SHOW REVIEW: Notes From The 2025 Annapolis Songwriters Festival
Originally Published on Americana Highways
Notes From The 2025 Annapolis Songwriters Festival:
A Haimish Haven for True Listening
Annapolis isn’t the sort of town where you usually see folks with guitar cases on the sidewalk. For most of the year, pink polo shirts far outnumber black T-shirts, and you’ll spot twenty pairs of topsiders for every pair of boots. But for one weekend each year—when the Annapolis Songwriters Festival rolls into town—that balance flips.
The festival runs for four days, and this year I was only able to attend two of them. There are always multiple shows (often 6–7) going on at the same time, so even those who are at the festival for the full duration will miss much more than they will hear. It is an interesting feeling to experience fear of missing out while sitting in one show and thinking about the show next door! I cannot claim to offer a comprehensive review, but I hope these notes provide a snapshot of a great event.
The Spirit of the Festival
There’s a great Yiddish word that perfectly captures the festival’s atmosphere—haimish. Like most great Yiddish words, it’s hard to translate directly: it means comfortable, homey, warm, and unpretentious. Picture a table full of performers’ relatives, grandparents at the head, introducing themselves to everyone around them. Everyone feels like family, not strangers—a perfect fit for a weekend devoted to listening and shared music.
At one show, a band even paused mid-set to check in for a Southwest flight—exactly twenty-four hours, of course, before departure—lest they end up in the dreaded “C Group.”
Songs That Linger
A songwriter’s festival is, first and foremost, about songs. Great songs, songs that stay with you long after the show has ended, are rare and precious. This year’s gathering delivered more than a few standouts:
“I Don’t Bring My Guitar to Nashville Anymore” – Ray Weaver, a heartfelt story of a songwriter who never quite made it in Nashville.
“Cul-de-Sac Kid” – Jess Jocoy, exploring what it means to bring a suburban voice to country music: “Do I still get to talk if the way I talk isn’t picked-up southern drawl?”
“It Runs Deep” – Garrett Boys’ powerful mission statement about their rootsy music and the history it is inspired by.
Road Songs, Travel Themes, and Trains
Classic songwriter motifs ran strongly through the weekend. Road songs and train songs were everywhere, giving the festival a sense of movement and story:
Steve Lowe’s “Jump Right In” and “Sounds from Old Towns” beautifully captured the restless pull of the highway.
The Garret Boys’ “On a Train” offered a playful, meta twist on the classic train song.
Songs about the open road, travel, and life in motion threaded through performances by Gage Rhodes, Aaron Raitiere, and others.
These pieces reminded listeners that much of Americana songwriting thrives in transit—songs that carry you down a highway, past landscapes, or through the lives of those on the move.
New Voices, New Work
Many artists arrived with fresh material, sometimes reading lyrics straight from their phones:
Gage Rhodes – “Clawin’,” a poignant reflection on a changing Eastern Shore: “This place used to feel like something.”
Aaron Raitiere – “Truck Buddies,” a simple but fun song based on the fact that “Truck” rhymes with another word which is often paired with “buddies.”
David Tolliver – “I Bury the Dead for a Living,” delivered with haunting simplicity: “I’m just somebody nobody sees.”
Hidden Gems and Hitmakers
The festival balanced emerging voices with proven hit writers:
Aaron Raitiere co-wrote “You Look Like You Love Me,” Ella Langley and Riley Green’s 2025 ACM Single of the Year.
Jeff Middleton co-wrote Jason Aldean and Miranda Lambert’s 2018 Country Airplay No. 1 “Drowns the Whiskey.”
Raitiere performed in the unofficial uniform of men preforming at songwriter festivals—backwards baseball cap and black tee—sharing a crowd favorite about choosing fishing over church: “I’d rather be on a lake with my mind on God in the middle of his creation than in church with my mind on fishing.”
Sonia Leigh matched him with road-song authenticity in “Sweet Annie,” the Zac Brown Band’s 2013 Country Airplay chart-topper that she co-wrote with members of the Zac Brown band. “I’ve been burning bright for so long I can’t remember; pretty girls and late-night bars seem to be my line of work.”
The Gift of Listening
Artist after artist welcomed the crowd’s focus. One performer compared playing in bars to a friend sharing their deepest secret: “and you spit in their face—that’s how it feels when an audience doesn’t listen.” Here, every word mattered, and attentive silence became part of the art.
Humor, Conscience, and Heartbreak
There was plenty of humor too. Chris Nurthen grinned through lines like: “You can keep your suit and jacket, keep your stability, I’ll trust in my ability,” and the sweetly romantic: “Your kisses still taste like royal honey, even when there’s a lot of month left at the end of the money.”
Songs of conscience emerged as well, perhaps not as many as one might expect. Ray Weaver offered a number of powerful, political songs, including “The Blood Is Never on Their Hands,” which warns: “Men in the shadows of high places send out their heartless commands; they never live with the consequences, the blood is never on their hands.”
Heartbreak had its say too. John Haywood’s perfectly crafted line, “She found her happily ever after—after me,” lingered long after the set ended. Tia Sellers, one of the few wielding an electric guitar, delivered a tune about goodbyes, “You’re In My Marrow Now.” David Tolliver’s “I Hope You Have a Beautiful Life” and Danah Denice’s “To Say Goodbye” added to the weekend’s exquisitely crafted heartbreak.
There was something almost perverse about hearing such heavy songs on a bright Annapolis afternoon. Many belonged in smoky bars—if any still exist. Yet in the sunshine, with a crowd leaning in, these songs found a comfortable home.
A Perfect Fit
The Annapolis Songwriters Festival turned the city into a haimish haven—a space where songs could breathe, and where true listening became the headline act. You can learn more about these artists, and all the artists I was not able to see, on the festival’s website. And it’s not too soon to save the date for next year’s festival – September 10-13, 2026.