Jessi Colter to Take Waylon Jennings’ Portrait on a 49-Day Journey Around the World—A Pilgrimage of Memory and Love
Country Music

Jessi Colter to Take Waylon Jennings’ Portrait on a 49-Day Journey Around the World—A Pilgrimage of Memory and Love

Country music icon Jessi Colter has announced a poignant new chapter in her life—a 49-day journey across the globe, carrying the portrait of her late husband, Waylon Jennings. The unique pilgrimage is both a tribute to their enduring love story and a meditation on the memories they built together over decades of music, adventure, and partnership.

Speaking to the press, Jessi shared,

“Waylon always said that love and music are what keep us close to immortality. This journey isn’t just a farewell—it’s a way to relive the moments that made our life together magical, in the places where we laughed, sang, and dreamed.”


Retracing the Footsteps of Love

The journey will begin in their home in Nashville, where Waylon and Jessi wrote “Storms Never Last” on quiet afternoons.

Next stop: Austin, Texas, the city of electrifying concerts and their first youthful photographs as a couple.

From there, Jessi will travel to New York City, where the two once walked hand-in-hand through Times Square, capturing that now-iconic photo—a symbol of finding each other in the midst of chaos.

The pilgrimage then moves overseas to London, site of their first European tour and rainy afternoons sipping tea along the Thames.

Paris follows, the “city of forever promises,” where Waylon once whispered, “If you keep singing, I’ll keep loving.”

The final destination is Santa Fe, New Mexico, beneath a starlit sky—where Waylon once dreamed of resting, and Jessi will pause to say a prayer and sing beneath the stars.

At every stop, Jessi plans to sit quietly with Waylon’s portrait, light a candle, play their songs, and remember.


49 Days, 49 Letters

During these 49 days, Jessi will write 49 handwritten letters—one for each day—filled with memories, reflections, and unspoken words to Waylon. The letters will be published later this year as a memoir, “49 Nights, 49 Letters: A Journey With You,” with all proceeds benefiting the Waylon & Jessi Music Scholarship Fund.

Jessi explains,

“Not everyone gets a love big enough to last a lifetime. I want to keep ours alive—not just in memory or song, but in the hearts of anyone who’s ever believed in miracles.”


The World Responds

News of Jessi’s journey has moved millions. Artists like Willie Nelson, Kacey Musgraves, and Chris Stapleton have voiced support, calling it “a testament to loyalty and the healing power of music.”

Fans around the world are joining in, launching “Travel with Jessi & Waylon” events on social media, sharing photos, stories, and messages of encouragement.


Love Without End

Asked what she hopes to find along the way, Jessi simply smiled and said,

“No one is ever truly gone as long as someone loves them with their whole heart. I want to take Waylon with me—just as we once traveled the world together, hand in hand.”

These 49 days will close one chapter of grief and open another: a new chapter of memory, music, and love that never truly ends.

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