Home Live Review Live Review: Annapolis Songwriters Festival @ Annapolis, MD — 9/10-9/13/26

Live Review: Annapolis Songwriters Festival @ Annapolis, MD — 9/10-9/13/26

September 22, 2026

Judy Blank and Kristen McNamara perform live during Annapolis Songwriters Festival at Rams Head On Stage on Sept. 11, 2026. (Photo by Steve Satzberg)

Annapolis Songwriters Festival: Of Magic Potions and Superpowers
Words by Liz Wyatt
Photos by Steve Satzberg

For four talent-packed days, the Annapolis Songwriters Festival filled the historic streets, bars, restaurants, and music venues of downtown Annapolis with giants — and not just Young the Giant.

From Sept. 10-13, songwriters from around the country converged on Maryland’s capital for performances stretching from late morning well into the night at venues including 49 West, Rams Head On Stage, The Garden on Market Space, Blackwall Hitch, Stan and Joe’s Saloon, Galway Bay, and the festival’s large Calvert Street stage.

These were national songwriting treasures, hitmakers, Grammy nominees, and award winners whose collective résumés could fill a data center. Instead of attempting to document them all, I offer the CliffsNotes version of the tome at hand: what it felt like to wander around Naptown among these giants, often from 11am until 2am, for four days.

Our adventure began in the back room at 49 West, where David Sparrow offered love songs while Davonne D’Neil countered with jazzy soul and funk, including a lively, bluesy performance that carried echoes of Ella Fitzgerald’s clear, buoyant scat singing.

At Rams Head On Stage, Judy Blank sang in an intimate, narrative, almost self-conversational style. Her soft vocals brought a little garden to life, while her guitar could be so delicate that the performance felt almost a cappella. Her vibe was Dorothy meets Punky Brewster — delightfully authentic and naturally joyful.

Taking turns with Blank was Gloria Anderson, who sang with powerful vocals and introduced the first song she wrote at age 15: “Leaves change color and blow away.” She later increased the tempo with strong, pulsing guitar and a sultry, bluesy, no-nonsense delivery, tossing out lines including, “Ha, ha, you’re living in your momma’s basement,” and, “Oh no, you did not.”

All the righteous anger of a woman scorned rolled through the octaves Anderson poured over us.

At The Garden on Market Space, Shelby Morgan brought a vintage flavor, some Pat Benatar flair, and a touch of ’90s pop. She was joined by self-taught Madisun Bailey, whose soul, jazz, and funk made me wonder, “Did I hear an echo of Erykah Badu?”

Both are Annapolis treasures.

Bailey performed “Magic Potion,” and what a sweet universe Madisun Bailey creates. She bends the laws of physics, somehow sounding as though there are two guitars and a bass player inside her fingers, then finding room for percussive trills that only she knows how she is making.

Magic potion, indeed.

Watch Madisun Bailey perform live for Sanity Lounge on YouTube:

At Blackwall Hitch, Drumming Bird stopped me with the question, “What’s your reason for living? Will you replace it with me?”

Then, at Stan and Joe’s Saloon, Justin Wilson sang, “I’ve been sober since you broke my heart in two.”

Tears caught the whole saloon.

He would not have mercy on us. On and on came the heartache. Chris Cagle picked up the next song with, “Thank God she left the whiskey.”

After Wilson’s performance at Stan and Joe’s, I started following him around the festival. As if his high notes and pain-inducing wail were not impressive enough, this seasoned songwriter cranked his guitar up a half-step and wailed it out again.

Then another half-step.

The afternoon crowd at Stan and Joe’s went wild.

Then came another half-step. And another.

By the time Wilson was finished, I was blubbering. When I caught him on his way out afterward, he gave poor little me a laugh-filled hug.

What a superpower.

Elsewhere, songwriter Tia Sillers performed “I Hope You Dance,” the Lee Ann Womack hit she co-wrote with Mark D. Sanders. Sillers told the audience the song had saved her life and was a gift from God.

Watch Tia Sillers perform “I Hope You Dance” live for 30A Songwriters Festival 2025 on YouTube:

Alex Amen treated us to some hillbilly-picking guitar before Anthony David arrived with “Cold Turkey,” perhaps the yummiest song I heard all weekend. I immediately made a note to see him again.

Amen was full of witty, playful banter. He said he has a place in New York that he never stays in, but a friend of his loves it very much.

His tender picking and loving lyrics, delivered in an equally gentle voice, lulled Rams Head On Stage into silence.

The next day, I found Anthony David at 49 West.

I immediately went full Horshack: “Oh! Oh! Oh! Can you play ‘Cold Turkey’ again?”

