LEO SUNDAY Singer/songwriter/storyteller Leo Sunday & Friends performing Inside Out - a journey of truth, hope, and resilience—living life from the inside out
October 19, 2025 @ 2:00PM — 4:00PM Eastern Time (US & Canada) Add to Calendar
The Buttonwood Tree Performing Arts Center: 605 Main St Middletown, CT 06457 Get Directions
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LEO SUNDAY Singer/songwriter/storyteller Leo Sunday & Friends performing Inside Out - a journey of truth, hope, and resilience—living life from the inside out
Singer/Songwriter/Storyteller Leo Sunday has been delighting audiences for decades with his unique brand of Americana, pop, jazz, country, folk and acoustic rock music. He performs regularly throughout the US as a solo performer, entertainer, guitarist, keyboardist, vocalist, and freelance trumpet artist.
As an independent recording artist, Leo has put out several CD’s, EP’s and Live Album Projects and is currently working on his latest project, “Inside Out” - a collection of Country, Roots, Bluegrass and Americana music written during Leo Sunday’s travels around the South and Southwestern US since the Pandemic! Look for a release in June of 2026.
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Event Description
Leo Sunday and Friends will be debuting all unreleased original songs from a June1 2026 release of the Double Vinyl Album - Inside Out
Inside Out
“A journey of truth, hope, and resilience—living life from the inside out.” Words & Music by Leo Sunday (Lavallee)
Inside Out is a tapestry of stories that honor the grit, hope, honesty, and love it takes to truly live. From wrestling with regret and the weight of what we didn’t know, to choosing love over fear, and finding joy even in hardship, these songs walk through the mess and beauty of being human. They remind us that living from the inside out means embracing our stories with courage, letting our colors unfurl, and choosing, again and again, to lead with love.
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This concert and other Buttonwood Tree events brought to you by our generous donors and patrons, and the following community organizations: