I’ve always loved the way Gordon Lightfoot could make a place feel like part of the story. A highway sign, a railroad, a city left behind or a storm-tossed lake could become something larger once he put it to music.
That’s part of what makes traveling with a Gordon Lightfoot playlist so much fun. Some of the best Gordon Lightfoot songs are rooted in real places you can still visit today. So cue up the music, hit the road and follow Lightfoot from the Canadian Rockies to the Sonoran Desert and the shores of the Great Lakes.
📌 STAY UNSTOPPABLE TIP: Download a few of the best Gordon Lightfoot songs before you hit the road, then play each one as you arrive at the place that inspired it. Hearing Carefree Highway on Carefree Highway—or The Wreck of the Edmund Fitzgerald beside the Great Lakes—adds a whole new layer to the journey.
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Alberta: A Gordon Lightfoot Song Made for the Open Road
The song Alberta Bound captures that feeling travelers know so well—the excitement that builds just before a new adventure begins.
Lightfoot sings of prairie lights, Chinook winds and heading west, and I can’t think of a better song to play while packing a backpack for the Canadian Rockies. Once you arrive, Banff and Jasper National Parks offer the kind of mountain scenery that makes you want to keep driving just to see what waits around the next bend.
In my original story, I described Alberta Bound as conveying “the feeling of excitement that travellers get right before launching into a new adventure.” That feeling still fits perfectly.
RELATED: Crowsnest Pass, Alberta
Gaspé, Quebec: Following Canadian Railroad Trilogy
For railroad lovers, Canadian Railroad Trilogy is one of the best Gordon Lightfoot songs to build a trip around. The sweeping ballad tells the story of building Canada’s railroad and the laborers who swung their hammers across the country.
Follow the tracks toward Quebec’s Gaspé Peninsula, where the St. Lawrence leads into a landscape of salmon rivers, maritime villages and seaside wildlife. Or take to the tracks from the other side of the country in Vancouver.
It is easy to see why a place like this belongs in a Gordon Lightfoot song. The landscape feels big, remote and unmistakably Canadian.
📌 Recommended: 5-Day Rocky Mountaineer Train + Bus Tour: Vancouver to Calgary
Duluth, Minnesota: The Wreck of the Edmund Fitzgerald
Few songs can transport me to a place as quickly as The Wreck of the Edmund Fitzgerald. Lightfoot’s haunting telling of the freighter’s sinking made the Great Lakes feel almost mythic, and the song remains one of his most unforgettable works.
Duluth gives travelers a chance to experience Lake Superior and get a sense of the enormous scale of the Great Lakes. Stand along the waterfront watching ships move under the lift bridge, as the Edmund Fitzgerald did on its final voyage, and suddenly the geography behind the song becomes much easier to understand.
This is not just a sightseeing stop. It is a place to put the music on, look out over the water and listen.
RELATED: Why the Wreck of the Edmund Fitzgerald Still Resonates with Great Lakes Residents—50 Years Later
Savannah, Georgia: Spanish Moss
Savannah appears in Spanish Moss, and Lightfoot perfectly captures another familiar travel emotion: not wanting to leave a place you have come to love.
Travelers understand that feeling in Savannah.
Walk River Street and watch ships make their way along the Savannah River. Wander through garden-filled squares and past elegant old homes, then look up at those magnificent live oaks dripping with Spanish moss. Those were the very things I highlighted in my original story published by T+E, the Canadian travel and adventure television brand and website.
It’s the kind of city that makes you linger an extra day—and understand exactly why Lightfoot’s traveler might keep thinking about what he left behind.
One of the biggest thrills of my writing life came when Gordon Lightfoot himself tweeted a link to that original article. Then Tourism Toronto joined in, sharing the story with the comment, “Nice piece!” For a travel writer—and longtime Lightfoot fan—it was one of those pinch-me moments I’ll never forget.
Milwaukee, Wisconsin: One Gordon Lightfoot Song Leads Home
In 10 Degrees and Getting Colder, Lightfoot sings about a homesick traveler trying to hitch a ride toward Milwaukee.
That gives us a fun excuse to stop in Wisconsin’s largest city. My original recommendations included visiting the Harley-Davidson Museum, kayaking through the city on its waterways or climbing aboard a sailing ship for a trip onto Lake Michigan.
There’s something wonderfully appropriate about pairing a song about life on the road with a city where you can celebrate motorcycles, boats and just about every other way humans have figured out how to keep moving.
Boulder Dam: Another Stop in 10 Degrees and Getting Colder
That same Gordon Lightfoot song sends us much farther west.
In 10 Degrees and Getting Colder, Lightfoot’s wandering musician has also been down around Boulder Dam—the historic name associated with Hoover Dam on the Arizona-Nevada border.
For travelers, this makes a terrific addition to a Lightfoot road trip. Walk across the massive dam, peer down into Black Canyon and take in the desert landscape surrounding Lake Mead.
