That first strike of the keyboard is unmistakable. Troubles seem to melt away and for about 3 minutes, I’m in heaven — Or maybe, I just “made it to the Milky Way.”
I’ve always felt a deep connection to “Drops of Jupiter.” Millions of others must feel it too, or it wouldn’t be so iconic. Something about it captures the vastness of the universe—loneliness, love, tragedy, and peace—leaving me with a strange mix of wholeness and longing.
Heavy stuff, huh?
I recently attended my 12th Train concert. Over the years, they’ve built an impressive collection of hits—but when you’re a super fan, the hits alone aren’t enough. That night inspired me to put together my Top 20 Train songs for your next road trip—whether you’re cruising the coast, winding through the mountains, or just escaping for the day.
You’ll notice quickly that these are in no particular order — I promise you, no songs about unshaved chest hair or mermaids made this list. 🙂
Free (Train, 1998)
From their 1998 self-titled album, “Free” carries the seductive grit of Train’s early years. Its evocative lyrics paint a picture of searching for freedom—not just in the physical sense, but in emotional release and self-discovery. Lines like “They call me free—but I call me a fool” contrast outward perceptions of liberation with private doubts, balancing hope and uncertainty in a way that mirrors personal growth.
Dream On (Live cover)
If you haven’t heard Pat Monohan’s range, this is, perhaps the best example. This rendition of Steven Tyler’s “Dream on” will leave you with goose pumps. If you’re lucky enough to see it live, prepare to pick your jaw up off the floor when you hear that falsetto.
California 37 (California 37, 2012)
With its cheeky opener—“Knock, knock. Who’s there? 2012 is a brand new year” — this one hasn’t aged perfectly, but it’s pure fun. A tribute to the fans who stuck around during Train’s hiatus, it’s a fresh-start anthem with a beat that’s impossible not to sing along to.
Save Me, San Francisco (Save Me, San Francisco, 2009)
One of Train’s most joyful singalongs, this upbeat folk-pop track is a love letter to San Francisco—and to the idea of returning to a place that feels like home. Its sunny energy makes it ideal for the middle of a long drive when you need a burst of positivity.
All American Girl (My Private Nation, 2003)
This guitar-driven track brims with swagger and restless spirit. It’s an energizing choice for open highways or lively city cruising, celebrating adventure and living in the moment.
Save the Day (My Private Nation, 2003)
Bright guitars and an infectious chorus make this a feel-good anthem about being there when it counts. Play it when the sun’s out, the windows are down, and everyone’s ready for a mood boost.
My private Nation (My Private Nation, 2003)
Can you tell this album was one of my favorites? Confident and gritty, this song is about carving out your own space in the world. It’s tailor-made for long stretches of highway where you feel like the road is yours alone.
Am I Reaching You Now (For me, it’s you, 2006)
Urgent and driving, this track channels the restless energy of trying to connect before it’s too late. Best for high-energy moments when the car is buzzing with anticipation.
Shelter Me (For Me, It’s You, 2006)
A warm, gospel-tinged song about finding refuge in someone you trust. Ideal for golden-hour drives when the scenery and the mood are in sync.
For Me, It’s You (For Me, It’s You, 2006)
Yes, another self-titled album song made the favorites list. For Me, It’s You is a tender piano ballad about finding your true home in a person. Works beautifully for reflective stretches and quiet moments on the road.
50 Ways to Say Goodbye (California 37, 2012)
This theatrical breakup song turns heartbreak into hilarity with mariachi horns and over-the-top excuses. It’s pure fun and perfect for shaking off mid-drive fatigue.
Ramble On (Train does Zeppelin II, 2016)
Train’s fresh take on this classic blends nostalgia with their own style, making it a cross-generational crowd-pleaser for wide-open stretches.
Working girl (A girl, a bottle, a boat, 2017)
I’m not the biggest fan of this album in general, but something about this song strikes a chord (no pun intended). This smooth track celebrates determination and independence. Great for morning drives or when you need a motivational boost. Fans of Train’s melodic, narrative-driven songs, as well as those who enjoy artists like Sheryl Crow or Colbie Caillat, will appreciate its blend of storytelling and accessibility.
AM Gold (AM Gold, 2022)
Retro-tinged and upbeat, “AM Gold” feels like flipping on the perfect radio station during a carefree drive. Nostalgic yet fresh.
Drops of Jupiter (Drops of Jupiter, 2001)
You didn’t think I’d end this list without this one, did you? If there’s one Train song that feels destined for the open road, it’s “Drops of Jupiter.” From the first sweeping piano notes to Pat Monahan’s soaring vocals, it’s a track that manages to be both deeply personal and universally relatable. The lyrics paint a cinematic journey — part love story, part self-discovery — set against the infinite backdrop of the cosmos. It’s the kind of song that makes you want to stare out the window and let your thoughts wander far beyond the horizon.
On a road trip, “Drops of Jupiter” is more than just a song—it’s a moment. It works best during those quiet stretches when the scenery is doing all the talking, or when you’re chasing a sunset and the light hits just right. Fans of introspective ballads will love its mix of vulnerability and grandeur, while casual listeners will still get swept up in its epic, timeless feel. This isn’t just a playlist staple—it’s an anthem for dreamers and travelers alike.
Honorable mentions:
A mid-tempo blend of melodic rock and wistful reflection, “Something More” captures the desire to break free from routine and chase something deeper. It’s perfect for scenic stretches where the view sparks conversation or inspires a detour.
Borderline annoyingly cute and fun, this is a sunny, acoustic-driven ode to connection and shared moments. Best for full-on singalong mode with friends or family.
Released as the final single from their debut, “I Am” is reflective, acoustic rock that feels like a quiet conversation with yourself. Perfect for late-night drives or sunrise contemplation, it’s a reminder that sometimes the best part of travel is simply being present in the moment.
The right song can turn any stretch of road into an adventure. Load up this playlist, roll the windows down, and let Train set the rhythm for your journey. Miles go faster—and memories last longer—when the soundtrack is this good.
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