Music Travel Repeat → Backseat Benedictions: Music For A Road Trip → Vol. 6

Backseat Benedictions: Music For A Road Trip | Vol. 6 — The Ones Who Call Maryland Home

Every Friday, a growing crowd shows up for something real. Come be part of it.

Some weeks hit you harder than others. Not because of one big event, but because of the steady weight of little things—everyday burdens piling up, unspoken memories knocking around like loose change in your pocket. And when it’s one of those weeks, the only cure I know is the road.

Backseat Benedictions: Music For A Road Trip - Volume Six | Music Travel Repeat

This time, though, the road doesn’t stretch out to some faraway festival or a California coast. It bends back home. To Baltimore.

There’s something about going home when you’re worn thin. The streets are the same, the skyline still jagged against the water, but you aren’t. Every mile marker feels like a mirror asking who you are now, compared to who you were when you left.

So this playlist isn’t just another soundtrack for the road. It’s Maryland itself—an entire state stitched together in song. These are the voices that rose up from neighborhoods and basements, classrooms and clubs, the cracked corners of Annapolis bars and the shadowy warehouses of Baltimore nights.

For anyone driving home—whether it’s across town or across decades—this one’s for you.

Playlist + Reflections

1. “The Anthem” - Good Charlotte 

When you’re young, the suburbs of Waldorf can feel like a trap. That’s why Good Charlotte mattered so much—they gave kids from Maryland cul-de-sacs permission to scream back at the silence. “The Anthem” is pure gasoline. Windows down, middle fingers up, heart still racing like the first time you heard it on TRL.

This track reminds me that rebellion isn’t just for teenagers. Sometimes adults need it even more.

2. “Dear Maria, Count Me In” - All Time Low

Towson basements birthed this anthem. It’s silly, infectious, and shamelessly nostalgic. Every chorus feels like piling into a car with your friends, the kind of night where the air smells like cheap beer and freedom.

Going home doesn’t always mean facing heaviness. Sometimes it means remembering joy—and this song is the kind of joy you can belt until your throat hurts.

3.  “1-800-273-8255” - Logic w. Alessia Cara & Khalid

From Gaithersburg to the Grammy stage, Logic built a lifeline disguised as a song. This track doesn’t just live in playlists; it lives in people’s lungs, hearts, and second chances.

Driving through the Baltimore tunnels with this song playing feels like exhaling all the things you never admitted out loud. On weeks where everything feels heavy, this one gives me permission to keep going.

4. “Un-Break My Heart” - Toni Braxton

Severn raised one of the most unmistakable voices in the world. Toni Braxton doesn’t just sing heartbreak—she carves it into the air until you’re sure you’ll never forget how loss feels.

Sometimes driving home means driving past the ghosts of people you used to love, the places where you fell apart, the corners where you swore, you’d never cry again. Toni makes all of that ache holy.

5.  “Do Right” - Jimmies Chicken Shack

If you know Annapolis, you know Jimmie’s Chicken Shack. They’re the soundtrack of sticky bar floors, cheap beer bottles sweating in your hand, and long nights that felt like they could fix you if you just shouted loud enough. Fun fact: My name was strongly influenced by their lead singer, who seemed less than impressed when I told him personally at Power Plant Live! shortly before my departure. Super nice dude though! 

“Do Right” is funky, sharp, and self-aware reminding you that surviving isn’t about perfection. It’s about doing the best you can, even if that just means showing up for another week.

6. “Space Song” - Beach House

Baltimore gave the world dream-pop royalty. “Space Song” feels like staring out a rainy window in the middle of the night, headlights reflecting on wet streets, while your chest carries both hope and hurt in equal measure.

For me, this track is what Baltimore feels like after midnight. Beautiful, a little haunted, and always bigger than the sum of its cracked sidewalks.

7. “Seasons (Waiting on You)” - Future Islands 

You can’t talk about Baltimore music without talking about Samuel T. Herring pounding his chest and howling into the mic like he’s trying to wrestle life itself into submission. “Seasons” is about waiting—for love, for healing, for some kind of shift you can’t force but desperately need.

Driving home with this one feels like staring at the same skyline you grew up with, realizing you’ve changed while the city hasn’t. The waiting isn’t over, but at least you know you’re not waiting alone.

8. “Tits and Whiskey” - Mary Prankster

Raw. Sharp. Sarcastic. If Baltimore were a single song, it might sound like this. Mary Prankster could make you laugh while cutting you open with the truth hiding underneath the punchline.

