Come out and enjoy an evening of live music and great cider in the beautiful Madison County countryside with Slipstream.

Slipstream performs favorite classic rock and pop hits from the 70’s to today.  Focusing on Great music that everyone knows.  Awesome vocals with 2 female and 2 male lead singers.  A unique experience because their mix of instruments and vocals allows them to do music that few other bands can match.

$5 Cover Charge

All Children attending must be accompanied by an adult at all times

No pets allowed on Live Music Saturday

Come out and enjoy an evening of live music and great cider in the beautiful Madison County countryside with the 1st Name Band.

1st Name Band is a duo-acoustic cover band of classic country greats, classic rock, 90's alt-rock, 90's rap turned acoustic, modern pop turned acoustic, traditional Irish, and Disney songs

$5 Cover Charge

All Children attending must be accompanied by an adult at all times

No pets allowed on Live Music Saturday

Come out and enjoy an evening of live music and great cider in the beautiful Madison County Countryside with a local favorite, Crosswind.

Crosswind is a six piece band based out of Winterset, Iowa that performs a variety of music including tunes of the Eagles, The Beatles, George Strait, Pat Benatar, Bon Jovi and various other bands from the 50’s thru the 80’s.

$5 Cover Charge

All Children attending must be accompanied by an adult at all times

No pets allowed on Live Music Saturday

Come out and enjoy an evening of live music and great cider in the beautiful Madison County countryside with Nate Nelson and The State Street Band.

Take a day off from the state fair and head to Winterset. Nate & the boys will be back together on stage for just one event.

$5 Cover Charge

All Children attending must be accompanied by an adult at all times

No pets allowed on Live Music Saturday

Come out and enjoy and evening of live country music and great cider in the beautiful Madison County countryside with local favorite Western Outlaws!

$5 Cover Charge

All children attending must be accompanied by an adult at all times

No pets allowed on Live Music Saturday

Come out and enjoy an evening of live music and great cider in the beautiful Madison County countryside with Hold On.

Hold on is a premier cover/dance band playing classic rock spanning 5 decades – a professional, energetic show you can’t get enough of! Very fun and engaging.

And hang around until the end for our annual fireworks show!

$5 Cover Charge

All Children attending must be accompanied by an adult at all times.

No pets allowed on Live Music Saturday

Come out and enjoy an evening of live music and great cider in the beautiful Madison County countryside with Brick Imerman

Playing everything from classic rock to rocking country, and tasty blues to originals.

$5 Cover charge

All Children attending must be accompanied by an adult at all times.

No pets allowed on Live Music Saturday

Come out and enjoy an evening of live music and great cider in the beautiful Madison County countryside with Red Dirt Renegade.

Come enjoy an amazing evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!
Enjoy the flavors cooked up by Up in Smoke! and the music by RED DIRT RENEGADES
Red Dirt Renegades are a 5 piece band that features a real Oklahoma cowboy on lead vocals, 3 part harmonies and a pedal steel guitarist that's a member of the Bluegrass Hall of Fame. They play an energetic set of modern Outlaw country like Chris Stapleton, Jamey Johnson, Cody , Blackberry Smoke and classics by Waylon Jennings, Johnny Cash, Hank Williams Jr, Lynyrd Skynyrd and Marshall Tucker Band.

$5 Cover charge

All Children attending must be accompanied by an adult at all times.

No pets allowed on Live Music Saturday

Come out and enjoy an evening of live music and great cider in the beautiful Madison County country side and help us celebrate another great season with the Robbie Michael Band .

The Robbie Michael Band plays a wide variety of genres, with a solid foundation in Country

$5 Cover Charge

All children attending must be accompanied by an adult at all times

No pets allowed on Live Music Saturday

Come out and enjoy an evening of live music and great cider in the beautiful Madison County countryside with Zachary Freedom.

Three words describe Zach: Passion, Real, Inspiring. Zach’s style of music is nothing short of fresh. Zach will captivate you with a voice influenced by soul, pop, and a unique blend of his own stuff. From pop to rock, to blues & ballads there is something in Zach’s arsenal of music that will truly move you.

$5 Cover charge

All Children attending must be accompanied by an adult at all times.

No pets allowed on Live Music Saturday

Come celebrate another great season and enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!

