Although Jessica Lynn Calamera grew up in Westchester, she is a country girl at heart.
The Yorktown Heights singer, songwriter and musician, who goes simply by the name Jessica Lynn, has spent the last year touring the country, but she will be returning to her home county on Saturday to perform alongside 12 other artists at the Pleasantville Music Festival.
“Traveling across the country was so much fun, and you meet so many cool and exciting people, but coming home just feels amazing,” she said. “You get to see your friends and family and also just get to show everybody how hard we’ve worked on the show since we’ve been away.”
A 2008 Lakeland High School graduate, Jessica Lynn has been performing since childhood, having taken piano lessons and then teaching herself how to play guitar and drums as she grew older. She said that music always came naturally to her, which should come as no surprise, since both of her parents are musicians as well.
Jessica Lynn decided to take her family on the road with her. Her father, Peter, plays bass in her band while her mother, Victoria, is a backup vocalist.
“There’s a whole different level of trust and comfort there and it just makes things easier — having people that are so close to you and know you so well with you all the time and that you know have your best interest in mind all the time,” she said.
Her boyfriend, Steve Sterlacci, is also a member of the band, playing lead guitar. She said her relationship with Sterlacci, which began three-and-a-half years ago, served as inspiration for several of the songs on her latest album, “This Much Fun.”
Jessica Lynn writes all of her own songs, which are largely based on events in her life. She joked that if you put the songs from her new album in a certain order, it becomes sort of a musical biography. But she noted that being able to connect with fans through personal stories is one of the most rewarding aspects of her career.
During a recent performance of her song “Pretty,” which speaks about the difficulties many young women face trying to live up to societal perceptions of beauty, she recalled a girl who started crying.
“That’s what means so much to you, writing your own stuff, because your story can touch somebody else in that way and you have that connection with them that’s just not possible through any other medium but music,” Jessica Lynn said.
Although a Westchester native, Jessica Lynn won’t be staying put for long. She recently signed a contract that will take her to Nashville to write music alongside some of the biggest names in the industry, including songwriters who have written material for Aerosmith and Carrie Underwood. She hopes that this opportunity will jumpstart her goal of securing a record deal and becoming a household name.
Of course, she is already on her way to achieving that goal with a PBS special, “This Much Fun—Live at the Winery at St. George,” that has been airing across the country since May. The special, which was filmed two years ago at the Mohegan Lake winery, gives her an opportunity to share her music with people outside the area. A second special will be filmed at the Paramount in Peekskill in September.
Perhaps Jessica Lynn’s proudest career moments so far was when she was twic invited to sing the National Anthem at Madison Square Garden, once prior to a basketball game, the other before a bull-riding competition.
“I was always so nervous to sing the National Anthem, in high school or [at] any local things,” she said. “I never auditioned to sing it, all throughout growing up, because I was always afraid of not doing it justice, so my very, very first time singing the National Anthem was at Madison Square Garden. What a way to start.”
Jessica Lynn is scheduled to appear on the festival’s Main Stage at 2 p.m. For more information, including a complete list of performers at the Pleasantville Music Festival, visit www.pleasantvillemusicfestival.com.