Singer-songwriter Stephen Kellogg has never been afraid to take risks in his over 25-year career. In addition to writing honest folk-rock songs that connect with listeners, he is a natural storyteller, which has led to him giving a TEDx Talk, writing a book, and branching out into stand-up comedy.

When Kellogg launches his winter tour with a show at the Shea Theater Arts Center in Turners Falls on Thursday, Dec. 19, at 8 p.m., the one-time Valley resident will once again test some new waters by playing an all-request show. Concertgoers will get a chance to write down what they want to hear, and he’ll pull the requests out of a hat. Of course, that means he’ll be walking onstage, not knowing what he will be playing, which is risky considering he’s released 17 albums and might not remember all of his songs at that given moment.

“I have a big songbook that I will keep on stage,” he said in the event that happens. “I don’t dredge up a song from 20 years ago, but if someone asks me to play an old song, it will be exciting and thrilling and can only happen in a show like this.”

“This gives me a chance to dig into my catalog, and I hope people ask for some wild stuff,” Kellogg said in a recent phone interview. “If I mess it up, I can say ‘Well, this was your idea!’” he added with a laugh.

Kellogg says that people can request whatever they wanted, and even though he doesn’t do a lot of cover songs, he’s open to whatever might happen. “However, if someone requests ‘Bohemian Rhapsody’ there is a good likelihood that I won’t be able to do that!”

Despite having lived in the Valley and frequently performing here, this show will be the first time Kellogg has ever played in Turners Falls.

Raised in Connecticut, Kellogg came to the area in the late 1990s as a student at the University of Massachusetts Amherst. It was here that Kellogg first played in a band, but it was while living in Northampton and working at the Iron Horse that he launched his career playing to small crowds in venues like the now-defunct Fire & Water in Northampton. From the start, Kellogg’s ability to write poignant songs reflected his sense of humor and connected with audiences.

“I think that being in a community where a lot of people were making music and doing it for a living was useful to see,” he said about getting his start here. “In Northampton all these songwriters existed and were making a living. I got to see that there is an ecosystem between starving artists and household names – and that was so encouraging to see. It made me feel I can do this.”

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His brief time working at the Iron Horse, where he rotated through various jobs ranging from selling tickets to helping book shows, was also helpful in that he connected with like-minded musicians like Josh Ritter and Lori McKenna, who were also in the early stages of their careers and would become lifelong friends.

“I learned a lot there, but once I started playing gigs I knew I wanted to be on that side of it and made that transition,” he said.

Kellogg, who married his high school sweetheart, left the area in 2005 after the birth of his first daughter, and returned to Connecticut to be closer to family. His music reflects his observations of life, and he frequently writes songs about his wife and four daughters.

Many may remember Kellogg’s his time with the Sixers, the band he led and with which he released seven albums. He worked with the Sixers, who performed for the U.S. military all over the world, until they disbanded in 2012. He would forge on as a solo artist, touring with Counting Crows, playing over 2,200 shows and receiving praise from publications like Rolling Stone, which described him as “John Prine fronting the Heartbreakers.”

He’s a true survivor in a music world that has turned upside down, having endured the advent of streaming and the challenges of the pandemic. The title track of his latest album, “Keep it Up, Kid,” is an acknowledgment of his perseverance.

“The music business changed so much from what I initially signed on,” Kellogg said. “Out of the need to take care of my family, I found ways that felt more sustainable than just fighting streaming income.” And that meant being open to new things.

In 2013, the father of four conducted a successful TEDx Talk on job satisfaction that led to more speaking engagements. “What surprised me about these talks was I discovered that I loved doing this for the same reasons I love playing a show,” Kellogg said. “To connect with other people and share what I know, that is a thrill. It is about more than singing and playing guitar – it’s the storytelling and connecting with other humans.”

In 2020, he shared some of his stories in a book called “Objects In the Mirror: Thoughts On a Perfect Life From an Imperfect Person.” It’s an inspiring collection of essays that examines the most important aspects of a life well-lived.

He’s currently finishing up a new album, “To You Old Friend,” which explores friendship from different angles. Given that theme, it’s only natural that this project circles back to his time in the Valley as it features guest appearances by Lori McKenna and Dave Chalfant (The Nields). Chalfant plays bass throughout the record, which was partly recorded at his studio in Northampton.

More recently Kellogg has ventured into the world of stand-up comedy, which has become part of his show.

“For the last year I’ve been doing a show that was half stand-up comedy and half music. It’s been very fulfilling, but this Shea show is actually the first date in over a year that is not officially that,” Kellogg said. “I needed to do something a bit simpler, so it will be a mix of storytelling and music. But I am going to try and get more music in with this tour . The Shea is the test case with the ‘all request’, so we’ll see how it goes. It should be fun.”

Kellogg added that after a year of doing stand-up, there are bound to be a lot of jokes in this show.

So come to this show with your song requests and then be prepared to experience a memorable night of laughter and song.

Tickets are available at sheatheater.org or at StephenKellogg.com. This is an all-ages show. Moonrise Cartel will open.

StompBoxTrio, a group featuring Evelyn Harris of Sweet Honey in the Rock on vocals and percussion, Paul Kochanski on electric and upright bass, and John Cabán on dobro and stomp box, will grace the stage at the Wendell Full Moon Coffeehouse on Saturday, Dec. 14 at 7:30 p.m.

Harris’ powerhouse vocals, combined with her talented bandmates, makes for a sonic treat like nothing you’ve heard before. The band’s unique mix of blues, rock and soul will have people moving on the dance floor. In 2021 they released a holiday EP, so given the time of year maybe they’ll slip in a couple of seasonal tunes.

The evening will be a fundraiser for the Wendell Meetinghouse, which will support the completion and operation of this beautiful historic community meeting space.

Doors open at 7 p.m. and the show will begin with an open mic at 7:30 p.m.

Admission is cash at the door of $7 to $20, with kids under 12 for free. Bring extra cash for treats at the bake sale table.

For more information, visit www.wendellfullmoon.org.

Sheryl Hunter is a freelance writer who resides in Easthampton. Her work has appeared in various regional and national publications. She can be reached at Soundslocal@yahoo.com.