A Holiday Tradition That Hits All the Right Notes
The holidays wouldn’t feel complete without all of your favorite Christmas music blasting. Few events give you the chance to hear your favorites sung on stage quite like the annual Annapolis Christmas Show, presented by Annapolis Musicians Fund for Musicians (AMFM) and hosted at Rams Head On Stage.
This beloved annual tradition, in its 27th year, brought together local artists, original songs, and classic Christmas favorites for two nights of festive performances on Monday, December 15, and Tuesday, December 16, all in support of Annapolis’ music community.
AMFM, a nonprofit founded in 2006, provides emergency financial relief to professional Annapolis musicians who are unable to work due to illness, injury, or other unforeseen circumstances. Over the years, the organization has expanded its mission to include catastrophic relief and youth music support through scholarships and private lessons—making this concert not just entertaining, but deeply meaningful.
We attended Monday night’s show, and from the moment the music started, it was clear why this event has been going strong for 27 years. Check out some of our highlights from the show!
Brass, Spoons, and Bourbon Street Energy
Each night kicked off with the Naptown Brass Band, who instantly transformed the room with high-energy, New Orleans–style flair. Their sound made it feel less like a seated concert and more like a stroll down Bourbon Street. It was joyful, loud, and impossible not to tap your toes. An unexpected personal obsession of mine came courtesy of the band’s percussionist playing spoons against a washboard (an instrument I later researched is called a frottoir). New life goal unlocked: learn to play one in 2026.
Original Songs and Crowd-Pleasing Classics
Another highlight was Doug Segree, who performed an original holiday tune titled “Mr. Santa Claus,” followed by a spirited rendition of “Rockin’ Around the Christmas Tree,” complete with a full band. His performance struck that perfect balance between heartfelt and fun, exactly what a holiday concert should deliver.
A Charlie Brown Moment (and a Full Heart)
One of the most touching moments of the night came from Dana Biagini, who brought his young son George onstage to play piano during their performance of “Christmas Time Is Here” from A Charlie Brown Christmas. Watching George play (with the poise and feel of a tiny Vince Guaraldi) was nothing short of amazing. It was sweet, sincere, and had the entire room smiling. My heart grew at least three sizes.
Performance of the Night
My favorite performance belonged to Madisun Bailey. She took the stage with a stripped-down, soulful rendition of “Blue Christmas” that immediately quieted the room. Madisun’s voice carried every ounce of longing and vulnerability the song requires.
She then invited members of the Songbird Collective* to join her onstage for “Happy Xmas (War Is Over),” sharing that she wanted to wish everyone a holiday filled with peace and love. With the rich harmonies of the Songbirds layered over the familiar melody, and with the chaos of the world over the past year, and even the weight of recent news still fresh, it was a genuinely moving moment. The performance felt hopeful without being naïve, tender without being overproduced, and deeply human. It was beautiful in the way live music can be at its very best.
Music That Gives Back
What makes the AMFM Christmas Show so special is that it’s not just a concert, it’s a reminder that community matters. AMFM helps support the musicians who bring life, energy, and joy to Annapolis all year long. I left the show feeling festive and grateful for our awesome city and community.
Keep the Music Going at Rams Head On Stage
If you’re ready for some live entertainment like this, Rams Head On Stage has a stacked lineup coming up:
- 12/19 – Paula Poundstone
- 12/20 – A SQRRL! Holiday (matinee)
- 12/20 – Low Cut Connie with Kendra Morris
- 12/21 – Happy Holidays Drag Brunch
- 12/21 – Jon McLaughlin & Friends: Home For The Holidays with T.3
- 12/23 – The Dirty Grass Players with The Black-Eyed Suzies
- 12/26 – Jimmie’s Chicken Shack Holidaze Show
- 12/27 & 12/28 – Pressing Strings
- 12/29 – Stephen Kellogg’s Old Friends Tour featuring The Kellogg Sisters
- 12/30 – The Seldom Scene
- 12/31 – The New Romance: The Ultimate 80s Prom NYE Dance Party
If you’re looking for a reason to get out, support artists, or soak up some holiday cheer, Rams Head has you covered.
*The Songbird Collective supports women and non-binary artists through mentorship, networking, artist development, performance opportunities, and events like Songbird Festival. They are committed to creating a safe, equitable space for musicians to grow—free from toxic industry norms like sexism, harassment, and unequal pay.
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