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Caleb Stine at 49 West in Annapolis MD

49 West Coffeehouse, Winebar and Gallery
Annapolis, MD

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Date

Aug 18, 2025 7:30 PM

Admission Level	Price	Quantity
General	$17.00 ($19.51 with service fee)
Online Tickets $17 - Door $23

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Event

Name: Caleb Stine at 49 West in Annapolis MD
Start: 2025-08-18T19:30
End: 2025-08-18T21:30
Location: 49 West Coffeehouse, Winebar and Gallery

Caleb Stine at 49 West in Annapolis MD

ITZALL Goode Concerts and SHC Music Tribe Present
Caleb Stine at 49 West

Monday, August 18, 2025
49 West Coffeehouse, Winebar, and Gallery
40westcoffeehouse.com

Tickets $17 - Door $20

If you reserve an advanced ticket, do not call the venue to reserve a seat. Your ticket is your reservation. If you do not want to buy a ticket online, you can make a reservation by calling 410-626-9796

For more info, email shcmusictribe@gmail.com

ABOUT Caleb:
calebstine.com

"Calebs music has often rendered comparisons to classic folk troubadours like Townes van Zandt, Neil Young, and Kris Kristofferson. On Mystic Country, there are moments of folk, but the sound is as much influenced by jazz, rock and roll, and the blues. At times, even, I can hear the sound of the mountains, the low buzz of the wind over the plains place defines the sound as much as genre. - These Subtle Sounds

"Stine is a perfect example that the old-timey country-folk music of the past so many love can be renewed, restored, and reborn, and this is most evident on The Life and Times of a Handyman." - Music Mecca

Caleb Stine is a singer-songwriter, multi-instrumentalist, and visual artist. Though he makes his living as a folk musician, Stine wouldnt call what he does a job; he considers it a calling. His work is part-mystic poet, part-traveling preacher. As Americana UK observed, Stines upfront personality [is] seeking to make a personal connection with everyone in the venue. The albums and shows are the tip of the iceberg; to get to where he is today, Stine has put in decades of daily practice, day jobs, and deep commitment to the craft of music. Theres an element of endurance to almost everything I do, says Stine, who plays 100+ shows a year, has released 14 albums of original music, and shares a series of viral Instagram videos called Caleb Stine Says Keep Going, encouraging followers to dig deep into a creative practice of their own. Throughout his career, hes seen the music industry collapse and restructure multiple times, but its his love of music thats allowed him to outlast so many peers and institutions along the way. And its this love of music that shines through his shows, imbuing them with a communal joy that spans generations and celebrates life at its most essential.

Raised in Colorado Springs, Stine grew up in a house filled with records and books, looking out on a rocky landscape smudged with shadow and light. Both the inner and outer landscapes lent themselves to wonder, and from a young age, Stine sought a form to express it. At the age of 12, Caleb asked his mother if he could get the guitar out. She showed him the four chords she remembered from a long-ago lesson and then drove to the store. By the time she returned, with her arms full of groceries, Caleb Stine had written his first song. He continued writing and playing through high school, sharing his earliest songs at open mics and using the earnings from his job at McDonald's to buy a four-track recorder. These self-motivated efforts early on established a lifelong love of the recording process so that by the time he was making albums professionally in his twenties, hed already DIY-recorded a dozen. But to get to that point, he knew he first had to strike out on his own. It was the early influence of troubadours Bob Dylan, Woody Guthrie, and Townes Van Zandt that set Stines eyes to the horizon and filled him with longing: to make music and a life beyond the skyline of what he knew.

I hollered out at life just to see what life might bring
It brought me flowers and canyons
It brought me highways and companions
And a yearning for everything
Daniel Boone

A meandering road trip took Stine from Colorado to Baltimore, where he felt like he stumbled on a secret: a vibrant artistic community in action. He put down roots, worked on film sets by day to free up his nights for shows, and eventually formed a band called The Brakemen (the subject of 2016s documentary, It Would Not Let Me Be). From his earliest shows in 2004, hed champion Baltimore as Americas best-kept secret, and his cult-like fanbase there would champion him with the same moniker. You can have a music career, Stine says, if you spend 20 years investing in a place and its people. Stine has played almost every school, every park, and every dive bar. Hes played the Meyerhoff Symphon , the Duck Pin Bowling Alley, Campden Yards, and Andy Nelsons BBQ. Hes played weddings and funerals, kids birthday parties and cat food shop anniversaries. His shows often resemble family reunions or what people wish their family reunions felt like. Many fans attend to get a shot of humanity, to be reminded that who they are and what they do matters. Thats one of Caleb Stines strong suits. He sings Happy Birthday to fans. He takes childrens requests. He plays his hit song, Butter, and later, when someone shows up late and requests it, he plays it again. In 2009, The Baltimore Sun deemed Stine the lynchpin of the Baltimore folk scene, and in 2022, he received the Dave Giegerich Award for Excellence In The Community at the Charm City Bluegrass Festival. In return, the city has served as his creative cocoon for two decades, supporting him as hes made album after album, collaborated on project after project, exploring the outer limits of what it means to be a folk artist.

