Sunday, May 17th, 2026
Ava Lemon / Sunday Wine Down
- Live Music 2-4 PM
- No Cover Charge, if you like what you hear please tip the musician.
Ava Lemon is a passionate and expressive singer-songwriter from the Midwest state of Iowa. Blending folk and alt-pop influences, she sings meaningful songs with a soulful voice that speaks directly to the heart.
Saturday, May 30th, 2026
Jesse & The Medicine Men
- Live Music from 6:30-9:30PM
- $5 Cover Charge per person
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.
Sunday, May 31st, 2026
Rural Route / Sunday Wine Down
- Live Music 2-4 PM
- No Cover Charge, if you like what you hear please tip the musician.
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! They also have plenty of originals you are guaranteed to have fun at the show.
Friday, June 5th, 2026
Quilting & the Art of What If
5-7 PM
Nationally known quilt designer, Tony Jacobson, will be presenting his program “Quilting and the Art of What If.” In this hour-long presentation he will show you how to look at patterns in a different light. He will be present around 40 quilts showing you how different the same pattern can look by changing the colors, style of fabrics, and even switching up the values of the fabrics used in the background and the main prints. He will also show how making minor alterations to a block can make a big difference in the look of the quilt. You will come away inspired to make every pattern uniquely yours.
Tony Jacobson is a former graphic designer/art director for 30 years with his last art director position being for Fons & Porter’s Love of Quilting Magazine. He is currently the Owner & Creativity Director for Piece Works Quilt Shop in Winterset, Iowa where he is constantly coming up with new patterns for the shop. Digital patterns can be found at PieceWorksQuiltShop.com/shop.
Piece Works Quilt Shop will be supplying gift bags for all those who pre-register for the program. Door prizes will also be given throughout the night. Covered Bridges Winery will supply a glass of wine (or beverage of your choice) and an individual charcuterie plate for all who pre-register as well. $5 of each ticket purchased will be donated to the Iowa Quilt Museum located in Winterset, Iowa.
Saturday, June 6th, 2026
The Barrelhouse Rockets
- Live Music from 6:30-9:30PM
- $5 Cover Charge per person
- Backroads Grill Food Truck serving 5:30 to 8:00 pm
Music will be outdoors weather permitting. Bring your lawn chairs as seating is limited. The Barrelhouse Rockets are Midwest rockabilly, known for their electrifying live performances. With a lineup of seasoned musicians, they deliver high-energy & upbeat rockin’ boogie-woogie that gets the crowd moving every time.
Sunday, June 14th, 2026
Paint Madison County – A Plein Air Festival
- 9:00 AM – 1:00 PM | Watch Artists at Work
- 4:00 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.
🎨 4:00 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!
Sunday, June 14th, 2026
Madison County Line/Music at the Winery
- Live Music from 3PM to 6PM
- In conjunction with Paint Madison County : A Plein Air Festival Madison County Line band will be playing live music at public reception & art sale
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, June 21st, 2026
Matt Woods Roots Music/Sunday Wine Down
- Live Music 2-4PM
- No Cover Charge
- If you like what you hear please tip the musician.
Music will be outdoor weather permitting. Bring your lawn chairs as seating is limited. Come out relax and listen to some fabulous blues tunes by Matt Woods.
Saturday, June 27th, 2026
KRACKLIN/ Music at the Winery
- $5 Cover Charge per person at the door
- Live Music from 6:30-9:30PM
- Music will be outdoors weather permitting. Bring your lawn chairs as seating is limited.
Food for sale by the Winterset Japanese Exchange program (pork sandwich’s and side) Kracklin is a fun acoustic duo performing classic rock, pop-country and even TV show themes! David and Sara have been delighting crowds for 5 years in the Des Moines area with their exemplary vocals and wide range of songs. You won’t find anyone else quite like them!
“Today’s Agenda: 1) Open. 2) Pour. 3) Sip. 4) Rest under a tree.”