Tyler Gregory isn’t trailblazing but he’s taking a path less traveled

T yler Gregory has never read Jack Kerouac’s novel On the Road.

But he has lived like Sal Paradise, camping out in RVs, on strangers’ couches and on apartment rooftops. “Every time I would couch-surf, I would escape in the evening up to the roof and sleep outside,” Gregory says, talking about his time wandering in New York City. “I think I slept on more rooftops than I did anything else.”

The 21 year-old Lawrence singer and songwriter looks the part of a folk troubadour with his full beard, hand-twisted leather necklaces and a feather tucked into his felt hat. But it has been a while since Gregory hit the road. “I’ve actually stuck in Lawrence for a little while,” Gregory says — two and a half years, to be exact. “It’s a small town, but there’s still so much more. I’m always drawn back to this place,” he says.

When the weather is warm, Gregory busks with his guitar on a corner on Massachusetts. Street performing and people watching inspire him. “Wintertime has been hard because a lot of my passion comes from playing on the streets,” he says. With Gregory’s deep, smoky voice and his rustic, thrumming acoustic guitar, the tunes hearken back to music traditions steeped in dust, cheap beer and working-class sorrow. His recent release, A Path Less Traveled, is a compilation of Gregory’s own experiences and a tribute to the legacy of classic ramblers such as Woody Guthrie. “The songs all have to do with traveling and stories,” Gregory says. “If you can get something across in a simple way, with simple lyrics, people can paint their own picture in their head, you know?”

Though Gregory is interested in tales of life on the road, the street player is even more interested in people’s personal narratives. He observed his fluid audiences while plucking out tunes on the sidewalks in Manhattan, Kansas, and in the subways of New York City. “Everybody is in their own little world,” he says. “What are they doing today? How are they doing? What’s their life like?” Gregory finds himself culling inspiration from Lawrence townies. “I came here so early just to watch people,” Gregory says while sipping a beer in the Eighth Street Taproom.

Born in small-town Wamego, Kansas, Gregory felt the travel itch early on. “You go to high school in Wamego, you graduate, and you go to Manhattan [Kansas] — that’s pretty much how it goes,” Gregory says. Stumbling upon a different future was an accident. “My dad had an old acoustic guitar in the attic. So, I know that sounds really cliché, but that’s how it worked. I picked up that guitar and fixed it up.” Guitar in hand, Gregory skipped classes at a tech school in Manhattan to work his way around the country, relying on friends and strangers for shelter. “I went to New York and stuff, and went around the Midwest for a while, and went to Colorado for a little bit,” Gregory says. “I stayed in a friend’s camper on the side of a mountain. The camper was a little bit tilted. There was no electricity.”

These stories and many others compose the raw, unrefined fabric of Gregory’s second album, released March 10. “I guess you could take it [the title] really literally,” he says of A Path Less Traveled. “But it’s also about experiencing things lately that I haven’t experienced in a long time. This isn’t something that I’ve ever really done with full force and passion,” he says.

Lawrence has threatened to curb Gregory’s inspiration, though. The city considered a bill that would have set up serious impediments for street performers. “A couple months ago, they proposed a ban on busking, or panhandling, I guess,” Gregory says. (The bill didn’t pass.) He blames it on the aggressive panhandlers who stroll through town during the summer. “I’m not sitting there singing, ‘Give me a dollar,'” Gregory says. Some of Lawrence’s other street musicians set up a gathering in protest. “We got some friends together and brought instruments down and went down to City Hall,” Gregory says. “That’s the life of the town,” he adds. “That’s my world.”

Gregory adores Lawrence, but wanderlust continues to tease him — “Just escaping from Lawrence and driving around and seeing old farmhouses,” he says of the need to flee civilization at times. “I remember summertime, or springtime, going out and sitting on top of a car.”

That’s one of the appeals of the Midwest for Gregory: All it takes is a few minutes to get to the middle of nowhere. “If you need to escape, you can,” he says.

Even if he’s only roaming through his music, Gregory’s songs satiate his travel urge for now. “Simple songs — they go a long way,” he says. He’s waiting to see where his straightforward melodies lead him next.