From Winchester to Nashville and back again

Published 11:42 am Friday, June 9, 2023

Performing Bluegrass music has been a staple of Winchester natives Brenna and Theo MacMillan’s lives since the two were young.

They often graced the stage during September’s Daniel Boone Pioneer Festival when the event was held at College Park.

Fast forward over a decade later, and the two will once again take to a Winchester stage, this time at the Leeds Center for the Arts on Saturday night.

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The concert has been a long time coming and was delayed several times due to unforeseen circumstances.

“We started our band in 2018 in Nashville,” said Theo MacMillan. “By hook and by crook, and through the pandemic and different things, we have still never been able to come and play in Winchester.”

The journey back to Winchester is as much an ode to the brother and sister duo’s present as it is to their past.

“We started playing Bluegrass when I was nine, and Theo was 11,” said Brenna MacMillan. “Theo was already taking violin lessons at a young age because he was already musically inclined…Our mom and her side of the family are from Texas, and so her dad, our grandfather, sent us a little banjo and said, ‘Well, you guys live in Kentucky, so you need to play some Bluegrass,’”

Brenna would pick up the banjo, and Theo would switch from the violin to the fiddle.

The MacMillans would make a name for themselves playing around town and previously played at Leeds as part of a family band and as an opening act for the Osborne Brothers.

They continued to hone their craft through high school and college, where they were part of Berea College’s Bluegrass ensemble.

“We even did some original material for that band in school,” Theo said.

Once Theo graduated from Berea, he moved to Nashville and became heavily involved in the songwriting scene. When Brenna completed her education, she also moved south to Music City.

Reunited, the siblings decided to continue walking the path they had been on their entire lives.

“We knew that we wanted to play our songs with a Bluegrass band and also do traditional Bluegrass and progressive Bluegrass,” Theo said.

Through industry contacts, the MacMillans put together a talented band of “pickers and players.”

After five years of performing and recording the band, known as Theo & Brenna, released their first full-length album through Mountain Fever Records, “Dreams for Sale.”

The album is 12 tracks long, and the title track is a collaboration between the siblings.

“It approaches the way that we write individually and how that is different, but we put it together in one song,” Brenna said. “Spawning from that, we have eight originals on the record. Then we have a few covers on there that are spicy.”

The covers include “Be My Baby” and “I Can Hear Kentucky Calling Me.”

“’Be My Baby,’ which is the lead single, has definitely been the most successful song on the album,” Theo said. “Not many people record 60s pop songs with a Bluegrass feel to it, so it has more flare than the average Bluegrass song.”

The album is for sale on and can be purchased through most major streaming outlets.

And even with the excitement of having a new album, nothing beats the feeling of coming home.

“I cannot wait,” Theo said.

“It’s cool to come back as an adult. I don’t know how it is going to feel,” Brenna said.

To welcome the MacMillans home, purchase tickets for the 7:30 p.m. performance online at Ticket prices range from $10-$18.