Enjoy the flavors cooked up by Up in Smoke! and the music by BRICK ‘N BOB DUO

No, they aren’t a law firm or domestic partners, they are a great party band from Central Iowa. Playing everything from classic rock to rocking country, and tasty blues to originals. They play it all from the 1950’s to now. It is straight up sing-along and dance music – no crying in your hard cider allowed with Brick ‘n Bob.

There is a $5 cover charge.  Bring a lawn chair as outdoor seating is limited. 

Note:  Children attending the event must be with their parents at all times and no pets are allowed on event nights.

Come enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!

Enjoy the flavors cooked up by Up in Smoke! and the music by HOLD ON

A premier cover/dance band playing classic Rock spanning 5 decades – a professional, energetic show you can’t get enough of! Very fun & engaging.

There is a $5 cover charge.  Bring a lawn chair as outdoor seating is limited. 

Note:  Children attending the event must be with their parents at all times and no pets are allowed on event nights.

Due to weather forecast we are cancelling tonights Live Music.

Come enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!

Enjoy the flavors cooked up by Up in Smoke! and the music by CROSSWIND

Crosswind is a six-piece band based out of Winterset, Iowa that performs a variety of music. Their music includes tunes from The Eagles, Carly Simon, George Strait, Marshall Tucker, Bon Jovi and various other bands from the 50’s thru the 80’s. 

There is a $5 cover charge.  Bring a lawn chair as outdoor seating is limited. 

Note:  Children attending the event must be with their parents at all times and no pets are allowed on event nights.

Come enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!

Enjoy the flavors cooked up by Up in Smoke! and the music by NATE NELSON & THE STATE STREET BAND

Yes, it’s true!! A reunion is in the making. Take a day off from the Iowa State Fair and head down to Winterset. Nate and the boys will be back together on stage for just one event.

Come enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!

Enjoy the flavors cooked up by Up in Smoke! and the music by iNFUZiON

iNFUZiON is a Des Moines power trio comprised of members Kevin McGinnis, Greg Cloe and Mark Owen. iNFUZiON plays a wide variety of songs - everything from Tom Petty, to Van Morrison, Kenny Rogers, Eric Clapton, The Rolling Stones, Waylon & Willie, CCR, The Kinks, The Meters, The Grateful Dead, and the list goes on and on. 

This will also be a night of fundraising for the Madison County Sheriff's K-9 Unit to help with the cost of continued training, vet bills and other expenses that arise.

Come enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!

Enjoy the flavors cooked up by Up in Smoke! and the music by The Red Dirt Renegades.

Red Dirt Renegades are a 5 piece band that features a real Oklahoma cowboy on lead vocals, 3 part harmonies and a pedal steel guitarist that's a member of the Bluegrass Hall of Fame. They play an energetic set of modern Outlaw country like Chris Stapleton, Jamey Johnson, Cody , Blackberry Smoke and classics by Waylon Jennings, Johnny Cash, Hank Williams Jr, Lynyrd Skynyrd and Marshall Tucker Band.

Come enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!

Enjoy the flavors cooked up by Up in Smoke! and the music by HOLD ON

Hold On is a premier cover/dance band playing classic Rock spanning 5 decades – a professional, energetic show you can’t get enough of! Very fun & engaging.

Come enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!

Enjoy the flavors cooked up by Up in Smoke! and the music by Kaleena

Canadian-born singer/song writer, Kaleena has been carving out her place in Central Iowa soul music…exploring the unique place where folk and singer/song writer tendencies meet the soulful, upbeat corners of R & B (while) providing a sense of moodiness & atmosphere.

Come enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider at Winterset Cidery!

Enjoy the flavors cooked up by Up in Smoke! and the music by Brick 'n Bob Duo

No, they aren’t a law firm or domestic partners, they are a great party band from Central Iowa. Playing everything from classic rock to rocking country, and tasty blues to originals. They play it all from the 1950’s to now. It is straight up sing-along and dance music – no crying in your hard cider allowed with Brick ‘n Bob.

Come celebrate opening weekend of our 2018 season and enjoy a fun evening of good food, great music and amazing locally made Hard Apple Cider! Enjoy the flavors cooked up by Up in Smoke and music by Zachary Freedom.

Three words to describe Zach: Passion, Real & Inspiring. Zach’s style of music is nothing short of fresh. Zach will captivate you with a voice influenced by soul, pop and a unique blend of his own stuff. From pop to rock and blues to ballads there is something in Zach’s arsenal of music that will truly move you.