49 West - Coffeehouse, Winebar & Gallery / Annapolis, Maryland

Future Country, Josh Mudge, Katie May & Derek Torsani
2025-08-09 19:30 - 22:00 (America/New_York)
Please call for your reservations at 410-626-9796

Sinners
2025-08-10 16:00 - 18:00 (America/New_York) | 49 West – The Front Room, 49 West St., Annapolis, MD, 21401, United States
Sinners – where Hippie Happy Hour meets Classical Happy Hour! This group of Maryland musicians, assembled by Emil Petruncio, includes Emil on keyboard and vocals, Diana McFadden on cello, Pam Godfrey on flute, Joe Klausner on mandolin, fiddle, and banjo, Mark Ingino on guitar, and Carolyn Krohn and Ren Rick on vocals. Join us for redemptive renditions of tunes from Bob Dylan, John Prine, Garcia and Hunter, Simon and Garfunkel, and other masters of Americana music!

Tim Kurtzberg
2025-08-10 18:00 - 21:00 (America/New_York)

Leslie Webber
2025-08-11 17:00 - 19:00 (America/New_York) | 49 West – The Front Room, 49 West St., Annapolis, MD, 21401, United States
Please join us for Happy Hour with Leslie Webber playing up front 5-7pm

2nd Monday Songwriters Showcase
2025-08-11 19:30 - 22:30 (America/New_York)
Screenshot
August 11 info: Angie Miller hosting with Mark St. Pierre on percussion and special guests Burnsie, Meg McDermott, and David Augustus

Seth Mitchell & Friends
2025-08-12 19:30 - 21:30 (America/New_York)
PLEASE CALL FOR YOUR RESERVATIONS AT 410-626-9796.
The Seth Mitchell Band pairs vibrant bluegrass sensibilities with award-winning originals, covers drawn from a wide range of influences, and the best of the bluegrass canon. Since its inception in 2023 and following the release of Seth Mitchell’s Glen Burnie Man album, in 2024, the band has emerged as one of the most dynamic songwriter-led bands in the regional scene.

Special Event- The Dave Chappell Band
2025-08-13 17:00 - 19:00 (America/New_York)

Songbird Collective
2025-08-13 19:30 - 22:00 (America/New_York)

The Annapolis Round Up
2025-08-14 19:30 - 22:30 (America/New_York)

Noah Teague Booz
2025-08-15 19:30 - 22:30 (America/New_York)
Frankie McCabe, Gwen, & Josh Mudge

John Jensen
2025-08-16 16:00 - 18:00, 2025-08-23 16:00 - 18:00, 2025-08-30 16:00 - 18:00 (America/Halifax)

American Roots Night with Gary Wright & Leah Weiss
2025-08-16 19:30 - 22:30 (America/New_York)

The Befuddlers
2025-08-17 16:00 - 18:00 (America/New_York)

Dream Punch
2025-08-17 19:30 - 21:30 (America/New_York)

ITZALL Goode Concerts and SHC Music Tribe Present Caleb Stine at 49 West
2025-08-18 19:30 - 22:30 (America/New_York)
Monday, August 18, 2025
ITZALL Goode Concerts and SHC Music Tribe Present
Caleb Stine at 49 West
Tickets $17 – Door $20
https://calebstineat49.bpt.me
You can buy a ticket in advance or make a reservation by calling 410-626-9796. Do not do both. You can also walk in, provided seats are available.
For more info, email shcmusictribe@gmail.com
ABOUT Caleb:
calebstine.com
We Will Endure: https://www.youtube.com/watch?v=EeECzZ7EALI
“Caleb’s 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 wouldn’t call what he does a job; he considers it a calling. His work is part-mystic poet, part-traveling preacher. As Americana UK observed, “Stine’s 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. “There’s 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, he’s seen the music industry collapse and restructure multiple times, but it’s his love of music that’s allowed him to outlast so many peers and institutions along the way. And it’s 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, he’d 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 Stine’s eyes to the horizon and filled him with longing: to make music – and a life – beyond the skyline of what he knew.
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 2016’s documentary, “It Would Not Let Me Be”). From his earliest shows in 2004, he’d champion Baltimore as America’s 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. He’s played the Meyerhoff Symphon , the Duck Pin Bowling Alley, Campden Yards, and Andy Nelson’s BBQ. He’s 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. That’s one of Caleb Stine’s strong suits. He sings Happy Birthday to fans. He takes children’s 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 he’s made album after album, collaborated on project after project, exploring the outer limits of what it means to be a folk artist.
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 Stine’s decades-long collaboration with engineer and producer Nick Sjostrom. They’d go on to make countless albums together and – when The Brakemen’s 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 Stine’s birthday in 2005. The next record, I’ll 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, Baltimore’s 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 2009’s folk-rock Eyes So Strong and Clean and stripped it back for 2010’s highly acclaimed I Wasn’t Built For A Life Like This. 2011’s Songs of Woody and Cisco was the result of his role as Cisco Houston in the Off-Broadway hit, “Woody Guthrie Dreams,” followed by 2012’s 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: Stine’s 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 wouldn’t 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 2015’s Americana-Rock Time I Let It Go, Stine collaborated again with The Brakemen – Burke Sampson, EJ Thompson, and Nicholas Sjostrom. For 2018’s 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. 2022’s 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 friend’s 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.
Stine’s impact has reached beyond Baltimore for years now, playing community spaces throughout the region, from Cape May, NJ, to Maryland’s Eastern Shore to the Shenandoah Valley. He’s brought his high-energy and heartfelt shows to the renowned stages of Delfest, Floyd Fest, and Red Wing Roots Music Festival. He’s opened for the likes of Los Lobos, Jason Isbell, and Sam Bush. He’s 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. He’s 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. He’s published five issues of his comic series, “Congratulations, You’re 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 there’s one thing Stine’s not afraid of, it’s 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 won’t know about me until I’m fifty,” Stine jokes. “And I’m fine with that.” In the meantime, he’s going to do what he does best: keep going.
Caleb Stine’s 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 Ain’t 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” evokes comparisons to JJ Cale and highlights Stine’s 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 Stine’s 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.

