Winona Avenue first introduced themselves at the beginning of 2019 as a mix of alternative rock and synth pop. From Indianapolis, Indiana, Winona Avenue is a two-piece band featuring brothers Daniel Deputy and David Deputy. Inspired by 2000's pop punk and 2010's pop rock, frontman Daniel Deputy writes anthemic melodies along with purposeful lyrics. "I choose to write lyrics that are important to me and that can relate to the listener," says Daniel. "If I didn't write music that I would enjoy listening to, then what would be the point of writing? If I didn't write lyrics that can make a positive difference in the listener's life, then I'd feel as if I was doing a disservice to the listener. I believe in building others up instead of tearing others down, and music is a tool that can serve this purpose."

"We decided upon the name Winona Avenue because we grew up on a road called Winona Drive," says Daniel. "The name Winona Drive was already taken by a music production studio and we didn't want to cause any confusion, so we decided to go by the name of Winona Avenue instead." David further clarifies that "Winona Avenue can be used as a metaphor for a beginning. We all follow a route throughout our lives. Ultimately, it's the decisions we make, the way we deal with circumstances, and who we choose to follow that will determine where we will go."

In 2019, Winona Avenue released their self-titled debut album, produced by Daniel Deputy and mixed by Isaac Moreno. "I wrote over fifty different song ideas for this album. I couldn't stop writing because I wanted every song on this album to be somebody's favorite song," says Daniel. "I didn't want to just throw some halfhearted songs on the album to get it finished in a timely manner. I wanted this album to be the best material I've ever written." The band's Christian faith is established in the message of the album. "This album was written with a common theme of inspiration, optimism, life, and hope," says Daniel. "No matter the circumstances and no matter how difficult life may become, we want the listener to know that we believe God is there every step of the way and that you are capable of doing things that you may think are impossible."