There’s always something comforting about music that doesn’t pretend. It feels like walking into a dive bar back home, the kind of place where nobody’s impressed, and everyone’s just trying to survive their own week.

9. “My Girls” - Animal Collective

Weird in all the best ways. Raised in the Maryland suburbs, Animal Collective taught us that sometimes chaos is the only way to be honest. “My Girls” is messy and layered, a song about protecting the people who matter most—building shelter out of sound.

It plays like the drive down I-95 when the traffic gets unpredictable and you start questioning every route you chose. But deep down, it reminds you: it’s not about the road, it’s about who’s riding with you.

10.  “Thong Song” - Sisqo 

Look—sometimes you need depth. Sometimes you need dream-pop. And sometimes you need pure joy in its most ridiculous, unforgettable form. Baltimore gave the world this song, and whether you admit it or not, you know every word.

This is for the stretch of road when you’ve been too much in your own head, and you need a track that forces you to laugh, to sing, to let the weight drop for three minutes. Even going home needs moments of lightness.

11. “Crazy As A Good Thing” - ilyaimy

Baltimore’s ilyAIMY ( i love you And I Miss You) never played it safe, and this song proves why. “Crazy As A Good Thing” is all rhythm and conviction, acoustic fire that feels like it was written for people who’ve been told too many times to tone it down.

On the road back to Baltimore, this one feels like claiming your scars out loud. Like saying: maybe I’m crazy, but maybe that’s exactly what makes me alive. It’s the kind of track that turns a long week into fuel. It also reminds me of the day I met Heather & Rob at an open mic in Pikesville almost two decades ago. Their journal is the inspiration behind The Restless The Hopeful The Broken.

12. “Still Believe in You” - Dean Crawford

Dean Crawford’s voice carries the weight of Maryland country grit with a tenderness that sneaks up on you. “Still Believe in You” is a ballad about holding on to faith in someone, even when life makes it hard.

On the road back to Baltimore, this song feels like the ache of remembering why you loved in the first place. It’s the kind of track that makes the highway lights blur a little, not because you’re tired—but because the lyrics cut deeper than you expected.

13. “This Must Be the Place (Naïve Melody)” - David Byrne of The Talking Heads 

David Byrne grew up in Arbutus, just outside Baltimore, before changing the landscape of rock forever. “This Must Be the Place” is the kind of song that sneaks up on you—it’s not about a physical home, but about the people who make you feel like you’ve finally arrived.

For me, driving back into Baltimore, this track is the paradox: you’re returning to the streets that raised you, but realizing home might not be a zip code anymore. It might be the company you keep.

14. “Case of the Ex” - Mya

Silver Spring’s own, fierce and unapologetic. Mýa takes the mess of jealousy, betrayal, and broken promises and sings it with power instead of pity.

Heading home sometimes means passing the ghosts of old relationships—the roads you used to drive together, the diners you used to sit in at 2 a.m. This song gives you the backbone to nod at the past and keep pressing the gas.

15. “Opening” - Philip Glass

Baltimore doesn’t just give us rock and R&B—it gave us Philip Glass, one of the world’s most influential composers. “Opening” is sparse, repetitive, meditative. It feels like breathing with your ears.

On the road, this one is for the quiet stretch—late at night, highway empty, thoughts louder than the tires. Sometimes you don’t need words. Just a rhythm steady enough to remind you to keep moving.

16. “God Bless the Child” - Billie Holiday

She may have been born in Philadelphia, but Billie Holiday was raised in Baltimore, and the city never let go of her voice. “God Bless the Child” is equal parts prayer and lament, the kind of song that makes you sit up straighter even as it breaks you.

When I drive through Baltimore, I hear Billie in the air—in the cracks of old row houses, in the tired eyes of people riding the bus home late, in the resilience stitched into every block. She sang pain with such grace that it turned into strength.

17.  “Cornflake Girl” - Tori Amos

Raised in Rockville, Tori Amos carved her name with songs that cut deep. “Cornflake Girl” is surreal, playful, angry, tender—all at once.

On a road trip home, this one feels like that moment when you’re humming along to the radio and suddenly, without warning, you’re hit with a memory from years ago. The song doesn’t explain it; it just opens the door and lets the memory walk in.

18. “I Wanna Be” - John Luskey

Southern Maryland's own John Luskey has a way of writing songs that feel like they’ve been sitting in your glovebox for years, waiting for the right drive. “I Wanna Be” is equal parts yearning and grit—a declaration of wanting more, of refusing to settle for the small version of life.

