The other day, a woman approached singer-songwriter Jordan Smart while he was playing his guitar at Lovers Point. It was the fifth anniversary of her husband’s death and she was spreading his ashes in the accepting ocean.


“She slipped me something and said she was inspired by my music,” Smart says. “I didn’t realize it at first but when she left, I discovered she gave me a $100 bill.”


Smart – performing Friday at Pierce Ranch with openers Cast Iron Keith and the Stainless Steel Band – lives for those kinds of experiences, not because of the cash, but because of the opportunity to connect with strangers on a deeper level.


The 23-year-old left his home state of Ohio a few years back and took to the road to explore the world and, on occasion, settle down briefly in places like Pueblo, Colo., and here in Monterey. While all the interactions on the road aroused creativity, Smart has also dealt with the hard realities of being broke and having nowhere to crash.


“I’ve slept under bridges by myself, hitchhiked alone and didn’t know if I was going to eat that night,” he says. “I’ve definitely seen a lot of darkness.”


Tunes like “Truth” – a descendent of Dylan’s traveling, honky tonk-flavored “Freight Train Blues” – highlight the musician’s ability to paint an honest, and not necessarily positive, portrait of his life.


“Where’d all my money go? I thought I still had a dime,” Smart sings in a voice that sounds like a homeless John Mayer.


The young vagabond says his travels are far from over. A permanent residence isn’t in his near future.


“It’s a dream I have in the future to settle down somewhere,” Smart says, “but for now, I like the idea of going everywhere I can and seeing everything I can to inspire future songs. I’m back in Monterey until I leave again.” 


JORDAN SMART and CAST IRON KEITH and the STAINLESS STEEL BAND perform at 8:30pm Friday, June 1, at Pierce Ranch Tasting Room, 499 Wave St., Monterey. $5. 372-8900.