It’s quite a contrast to Milwaukee: one song, two places, and thousands of miles of road between them. Somehow that seems very Gordon Lightfoot.
RELATED: I Survived Kayaking the Hoover Dam
Carefree, Arizona: The Highway Sign That Became a Hit
This is my favorite connection because I heard the story directly from Gordon Lightfoot.
During a concert in Sedona, Arizona, Lightfoot told the audience how Carefree Highway got its name. He had been driving from northern Arizona toward the Phoenix airport on Interstate 17 when he noticed the highway sign for Carefree Highway.
The name stuck.
I loved hearing him tell that story because I knew the road. Suddenly an ordinary Arizona highway sign had a soundtrack.
Today, you can make the drive yourself, slipping away into the Sonoran Desert for cactus, cowboys and Southwestern scenery. Or keep going north to Sedona, where you can hike, bike or take a Jeep into those bewitching red-rock formations—the same destination I suggested in my original story.
Of all the places connected with the best Gordon Lightfoot songs, this one feels especially personal to me.
Detroit, Michigan: Two Very Different Gordon Lightfoot Stories
Detroit deserves a double stop on this road trip.
First, there is Mariners’ Church of Detroit and The Wreck of the Edmund Fitzgerald. In my original story, I recommended visiting the historic church where the bell chimed 29 times in memory of the men lost aboard the Edmund Fitzgerald.
But another Gordon Lightfoot song, Black Day in July, takes us into a much darker chapter of Detroit history. Lightfoot wrote about the violence and unrest that erupted in the city in July 1967.
Listening to these two songs while visiting Detroit reveals two very different sides of Lightfoot as a songwriter. One memorializes a maritime tragedy; the other confronts a painful moment in American history.
That ability to use a specific place to tell a much larger human story is one reason Gordon Lightfoot songs have stayed with listeners for so long.
Los Angeles, California: Early Morning Rain
There is something about airports that can make a traveler feel incredibly free—or incredibly lonely.
Early Morning Rain captures the latter.
The song has long been associated with Lightfoot watching airplanes and writing about a traveler far from home and missing someone he loves. In my original story, Los Angeles and LAX became the final stop on the journey.
And I still like the cure I suggested then: if a drizzly airport has you feeling blue, leave LAX behind and go have some fun. Head for Hollywood, the beach or Knott’s Berry Farm.
Sometimes the best remedy for a melancholy travel song is simply another adventure.
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Bonus Stop: Winnipeg, Manitoba — Where Gordon Lightfoot Played His Final Concert
Winnipeg deserves a bonus stop on this musical road trip. Gordon Lightfoot performed what would become his final concert on October 30, 2022, at the Club Regent Event Centre in Winnipeg. His set that evening included several of the best Gordon Lightfoot songs, including Sundown, Carefree Highway, If You Could Read My Mind, The Wreck of the Edmund Fitzgerald and Early Morning Rain.
That makes Manitoba’s capital an especially poignant place for Lightfoot fans to visit. While you’re in Winnipeg, explore its historic neighborhoods, riverside setting and thriving arts scene before putting on a favorite Gordon Lightfoot song and remembering that this prairie city hosted the legendary Canadian singer-songwriter’s last performance.
Take the Best Gordon Lightfoot Songs on the Road
Gordon Lightfoot had an extraordinary talent for turning geography into emotion. Mountains became anticipation. Highways became escape. Cities became memories. Lakes became places of tragedy and reverence.
That’s why traveling to the places behind the music is so much fun.
Put some of the best Gordon Lightfoot songs on your playlist, choose a destination and start driving. You may find yourself hearing a familiar song differently once you’ve stood in the place that helped inspire it.
And somewhere along the way, an ordinary highway sign might never look quite so ordinary again.
An earlier version of this story first appeared in Travel + Escape, a Canadian travel and adventure television brand and website.
Traveling soon? Don’t forget to pack these essential items
Here are 4 often-forgotten items you don’t want to leave home without:
- I would have been lost in Europe without this power bank: Anker Nano Power Bank, 10K, 45W, 8.1 oz. Just imagine your phone running out of battery while you’re exploring London.
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- You can’t beat this Sea to Summit premium neck pillow in terms of minimum weight and packed size. Who doesn’t want to get some shuteye on those long flights?
- I’m hooked on longer rain jackets that look as good on Paris boulevards as protect you on the trail.
📌 Bonus: Here’s the carry-on I swear by! My travel-tough Samsonite bags have lasted decades.
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Hi, I’m Stacey
UNSTOPPABLE Stacey Travel is a travel blog focused on immersive travel that highlights food, wine and the spirituality of place. You can count on me for accurate reports and insightful analysis as your trusted travel writer since 2008.
As the author of several spiritual and walking guides, I occasionally write about life as a Camino de Santiago pilgrim. See my Amazon author page here. You may review my credentials as a professional travel writer on LinkedIn.
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