PM – 6:00 PM | Reception & Art Sale
Join us at Covered Bridges Winery for an evening reception and art sale. Meet the artists, enjoy the atmosphere, and take home a one-of-a-kind piece celebrating Madison County.
Youth and Adult Artists are welcome to participate. Applications are required: https://www.exploremadisoncounty.com/…/pain…/2026-06-13/
The Reception & Sale is open to the public — come out, support local artists, and celebrate creativity in Madison County!
“Today’s Agenda: 1) Open. 2) Pour. 3) Sip. 4) Rest under a tree.”