Unified Jazz Ensemble
2025-08-19 19:00 - 21:30 UTC | 49 West – The Back Room, 49 West St., Annapolis, MD, 21401, United States
Playing the 1st, 3rd (and sometimes) the 5th Tuesdays of the Month!
The Unified Jazz Ensemble is a dynamic group of masterful musicians from the USA. This ensemble has years of experience educating and entertaining diverse audiences. This is acoustic jazz, a classic American art form, done to perfection with audience interaction at its best.

Dave Chappell & Friends- AKA HippieHappy Hour
2025-08-20 17:00 - 19:00, 2025-08-27 17:00 - 19:00 UTC | 49 West – The Back Room, 49 West St., Annapolis, MD, 21401, United States
Dave Chappell, Jimmy Jacobs, Rurik Reshetiloff & more!

Not Your Mothers Paint Night
2025-08-20 19:45 - 22:30 (America/New_York)

Jazz Wire Jam Session
2025-08-21 19:30 - 22:30 (America/Halifax)
Jeff Antoniuk’s Monthly JazzWire Jam Session
7:30 pm – 10:30 pm ($10 cover)
One of the top jazz jam sessions in the DC/MD/VA area is right here at 49 West! Hosted by jazz education legend Jeff Antoniuk, and sponsored by JazzWire (www.JazzWire.net), this is friendly, welcoming and swinging good time. Adult amateurs and semi-pros, high school students and hot shot college players all converge on the 3rd Thursday of the month to share their stuff.
The first set (7:30pm) features one of Jeff Antoniuk’s Jazz Band Masterclass (www.JazzBandMasterclass.com) groups in concert. From 8:30pm on, they are the house band for the jam session. Come one, come all, and tell your friends. There isn’t a more fun night out this month! Cover $10

Justin Trawick & Mark Farmer
2025-08-22 20:00 - 22:30 (America/New_York)

AJ & The Lovecats
2025-08-23 19:30 - 22:30 (America/New_York)

Rehaashed- Wilco
2025-08-25 19:30 - 22:30 (America/New_York)

Hot Funyuns
2025-08-26 19:30 - 22:30 (America/New_York)

Mr VCR & Friends
2025-08-27 20:00 - 22:00 (America/New_York)

Cafe Scientifique
2025-08-28 18:00 - 19:15 (America/New_York)
Thursday, August 28, 2025, 6:00 – 7:15pm
Title of Talk: Conserving Maryland’s Farmland Raptors
Speaker: Alex Pellegrini, Farmland Raptor Program Coordinator, Maryland Bird Conservation Partnership
About the Talk: The Maryland Bird Conservation Partnership’s Farmland Raptor Program is dedicated to advancing our understanding and conservation of raptors associated with grassland and farmland habitats across Maryland. The program focuses on four priority species: American Kestrel, Northern Harrier, American Barn Owl, and Short-eared Owl. In this talk, Alex Pellegrini will highlight his research on Barn Owls and Short-eared Owls, exploring their fascinating life histories and the challenges they face. He’ll also discuss ongoing local and global efforts to protect these declining species and what’s being done to secure their future in Maryland’s working landscapes.
About the Speaker: Alex Pellegrini is the Farmland Raptor Program Coordinator with the Maryland Bird Conservation Partnership. In this role, he manages statewide nest box programs and leads several research initiatives focused on grassland raptor conservation. His work also includes collaborations with the Global Owl Project, the Global Short-eared Owl Working Group, and Project Owlnet, contributing to research on owl taxonomy and migration.

The Jonathan Epley Guitar Trio
2025-08-28 19:30 - 23:00 (America/Halifax)

Sound of…Presents: Last Summer With Evan Sky Scott of the Andes Elsie Colette Noelle Acaso
2025-08-29 19:30 - 22:30 (America/New_York)
Sound of…Presents: Last Summer
With
Evan Sky
Scott of the Andes
Elsie Colette
Noelle Acaso
$15
Doors: 7:30
Show: 8:00