“For the lady in the back,” David responded.

Mind you, 49 West is a very intimate venue. There really isn’t much of a “back.”

So there I was, an early-morning woo girl for this Grammy-nominated magic man.

David sang “Out of My League,” and announced that he would be at Galway Bay at 8pm.

I wrote that down.

He then led us through a mellow, delicious singalong. Our part was, “I gotta girlfriend,” as he sang about how difficult some people can be to resist.

We made a pretty good choir for Mr. David.

That is another thing this festival demonstrated: Annapolis knows how to appreciate music. There is no better audience than a Naptown audience.

Nashville, eat your heart out.

Back at 49 West, Austin Sawyer of Drumming Bird triggered more tears with the line, “When you love someone, you tell them they are enough.”

Sawyer also brought thoughtful, irreverent, wise-beyond-his-years banter to the room. And 49 West itself is a jewel of Annapolis, with actual artwork hanging seemingly everywhere.

Two inches below where my shoulder touched the wall was a $1,200 painting that I kept knocking. So did my tablemate, who also happened to be the sound guy. The painting became a 2-inch teeter-totter between us.

There was abundance and beauty in the air, and practically dripping off the walls.

Watch Drumming Bird perform “American Spirits” live at The Mountain Opry on YouTube:

Later in the festival, the big outdoor stage showcased local songwriter Danah Denice, who walked out in a hot-pink tie-dye halter and bell-bottoms looking every bit the star.

A spectacular presence, Denice also is the founder of Songbird Collective, designed as an outlet for the songs of abuse survivors.

Pure star quality.

From there, I drifted toward the Rams Head patio, hoping to find something — anything — resembling a seat.

I eventually squeezed myself beside a bush, practically in the mulch of a flower bed, to hear Madisun Bailey and Brad Hutsell.

Hutsell’s popping country had heads bobbing, feet bouncing, and the whole crowd wriggling in its seats. Bailey sang “Knocking” while the cicadas roared in the background, seemingly determined to provide their own backing vocals.

When Bailey stopped playing, there was a little jolt — like stepping off an escalator and suddenly having to remember that the ground no longer moves beneath you.

All of Annapolis seemed alive and singing: every cicada, every sweat bee, every lanternfly buzzing along in the same flow and harmony.

But I still had that 8pm date with Galway Bay.

Going there meant missing Young the Giant on the large Calvert Street stage. Instead, I wandered down to one of Annapolis’ hidden gems and nestled myself into what little breathing room remained at Galway Bay.

I found a spot near the doorway, only feet from Justin Wilson.

Even through his sunglasses, I could tell he was smiling at me, waiting for the tears he now knew he could summon on command.

Then, lo and behold, Anthony David strolled in and lingered in that same doorway while David Ryan Harris joined the songwriters gathered inside.

Naturally, I geeked out.

I told Anthony that to my ears, he sounded like Seal, D’Angelo, and India.Arie — as if all three somehow had a musical baby.

He laughed and pointed out that he was older than they were. He also told me he had written two India.Arie songs.

That stopped me in my tracks.

Here I was, standing in the doorway of an Irish pub in Annapolis, talking to a songwriter whose music was connected to the very sound I had been trying to describe.

That was the festival in miniature.

I was constantly in awe of the caliber of artists simply floating through the streets, restaurants, bars, and tiny rooms of Naptown all weekend.

So, no, I did not see Young the Giant.

I was nestled instead in the loving bosom of Galway Bay, fraternizing with giants of another kind.

After experiencing the Annapolis Songwriters Festival from roughly 11am until 2am, day after day, Annapolis began to feel like one enormous living room. We were all dorm mates passing one another in the common areas.

You kept seeing the same audience members. You kept geeking out with the same people. You kept bumping into the performers themselves.

Eventually, even nationally known, Grammy-honored songwriters began to feel less like distant figures on a stage and more like fellow travelers sharing the city for a weekend.

And that may be what makes the Annapolis Songwriters Festival so special.

It isn’t really about stages or backstage passes. It is about real people, real songs, and the writers who have filled our airwaves and touched our lives for years — sometimes without most of us ever knowing their names.

For four days, they filled downtown Annapolis instead.

They sang in theaters. They squeezed into bars. They wandered the streets. They listened to one another. They talked to us.

And suddenly, the people behind the songs were right there in the room.

Don’t let next year’s festival pass without spending at least a day or two wandering Naptown among the giants.

Well done, Annapolis.

Here are some photos of songwriters performing across the Annapolis Songwriters Festival 2026. All pictures copyright and courtesy of Steve Satzberg.

Alexander Peters