Were here Saturday to Friday country, blue, and rock and roll
We even got a record on the radio
Saturday to Friday

Ever the compulsive writer, by 2005, Stine had a batch of songs that were the best of his best. He called Clean Cuts, a local recording studio, to find an engineer up to the task. A guy just moved here from Chicago, the voice on the other end said. This sounds like his kind of project. So began Stines decades-long collaboration with engineer and producer Nick Sjostrom. Theyd go on to make countless albums together and when The Brakemens bass player, Andy Stack, went on tour with his new duo, Wye Oak Sjostrom joined the band. The result of that phone call was October 29th, recorded in a church on Stines birthday in 2005. The next record, Ill Head West Again (2008), included his first radio hit Come Back Home, a duet with Jenn Wasner (the other half of Wye Oak). That same year, Baltimores college radio station, WTMD, organized a collaboration between Stine and local rapper, Saleem Heggins. This resulted in an album, Caleb & Saleem, as well as a public art sculpture at the train museum, placement on CNN, and widespread acclaim. Stine then built his sound out for 2009s folk-rock Eyes So Strong and Clean and stripped it back for 2010s highly acclaimed I Wasnt Built For A Life Like This. 2011s Songs of Woody and Cisco was the result of his role as Cisco Houston in the Off-Broadway hit, Woody Guthrie Dreams, followed by 2012s The Fall Of The Rebel Angel, recorded with producer Travis Kitchens and printed on 100 CD copies. No matter the scope or genre of the project, a through-line remained consistent: Stines crystal clear lyricism and the depth of wisdom beyond his years. As No Depression wrote: His honest stories and thoughtful poetry place Caleb among some of the best songwriters of this time and could make him the 21st Century Townes Van Zandt.

2014 marked a line in the sand for Stine. After burning the candle at both ends touring, acting off-broadway, working in film, and living on the road, he decided that if he was going to make it as an artist, he needed to reprioritize, to make sacrifices for the art so the art wouldnt suffer. Two guiding principles led him: keep a low overhead and stay true to his artistic integrity. The result was the album Maybe God Is Lonely Too, a deep, meditative collection recorded on a four-track recorder in his row house, harkening back to the initial joy he felt in the creative process of his Colorado bedroom. From there, he buckled down on making creative decisions that felt true and exciting to him as opposed to lucrative or trendy. Whether getting mainstream recognition or not, he kept going: expanding his sound, delving into new themes, and teaming up with a rotating cast of talented friends in the Baltimore scene. For 2015s Americana-Rock Time I Let It Go, Stine collaborated again with The Brakemen Burke Sampson, EJ Thompson, and Nicholas Sjostrom. For 2018s lush concept album Moon, he handed over the role of producer to friend and fellow musician Kenny Liner. In 2019, he recorded the psychedelic Mystic Country with a new constellation of Baltimore luminaries he deemed The Revelations. In 2020, he took to the countryside to make the bluegrass-tinged Life And Times Of A Handyman alongside friends, Nicholas Sjostrom, Laur, a Kagey of The Honey Dewdro, and Audrey Hamilton. 2022s timeless Outlaw In Your Mind featured an assortment of Baltimore musicians spanning the decades, including drummer and frequent collaborator Jim Hannah. The cover photography, captured by Tim Newby, shows Stine in a fitting scene: playing guitar on a friends rooftop, the Baltimore skyline luminous behind him. Outlaw marked another line in the sand as a current-day Stine sets his sights on both Baltimore and beyond.

Stines impact has reached beyond Baltimore for years now, playing community spaces throughout the region, from Cape May, NJ, to Marylands Eastern Shore to the Shenandoah Valley. Hes brought his high-energy and heartfelt shows to the renowned stages of Delfest, Floyd Fest, and Red Wing Roots Music Festival. Hes opened for the likes of Los Lobos, Jason Isbell, and Sam Bush. Hes created soundtracks for award-winning documentaries such as Healing Neen (2009), Agave (2017), and The Body Politic (2023). But Stine is still more interested in expanding as an artist than in seeking fame or notoriety. Hes playing the long game, measuring success with a different yardstick than the one handed out by the industry. Alongside his music career, Stine maintains a daily visual art practice. Hes published five issues of his comic series, Congratulations, Youre Human, and created the artwork for many of his albums. In 2022, he was invited to exhibit a solo show of his paintings in Harrisonburg, VA, including The Road To Damascus, a 5 x 7-foot impressionist painting that took six and a half years to make. If theres one thing Stines not afraid of, its taking his time. He playfully refers to himself as The John Prine of 2029. In other words, his best years are ahead of him. They wont know about me until Im fifty, Stine jokes. And Im fine with that. In the meantime, hes going to do what he does best: keep going.

Caleb Stines album, When I Was A Cowboy, is about crossing thresholds. Stine recorded and produced the album himself while waiting for the birth of his first child. Over the ten tracks, he turns a clear eye both forward and back with depth, humor, wisdom, and poetry. Daniel Boone and Ragged and Real are fresh reworkings of previously recorded Stine songs, while No Way Out (You Aint Already Heard Of) and Cold Glass Of Water feel like they could be a hundred years old. Silver Fox celebrates a beloved mentor while providing a welcome take on aging: The older you get, he sings over a fuzzy groove, the more you do. The laid-back drive of Have Guitar, Will Travel elicits JJ Cale comparisons and highlights Stines sense of playfulness and humor. The excellently produced Cowboy, Part 1 completes the trilogy of archetypes from his previous two albums (Handyman, Outlaw, Cowboy) while the film-like Cowboy, Part 2 highlights the sensibilities that made Stine so successful at composing soundtracks. The album ends with If I Could Catch Moonlight, a love song featuring lush strings and some of Stines finest writing to date. The singer has taken on the rocky terrain of life, and the listener has traveled the sonic landscape. Both are rewarded with the love that Stine has us believing, waits for all of us on the other side.