In the Country with Dave Woods:
Kendall Lily

This month the spotlight is on Stouffville, Ontario’s Kendall Lily.

Welcome to the Spotlight, Kendall! Take us back to the time when you realized you wanted to be a country artist. What inspired you to start that journey?

Hello Dave! Thank you so much for having me!

I have always loved singing and growing up my mum always listened to country music in the car. As much as I loved to sing, I had really terrible stage fright. It was so bad that when I got up to sing for an audience for the first time, as the song was starting, I shook my head and ran out! After we left, I was so disappointed that I didn’t even try and vowed to myself that I would never run out again, and that I would keep trying. Eventually, I became really comfortable on stages, and it still feels like such a privilege to share music with people when it was something I was once so afraid to do. I’m not sure there was one specific moment where I realized I wanted to be a country artist. I think it was something that crept on me the more I worked at it. With every audience I played for, stage I stepped onto, song I wrote, it all just made me fall in love with country music even more.

Who are some of the artists who have influenced you & why?

There are so many artists that have influenced me, but some of my favourites are Avery Anna, Carrie Underwood and Ella Langley. I love that Avery Anna’s songs don’t all sound the same, and that she is really experimenting within the country umbrella (country-pop, country-rock, etc.). What I love about Carrie Underwood is her powerful emotional vocals and the way she can tell a story. I’ve been listening to her since I was little. And lastly, Ella Langley has been on repeat lately! I love her authenticity and her songwriting. I’m also inspired by how all of these artists share their faith.

What have you’ve learned about writing songs since your first started writing?

When I first started writing songs I was fourteen, coming out of the pandemic, and just starting high school. I immediately fell in love with songwriting as an outlet, and taking a negative feeling and turning into something positive. Since then, I’ve begun using songwriting as a medium for telling my stories, in hopes people see a little bit of their own. My songwriting has grown up with me, and I have learned to always write from an honest, vulnerable place.

What do you think country music does better than other genres?

What I love most about country music through the decades is the deep storytelling. Country music always seems to have a way of telling a relatable story in a way that is real, and accessible. I think it has a special way of making people feel seen, and telling a story that is emotional but easy to listen to. I also think country music has really fostered a sense of community that other genres haven’t. I love attending other artists’ shows, and I have been so encouraged by others as well.

Are there any parts of a music career that you find challenging? And how have you handled those challenges?

I think one part of a music career that I find difficult is taking the songs I wrote with just my voice and my acoustic guitar, and changing them into fully produced pieces. Like I said, I love writing and have a whole catalogue of songs. These songs are so close to my heart, but when you’re collaborating with others, you have to release it a little bit. Not that you can’t have a say or articulate your vision, but rather allow others to offer their opinions, be open to new ideas, and overall let people help make it come to life. I think working with the right people has helped me face this challenge, and just continuing to push forward, knowing that getting to share my music live has been so special, I just can’t wait to share my music in this way too.

Who would be your ultimate duet partner choice and why?

This is always such a tough question because how can you possibly decide! First of all, I am so inspired by all the Canadian country artists I’ve met as I’ve been performing. They are all so unique, talented and supportive. I am always streaming their music in case they ever need a duet partner! In general though, I would love to sing with Avery Anna, Ella Langley, or Emily Ann Roberts! Obviously they are all incredibly talented, but they also just seem really genuine and sweet, and sometimes part of clicking musically is clicking personally!

What are you looking forward to & hoping to accomplish in your music career over the next year?

I am really excited to be releasing my first single “For Good” this Fall! It is a song that is close to my heart, and one that is about saying goodbye to someone for the last time. I’m going to be recording and releasing more music in the next year, and of course performing as much as I can.

Check out Kendall on her socials! You’ll find the links here: https://www.liinks.co/kendall.lily

Dave Woods is a monthly columnist for CMAOntario and hosts the popular podcast & social media page In The Country with Dave Woods and he runs various songwriters showcases including Country Nights In The City at The Moonshine Cafe in Oakville, the Heart Of Country Songwriters Showcase at the Rec Room in Mississauga as well as Back To My Roots at The Painted Lady in Toronto – plus more! In 2023 & 2024, Dave was named the CMAOntario Industry Person Of The Year & was nominated in 2025 & 2026. He was named Best Local Promoter at the Mississauga Music Awards in 2025 & 2026.