Long before the US tourism industry officially began to use music as a cultural touchstone to attract tourists, the sounds of the American South inspired me to make a pilgrimage to legendary musical meccas Memphis, Mississippi and Louisiana to immerse myself in some of the iconic sounds that populated my record collection and were the foundations of the formative rock music that I loved both then and now.

Not Country mind you, but Roots, Bluegrass, Dixieland, Cajun, Zydeco, and especially Blues. Dubbed the “Blues Pilgrimage,” my nearly two-week journey in 1994 also served as a last-gasp bachelor fling with two buddies a month before I was to walk down the aisle and such road trips were destined to be replaced by family trips to Niagara Falls and Florida.

Heading out from Toronto, our ultimate destination was New Orleans, with many purposefully chosen stops along the way – not least being the Mississippi Delta, home of the Blues. On our trip, we stopped at Elvis’s birthplace, discovered that the legendary “Crossroads” was inexplicably being marketed as “Home of the Big Frog,” found my happy place at Preservation Hall, and learned the Cajun Two-Step with the help of some mature yet nimble grandmotherly types in a dance hall in Houma, Louisiana.

The trip was everything we expected, and a few things we didn’t, but it was undeniably epic.

Fast forward 25 years – a perfect number that lends itself to reflection and anniversaries – and the idea began to germinate to reprise the trip, not least because for years my music-obsessed son, rather than asking “Are we there yet?” from the backseat of the car, had harassed me with the refrain, “When are you taking me to New Orleans?” – and not for the Bourbon Street party scene (he doesn’t drink), but for the city’s iconic musical stature.

Perhaps it’s because I had serenaded baby Brendan with tunes by city legend Fats Domino – “Ain’t That A Shame,” “Blueberry Hill,” etc. – that he got the music into his blood, or that he later gravitated towards the guitar, teaching himself to play the Blues (particularly BB King and Muddy Waters), but I was somehow blessed with a kid who not only mirrored my tastes in music but quite strikingly shunned what most others his age listen to.

In truth, Brendan wanted to wait until he turned 21 to make pilgrimages to New Orleans (and Chicago) so that he would be of legal age in the US to enter the bars and clubs where the music is played.

So, when the synergy of his long-held passion (coupled with reaching the age of majority) and my lingering nostalgia at last intersected, “Blues Pilgrimage 2” was born: for him, a themed exploration of the southern US through the prism of the music he loves, paired with an innate sense of civil rights and cultural injustice (which helped fuel Blues music) and, not to be discounted, a culinary quest befitting a young man with an outsized and equally adventurous appetite; for me, it was the unique and amazing opportunity to reprise a trip I did just before marriage with one of the results of that union, and, from a professional perspective, to see what had changed. (And to see if Buckwheat Zydeco had made it onto Spotify – he has!)

Brendan and I were veteran road-trippers (we have watched whales and eaten poutine in Quebec and called in Cleveland for the Rock and Roll Hall of Fame), but this was different, the (ful)filling of a cherished bucket list entry. He trusted me entirely with the planning – in fact, he didn’t want to know, preferring to revel in the anticipation of the journey and ensuring that no surprise would be shattered. I must say, I took great delight in arranging things I knew he would die for: calling at the BB King museum in Indianola, Mississippi; chowing down on a food tour and prowling Frenchman Street in search of music in New Orleans; dodging gators on a swamp tour and spending a night at a plantation in rural Louisiana; grooving to Swamp Pop in Houma, and taking in the Tabasco Factory near Lafayette, La.

Despite a limited knowledge of our itinerary at the outset, Brendan was well prepared. He had a list of all the towns his blues favourites had been born or lived in as we followed the Blues Highway in Mississippi. And the music! His carefully curated playlist for the car included Johnny Cash and bluegrass in Nashville, Mark Cohn (“Walking in Memphis”) in Memphis, blues and gospel selections in Mississippi (including playing artists in their home towns), Lucinda (Williams) in Lafayette, Lynyrd Skynyrd in “sweet home” Alabama, and an assortment of Cajun and Zydeco masters throughout Bayou Country in Louisiana.

We also had time to marvel that we thought we saw a man with a confederate flag T-shirt at the site of the Lorraine Hotel (where MLK was assassinated) in Memphis – photo evidence later showed it was the Norwegian flag; oops!, but a good conversation nonetheless – and ponder such mysteries as how it is that Mississippi Fred McDowell actually came from Tennessee. And why Clarksdale, Mississippi – the epicentre of the Blues – had hung its hat on that big frog thing when I had visited in the ‘90s.

With such distractions, our 22 hours on the road (each way) seemed considerably shorter. After all, we had ample time to bond over BB, get enthused over Elvis, have fun with Fats, and, in between, delve the depths of mutual favourites like Steve Earle, John Hyatt, Robert Earl Keen, and the Avett Brothers. Not to mention, enough Blues to last even me for another 25 years.

Then again, Brendan is already planning. “I know what I’m doing in 25 years,” he informed me somewhere along the way. I’m pretty sure he doesn’t mean with me, but hopefully I’ll be available just in case.

Either way, the circle, I’m confident to believe, will continue to be unbroken.

(Stay tuned for part 2 of this column, which will break down the destinations and highlights of our southern exposure, and some changes I found 25 years down the road.)