Top 5 Moments of Pilgrimage Festival 2023

Pilgrimage Music & Cultural Festival returned for its ninth year this past weekend. The sold-out event, held September 23-24, featured countless performances from artists and songwriters of all genres of music playing multiple stages at The Park at Harlinsdale Farm in Franklin, Tennessee.

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In between interviewing several singer/songwriters throughout the weekend, American Songwriter caught some of the festival’s sets. Here are our top five moments of Pilgrimage Festival 2023. 

Hailey Whitters Brings the Energy and Storytelling

Hailey Whitters took the main stage on Saturday afternoon (September 23) for an energetic one-hour set that had festivalgoers singing and clapping along. The singer/songwriter performed songs throughout her catalog including fan favorites “Janice At the Hotel Bar” from her 2020 album The Dream and Top 15 single “Everything She Ain’t.”

“The thing I love about Nashville, Tennessee, and the thing I love about country music, the thing that brought me to country music was the songwriting,” Whitters said ahead of performing “Janice At the Hotel Bar.” “This next song is a storytelling song. I wrote this song, it’s based on a true story about a real woman, an 80-something-year-old woman named Janice from Jersey.”

[RELATED: Hailey Whitters on Performing at Pilgrimage Festival: “It’s High Energy”]

Set highlights included “How Far Can It Go,” which had Whitters segue into a cover of Trisha Yearwood’s “She’s In Love with the Boy,” as well as the breezy independent anthem “Tie’r Down” off her latest EP I’m In Love.

“Sometimes it takes one song to turn it all around,” Whitters confessed near the close of her set before she performed her breakthrough hit “Everything She Ain’t.” After she told the audience she’d been in Nashville chasing her dream for 16 years, she urged everyone in the audience to follow their dreams no matter how far off they might seem.

“I’ve had so many dreams come true for me,” she noted. “CMA just nominated me, little ole’ me, for Best New Country Artist. We got to go out on the road with Shania Twain and Eric Church. It’s freaking crazy. Thank you, each and every one of you, because we would not be here without y’all.” –Annie Reuter

James Bay’s Career-Spanning Set

Award-winning singer/songwriter James Bay took the Gold Record Road stage on Saturday afternoon for an energizing, career-spanning set. The 33-year-old talent kicked things off with “Best Fake Smile” from his 2015 debut album Chaos and the Calm.

“That is no kind of summer this English lad could ever handle, so respect to you,” Bay told the crowd playfully, addressing the rising temperature. He powered through the heat, treating fans to more early cuts like “If You Ever Want to Be In Love” and “Let It Go,” along with tracks like “Love Don’t Hate Me” from his 2022 album, Leap.

Festivalgoers also got a preview of Bay’s next musical chapter with two impressive new songs—the passionate “All My Broken Pieces” and his latest single, the searing heartbreak tune “Goodbye Never Felt So Bad.” – Lorie Liebig

Madeline Edwards Delivers Stellar Childish Gambino Cover

Madeline Edwards set fire to the main stage on Sunday afternoon (September 24) at Pilgrimage. Edwards’ smoky vocals never disappoint in a live setting and she kept that streak going during her set at the Franklin, Tennessee-based festival. A particularly shining moment was her cover of Childish Gambino’s “Redbone.” Edwards added a new flare to the 2016 sultry track, trading in Gambino’s staccato vocals for something looser. Elsewhere she blasted through some of her biggest tracks including fan favorites “The Wolves,” ” Mama, Dolly, Jesus,” and “Hold My Horses” from her 2022 debut album Crashlanded to great appeal. – Alex Hopper

The War and Treaty Keep Fans Singing Along

It’s hard to be in a bad mood watching The War and Treaty. The husband and wife duo of Michael and Tanya Trotter were one of the highlights of the 2023 Pilgrimage Festival. Taking the Midnight Sun stage at Harlinsdale Farm in Franklin, Tennessee, just outside of Nashville, The War and Treaty brought nonstop good energy to their set that could be heard (and felt) even from the other side of the venue.

The pair delighted the crowd with originals “Hi Ho,” “Are You Ready to Love Me?” and the title track of their 2023 album, “Lover’s Game,” along with unique covers of Otis Redding’s “(Sittin’ On) The Dock of the Bay” that led into “On the Road Again” made famous by Willie Nelson. It was clear the duo didn’t want the music to stop, as they ended the set with a five-minute outro of a lively, hard rock-meets-blues medley that included a cover of “My Girl.” They left their hearts on the stage, as the crowd remained singing even after they departed. – Cillea Houghton

Charlie Worsham Shares Songwriting Advice

During the festival, American Songwriter caught up with several artists and many of them bestowed the best songwriting advice they’ve been given. Charlie Worsham’s was memorable:

“A good habit to develop is to write every day, first thing in the morning if you can,” he tells American Songwriter. “Doesn’t have to be good. In fact, there’s a great saying, ‘Crap makes the best fertilizer.’ So, don’t be afraid to write crap. There’s something about waking up your inner songwriter, kicking ’em out of bed so they spend their day with you. If you don’t do that, that inner songwriter is going to stay in bed. When your songwriter is walking through the day with you, they’re gonna pick up all those turns of phrases that you hear, something you see, and that’s where all the great ideas come from.” – A.R.

(Photos by Erika Goldring/Getty Images)

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