On the road back to Baltimore, this one feels like rolling the windows down and saying out loud the dreams you’ve been too shy to speak. It’s a Maryland anthem of possibility, born in the kind of bars and backroads that raised us.

19. “Down” - Sweet Leda

Sweet Leda’s “Down” slides in smooth, sultry, and honest—the kind of track that wraps around you like late summer air. Julie Cymek’s voice is equal parts velvet and fire, carrying both ache and release in every note. 

On the drive back to Baltimore, “Down” feels like leaning into gravity instead of fighting it—like admitting you’re tired, you’re human, and that maybe surrender isn’t always weakness. Sometimes it’s the only way to make it home.

20.  “Happy” - Doug Segree 

An Annapolis staple, Doug Segree has always written songs that feel like conversations with a trusted friend, and “Happy” is no exception. It’s hopeful without being naïve, honest without being bitter—a reminder that joy isn’t something you stumble into, it’s something you choose, even on the hard days.

On the road back to Baltimore, this song feels like rolling the windows down and letting the week wash off you. Like choosing, mile by mile, to believe that happiness is still possible—right here, right now.

21.  “Too Old to Cry” - Voodoo Blue

Baltimore alt-rock, aching with honesty. “Too Old to Cry” sounds like the exact moment you realize that life won’t pause for your breakdowns anymore—you’ve got to keep moving, keep working, keep surviving, even when your chest is still shattered.

On the road back to Baltimore, this song feels like driving past the landmarks of your own past, recognizing the wounds they still hold, and whispering to yourself: I’m still here. I’m still standing. And maybe tears aren’t the only proof of how deep it all runs.

22. “The Therapy” - Fools & Horses

Baltimore’s Fools & Horses always had a way of making big feelings sound effortless, and “Fly Me to the Moon” is no exception. It’s soaring, sincere, and filled with that restless hope that makes you want to keep driving even when you’re almost home.

On the road back to Baltimore, this track feels like lifting your eyes off the pavement, daring to dream bigger than the week that tried to drag you down. It’s not just escape—it’s aspiration, born from Maryland heart.

23. “Bad Reputation” - Joan Jett

Raised in Rockville, Joan Jett never apologized for who she was, and that defiance carved out an entire era of music. “Bad Reputation” is a rallying cry, a refusal to play small, a promise that your truth is louder than their judgment.

Coming home with this song blaring feels like armor. Like telling the week, the critics, the ghosts: you don’t get to define me.

24. “Brother Don’t” - The Bridge

If you’ve ever seen The Bridge live in Baltimore, you know they carried the city’s soul on their backs. “Brother Don’t” is funky, heartfelt, and alive in a way that feels like family—messy, loyal, impossible to shake.

On the drive home, this one feels like forgiveness in the form of a groove. Like Baltimore whispering back: I know it’s been a week, but you’re still one of us.

25. “That Was a Crazy Game of Poker” - O.A.R

Rockville’s jam-band sons, masters of turning simple songs into endless anthems. “That Was a Crazy Game of Poker” isn’t about cards—it’s about chaos, about leaning into the mess of life and finding joy anyway.

It’s the perfect closer for a Maryland road trip playlist. Pulling into Baltimore, week still heavy on your shoulders, this one gives you permission to laugh, to shout, to roll the windows down and let the city know you’ve made it back in one piece.

Closing Reflection

Baltimore isn’t just a city—it’s a feeling.
It’s Billie’s ghost in the streetlamps, Future Islands pounding their chests on a warehouse stage, Toni Braxton’s voice reminding you that heartbreak can still be beautiful. It’s kids in Towson garages turning into All Time Low, it’s Jimmie’s Chicken Shack making Annapolis nights feel endless, it’s Logic proving that survival can be sung into existence.

And when it’s “just one of those weeks,” going home to Baltimore doesn’t fix everything—but it steadies you. Because every corner has a song, and every song has a piece of you.

So here’s your Maryland road trip. Twenty-five tracks that stretch from heartbreak to healing, chaos to calm, suburbs to city streets. Play them loud. Play them tender. Play them when the week is too much and you need a reminder that you’re not alone.

Because home isn’t perfect. But it’s yours.
And sometimes, that’s enough.

Catch you in the chaos,
Haha Bailey

Music For A Road Trip : 625 Songs & Counting!