Bourbon Legend’s Ultimate Road Trip Playlist Guide: Songs to Fuel Your Journey

There’s nothing quite like a good road trip. The open road, the wind rushing through the windows, the mix of excitement and freedom—it's all made better by the perfect soundtrack. Whether you’re cruising solo, rolling deep with friends, or heading to a gig with your band, music is the ultimate travel companion.

We asked each member of Bourbon Legend to share five songs that they’d put on their ultimate road trip playlist. What we got was a mix of rock anthems, sentimental favorites, and a few wild cards—each list telling its own story of adventure and nostalgia.

Megan’s Road Trip Wild Card Mix

Megan believes a good road trip playlist depends entirely on who’s in the car. For this hypothetical trip with Bourbon Legend, she’d craft a setlist that introduces new favorites, builds energy, and ends with a surprise twist:

• Gomez – "Get Miles" (Setting the vibe)

• The Silver Spear/Ducks on the Mill Pond (Turning up the energy)

• Matchbox 20 – "How Far We’ve Come" (A band singalong moment)

• Mike Posner & The Futuristics – "Turn Up" (A sentimental pause)

• Thot Squad – ""Pound Cake (A left turn to "ruin the vibe")

Megan’s philosophy: A road trip playlist should start with something relevant, build momentum, include singalongs, create bonding moments, and then, just when everyone’s comfortable—throw a curveball.

David’s Road Trip Playlist Rules

David, a seasoned road tripper, found it impossible to narrow his list to just five songs. Instead, he came up with five essential rules for the perfect playlist:

1. Something that makes you smile.

2. Something that makes you think.

3. Something that lets your mind wander.

4. Something you can sing along to.

5. Something you can dance to.

His takeaway? If your playlist checks these boxes, you’re in for an unforgettable ride.

Matt’s High-Octane Mix

For Matt, the perfect road trip song makes you want to downshift, set cruise control, pull a J-turn, scream out the window, and feel like the world is ending and perfect at the same time. His selections pull from high school road trip staples like Eve 6, Foo Fighters, and Tool, while his college days leaned into Coheed and The Mars Volta.

Jim’s Album-Oriented Approach

Jim prefers to let full albums play out, creating a vibe that evolves with the drive. His picks reflect that long-haul listening style:

• The Allman Brothers Band – "Blue Sky" (from Eat a Peach)

• Lynyrd Skynyrd – "Free Bird" (from One More from the Road) (Watch your speedometer on this one.)

• Guns N’ Roses – "Welcome to the Jungle" (from Appetite for Destruction)

• Aerosmith – "Back in the Saddle" (from Rocks)

• Anything he's currently obsessed with that he can belt out with the windows down.

  
  

Bill’s Feel-Good Road Trip Classics

Bill’s list focuses on the feel of the music. Whether it’s a song you can sing along to, a beat that makes you tap the steering wheel, or a riff that makes you roll down the windows, the right road trip song is all about the moment.

• Lynyrd Skynyrd – "Free Bird"

• Pearl Jam – "Even Flow"

• Led Zeppelin – "Ramble On"

• Kings of Leon – "King of the Rodeo"

• Ice Cube – "It Was a Good Day"

His philosophy? A good mix needs variety—something with a singalong chorus, a killer beat, and a song that just lets you feel the drive.

What Makes the Perfect Road Trip Playlist?

If there’s one takeaway from Bourbon Legend’s picks, it’s this: the best road trip songs aren’t just about the music—they’re about the moment. Whether you’re blasting classics, discovering new favorites, or just letting an album ride, the key is to create an experience that matches the adventure.

Now, we want to hear from you! What’s on your ultimate road trip playlist? Drop a comment and let us know!