Westport native Jessica Winskell is a guitarist and musician of quiet wisdom from the Ottawa Valley whose love of music and talent for bringing songs to life have made her a welcome presence on the regional music scene. 

As a member of The Maywoods: The John Prine Experience, Jessica is part of a musical tribute to one of North America's most beloved singer-songwriters, celebrating Prine's remarkable catalogue of storytelling, humour and heartfelt songwriting. With a passion for guitar and a connection to the roots, folk and country traditions, Jessica brings her own musical personality to the stage. She will joined by the likes of up-and-comer Vicki Brittle, Tyler Craig and Nathan Sloniowski for a SOLD OUT Ontario Festival of Small Halls performance on Thursday, October 8, 2026 at the historic Cove Inn.

Seamus Cowan: If you could sit down for a private guitar lesson with any guitarist, living or dead, who would it be, and what would be the first thing you’d ask them?

Jessica Winskell: Well, first I would have to say my dad of course! He taught me and many others in the Westport area to play guitar - right in our living room. I'd also love to sit down for a lesson with Jason Isbell. I really like his style of play: blending picking and strumming, and his simple and catchy riffs that are not over the top. I would probably ask him to give me some songwriting tips too. His lyrics are so descriptive and meaningful. I have always noticed that he doesn't waste a line, there's no filler in there. Similar in that way to John Prine!

Seamus: John Prine had a remarkable gift for finding humour, heartbreak and the beauty of everyday life in his songs. What’s your favourite Prine song to play, and is there one that always gets you a little emotional?

Jessica: The crowd pleasers like In Spite of Ourselves, Spanish Pipedream, Summer's End and Sweet Revenge are always fun to play. It's so hard to pick favorites because there are so many great John Prine songs! At every show we try to add a couple new songs, but it's always so hard to remove songs from the list to make room for the new ones.

The one (of many!) that gets me emotional is probably Paradise. The thought of going back to a beautiful place you remember so fondly only to find it has been destroyed by a big corporation in the name of progress is just so sad. The line "I'm sorry my son, but you're too late in asking" gets me every time. Waiting too long to visit a place or especially a person that is special to you, and finding out one day that it's too late is so sad and something a lot of us have experienced and felt.

Seamus: Every musician has a funny or unexpected story from a gig. What’s the most memorable, bizarre or hilarious thing that’s ever happened to you on stage?

Jessica: The most memorable thing about the Maywoods shows is looking out over the crowd and seeing the audience reacting to John Prine's songs. Most people at our shows have a song that really means something to them and you can see lots of people getting emotional during the show. They laugh together, cry together, and share stories of why a particular song means so much to them. It's beautiful the way music can bring people and their experiences together and it feels magical to be a part of that experience!

Seamus: If you could travel back in time to see any musician or band perform live, at any point in their career, who would you choose, and where would you want to see them play?

Jessica: This is probably a bit obscure, but I would love to sit a few rows back at an intimate venue and see Richard and Linda Thompson when they were still together. They were a staple in my house growing up and I still love them today. My dad worked out all the chords and guitar riffs by listening to the records; my mom knew all the harmonies and wrote out all the lyrics so we could learn them. I'd love to hear them play anything from Sunnyvista, Shoot Out The Lights, I Want to See The Bright Lights Tonight.

Seamus: Your father John was a local rock star… and beloved! Hearing the stories about him gave me shivers. What are some of your favourite musical memories of your time with him?

Jessica: Something I fondly look back on is that my dad always encouraged us to be involved in jams, performances, and recording sessions no matter how old we were. When I was around 8, dad took us to a gig where his band was playing. I asked if I could come on stage, so he pulled me up, strapped a guitar on me, and his band started playing. His bandmate was calling out chords to me and I was pretending to play. I was pretty sure that I had fooled the whole crowd and his bandmates into thinking I was a pro guitar player!

Growing up, we had lots of jams and recording sessions where we were encouraged to play guitar, bass, percussion, sing, and harmonize. I would go up in our attic for hours and use his old reel-to-reel machine to write songs and layer tracks. Dad was very social and we were constantly getting together with different groups of people to make music together; it really encouraged me, inspired me, and built my love of connecting with people through music.