Who knew there were so many cowboys around coastal Maine?

In truth, I’d had an idea. Saturday night’s State Theater appearance by Charley Crockett, one of the hottest – and most unique – artists in country music, had been sold out many months in advance. I’d secured tickets when they went on sale back in January, and my wife and I then proceeded with plans to host a Portland early-summer weekend built around the show for four of our closest friends, arriving in from Pennsylvania and New Jersey. Among other things, the long lead time gave our group ample time to get their all-important Western-wear outfits together.

What it is that makes Crockett so unique is a bit difficult to summarize. I’ll give it a try: he plays modern country music that sounds totally old-fashioned. Or is it that he takes almost musty, old-west stylings and bestows them with a sophisticated, present-day sheen? Alternately, that his razor-sharp production, instrumentation and presentation feel like it might suitably be accompanied by a tumbleweed blowing past a swinging saloon door?

Roughly 24 hours before Crockett was to hit the stage, we began to hit the town. Starting with some malty house-made whiskies at Maine Craft Distilling (they were prepping to begin their part of Portland’s 2nd annual Feel Good Funk Fest) and moving on to dinner at the Old Port headliner Scales – for both menu and setting, still my favorite restaurant in town after close to 10 visits (the breads alone make it worth your while).

Saturday/showday began with a casual stroll along serene Crescent Beach and continued with a midday roof-deck nosh back home facilitated by passes through Washington Ave.’s Cheese Shop of Portland and Commercial Street’s Browne Trading Market (oy, the cost of lobster meat these days). Later, another exceptional meal, this time at Thistle & Grouse, an outstanding newcomer to Portland’s crowded, elite restaurant scene, where the manager was nice enough to play some Crockett tunes during the dinner hour.

Finally our group arrived at the corner of Congress and High Streets, at Portland’s historic and charmingly vibey State Theater. Double-fisted IPAs, pilsners and margaritas in hand, we staked out our space on the crowded but never uncomfortable GA floor, awaiting the appearance of the new-generation country traditionalist who’d brought us all together.


Crockett, who just turned 40, has not necessarily lived the typical cowboy life. Born in San Benito, Texas, tucked in at the southern tip of the Lonestar state mere miles from the Mexican border, he spent formative time in Dallas, New Orleans, New York City, northern California, Paris and briefly in Spain and Morocco. At 17, he bought a guitar at a pawn shop and taught himself how to play. “I started to write songs immediately, without any chord knowledge or anything,” Crockett recounted. “I didn’t know what key I was in for 12 years. But my ear was good.”

The State show started auspiciously with “$10 Cowboy,” the instantly catchy title-track off Crockett’s just-released new album, his 13th in a prolific recording career still under a decade long. This immediately set into motion a completely captivating 26-song set list which blended honky-tonk, some soulful R&B and even blues numbers, along with a few revealing covers (the Waylon Jennings/Willie Nelson combo “Good Hearted Woman” was a particular favorite of our crowd), into the time-traveling country-western showcase Crockett proved uniquely qualified to deliver.

Crockett is the real deal. Peering out from beneath his oddly high-perched cowboy hat, his dark, deep-set eyes give you the idea that he’s seen some stuff. With a plaintive delivery through a clipped Texan drawl, he manages the precarious sonic feat of feeling both retro and contemporary.

We arose Sunday morning for a two-hour Sail Portland boat charter, breezing past Pumpkin Knob Island, Pocahontas Light (as we learned, the smallest lighthouse registered with the U.S. Coast Guard at just six-feet tall), and the many Casco Bay highlights, while enjoying literal smooth sailing aboard the Eleanor Hawkes. The eventful Crockett-themed weekend wrapped up with scotch eggs and juicy lamb burgers at pleasantly just-off-the-beaten-path King’s Head Pub.

In between, there was time to further contemplate a proper identifier for Crockett’s vintage approach. One thing for certain is that Crockett’s traditional sound is most definitely not a product churned out of the now-dominant, arguably soulless, Nashville pop-country machine. After attending the last of Crockett’s recent run of three sold-out shows in London, none other than Jimmy Page – yes, that Jimmy Page – said of him: “I hadn’t seen anything quite like it for a very long time! I was blown away by the depth of his songs, his musicianship and communication with the audience. Charley is a performer in the true cowboy tradition. He’s a troubadour.”

Troubadour. I think Jimmy is on to something.

Comments are no longer available on this story