“Baltimore’s a colorful place — there’s a lot of characters,” said singer-songwriter Cris Jacobs in a recent phone call while trekking across the country on tour. His hometown often comes to mind when he’s writing lyrics, “when I’m kind of mining for inspiration to reflect on what’s going on around me.”

Jacobs’ fourth solo album, “One of These Days,” features two songs set against a vivid Baltimore backdrop. “Queen of the Avenue” namechecks Pigtown and Poplar Street in a narrative about post-industrial desperation in late 20th-century Baltimore, when closing factories depressed the local economy. And the celebratory “Pimlico” takes place, naturally, at the famed Baltimore racetrack.

Instead of recording these songs in Baltimore as he often has over the last two decades, however, Jacobs, 46, decided to record “One of These Days” in Nashville with a Tennessee bluegrass band, the Grammy-winning quintet the Infamous Stringdusters. But as his tour takes him back to the area Saturday with a performance at Sandy Point State Park for the Annapolis Baygrass Music Festival, Baltimore is still where Jacobs writes his songs, lives with his family and continues to foster deep connections in the local music scene.

Bluegrass was one of Jacobs’ first musical passions as he grew up in Pikesville and Owings Mills as the son of two Deadheads whose first concert was the Grateful Dead at RFK Stadium. Jacobs began gigging around Baltimore while in college in the early 2000s, playing bluegrass standards with the band Smooth Kentucky. Then he and Kenny Liner formed The Bridge, which quickly grew into something louder and more rock-oriented — Baltimore magazine even once dubbed Jacobs “The King of Rock’n’Roll.”

“When The Bridge started it was me, and Kenny, he played mandolin, and we got together picking bluegrass, just the two of us. And then we decided, yeah, it’d be cool if we just electrified this and got some drums and got weird with it,” Jacobs said.

Over four studio albums with The Bridge, his first three solo albums and “Neville Jacobs,” a 2018 collaborative album with Ivan Neville of the Neville Brothers, Jacobs has explored a wide variety of roots, rock, Americana, blues and funk. But with his first full-length leap into the Appalachian melodies and distinctive instrumentation of bluegrass on the “One of These Days” album, Jacobs surrounded himself with the best possible help, including Jerry Douglas, a bluegrass legend who’s worked with everyone from Eric Clapton to Garth Brooks.

“When I had the whole spark for the idea, I called Jerry Douglas to see if he’d produce it, and then called the Stringdusters, because they’re good friends of mine, to see if they’d be willing to play on it.” Jacobs took a brief pause with a self-deprecating laugh. “And then I had to write the songs.”

Those songs, written in the barn next to Jacobs’ house over the next four months, fit comfortably into the hallowed bluegrass tradition while acutely expressing what was going on in the songwriter’s life. “Daughter, Daughter” is a touching reflection on fatherhood, while “Cold, Cold Walls” is a meditation on mortality. In fact, actual transcendental meditation is one of the new habits Jacobs picked up to get through the difficult last few years that inspired the poignant lyrics throughout “One of These Days.”

“I had met Cris at a festival called Delfest,” said Douglas via email, recalling that he was instantly impressed by Jacobs’ musicianship. “Cris and his band played just before my band. He instantly grabbed my attention playing his slide cigar box guitar, then moving from song to song with ease and dynamically working the crowd into a frenzy. I had to follow that, so I remember digging in a little extra that day.”

An impressive array of musicians turned up to help Jacobs on the album. Billy Strings, perhaps the biggest star on the progressive bluegrass scene these days, plays guitar on “Poor Davey.” Veteran country hitmaker Lee Ann Womack harmonizes with Jacobs on “Work Song (I Can Still Sing).” New Grass Revival mandolinist Sam Bush, a two-time inductee into the International Bluegrass Music Hall of Fame, appears on multiple songs on the album, as does the gospel trio the McCrary Sisters.

Those collaborations came about organically, as Jacobs spent a week recording at the Sound Emporium in Nashville, occasionally making calls around town to see who could help a song reach its full potential. “I had Jerry Douglas producing the record, so he’s got a pretty nice Rolodex,” Jacobs said. “But it was all natural, it wasn’t like, ‘Let’s make a star-studded record so that I can say that it’s star-studded.’ ”

“The guest collaborations came after we had the songs dressed. We had a good look at them then started casting,” Douglas explained. “I held ‘Lifetime To Go’ for Lee Ann Womack. She is a world-class singer of singers. Then in came Billy Strings to blow the doors off of ‘Poor Davey.’ One of the best times I’ve had in the studio.”

From 2001 to 2011, The Bridge built up a loyal local fanbase and toured nationally, playing several major festivals. They won Best Band in Baltimore City Paper’s 2005 readers’ poll, with their debut “Cross Street Market” winning Best Album as well. The band’s eclectic sound and freewheeling improvisational tangents earned The Bridge a following on the “jam band” circuit, though Jacobs has mixed feelings about that categorization.

“It’s not that we didn’t want to be called that. It’s just, you know, there’s connotations to that word and it’s such a big umbrella of styles that it may have hurt us at times, it may have helped us at times,” he said. “We liked to write actual songs, and lyrics were sort of the central focus. And then in live shows, we were into the jamming.”

Jacobs still plays the occasional Bridge song in his concerts, but he also found it creatively liberating to go solo. “I was in a band with those guys for 10 years and they’re my best friends and I love them all to death. But maybe there was a little bit of like, ‘All right, I’m just going to do anything I want to do right now and nobody can tell me not to, and we’ll see how it goes.’ ”

For many years, The Bridge maintained an annual tradition of a hometown Thanksgiving Eve show. On Nov. 27, the band will reunite one more time for a show at the Recher in Towson that’s been billed as “The Final Feast.”

Ahead of that, he’ll spend this weekend performing in Maryland’s capital, where some of his “One of These Days” collaborators, the Infamous Stringdusters and Sam Bush, are also on the bill. As he spends the next couple months touring throughout the U.S. and even playing a date in Portugal, he’ll still be representing his hometown wherever he goes.

“I take pride in being sort of an ambassador of Baltimore in the music world,” Jacobs said.