The Lesser-Known Truth Of Taylor Swift's Childhood And Hometown

Dimitrios Kambouris/Getty Images

Born in 1989 in West Reading, Pennsylvania, singer-songwriter Taylor Swift is, at this point, a worldwide phenomenon. However, even though Taylor entered the music industry at a very early age, details of her childhood aren't very widely known.

Her parents are Andrea Swift, a marketing-executive-turned-homemaker, and Scott Swift, a former Merrill Lynch stockbroker who was later appointed as the vice president of the company. Andrea gave birth to Taylor's brother Austin in 1992, and the couple raised their two children in Pennsylvania — initially in West Reading and then in Wyomissing.

Over her years in the limelight, the country singer, who was named after famous musician James Taylor, has revealed a lot about the time she spent in Pennsylvania, and so have Pennsylvanians who knew her as a child. Here are a few anecdotes from Taylor's childhood that are sure to amuse all Swifties (and non-Swifties for that matter) out there.

Back in 2019, when Taylor Swift released her now fan favorite Christmas song, "Christmas Tree Farm," she took to Instagram to share a photo of her younger self holding a dog on a Christmas tree farm and wrote in the caption, "I actually did grow up on a Christmas tree farm. In a gingerbread house, deep within the yummy gummy gumdrop forest," she playfully wrote. As it turns out, her words weren't completely untrue. The singer's family did, in fact, own and live on a Christmas tree farm in West Reading, Pennsylvania, during her formative years.

Speaking to Esquire in 2014, Swift elaborated on how her father managed the farm while working a corporate job and how she helped in its daily operations. She noted, "[My father would] tend to the farm as his hobby. He'd get up four hours early to go mow the fields on his tractor. We all had jobs. Mine was picking the praying-mantis pods off of the trees, collecting them so that the bugs wouldn't hatch inside people's houses ... The only reason that was my job was because I was too little to help lift trees." Swift also told the outlet that the farm is the reason behind her "unnatural level of excitement about fall and then the holiday season."

Taylor Swift started on her path to being educated at West Reading's Alvernia Montessori School, where she spent her preschool and kindergarten years. Her parents then enrolled her in The Wyndcroft School in Pottstown, Pennsylvania. As the saying goes, the cream always rises to the top. The fact that Swift and her talent didn't go unnoticed even when she was a child reflects well in what the singer's childhood teachers have said about her.

Barbara Kolvek, a former music teacher who coached a very young Swift for four consecutive years at The Wyndcroft School, told CBS News, "She always was writing poetry, always. Even in music class, even when she shouldn't ... I feel like maybe I gave her a little spark or encouragement to do what she was doing." The news outlet also spoke to Heather Brown, who was Swift's teacher at the school when she was a third grader. Brown noted, "Every student has a special quality. And you always remember every student from the quality they have. Taylor's quality was just being she was one of those students where people just drew to."

Back when Taylor Swift was nine, her family relocated to Wyomissing, Pennsylvania, where she attended Wyomissing Area Junior/Senior High School. At the time, Swift frequented New York City for vocal and acting classes as well as Broadway auditions. Expressing her love for acting on stage in a 2012 interview with Inquirer.net, Swift noted, "I actually started out in theater. When I was growing up in Pennsylvania, auditioning for Broadway was my dream. I went to several auditions in New York. I was always going there for vocal and acting lessons ... After a few years of auditioning in New York and not getting anything, I started writing songs. But I never lost my love for theater."

In February 2024, actor, comedian, and Swift's long-time friend Tobin Mitnick took to Instagram to share childhood photos of Swift and himself acting on stage as Sandy and Danny from "Grease," respectively. The caption of his post read, "Thank you mom for digging these pics of @taylorswift and I harmonizing like buttah on summer nights twenty five years ago out of storage," indicating Swift was about nine when the photos were taken. Apart from "Grease," a nine-year-old Swift also acted in plays like "Bye Bye Birdie," "Annie," and "The Sound of Music" for Berks Youth Theatre Academy.

Kevin Mazur/Getty Images

Taylor Swift, who, as previously mentioned, started taking acting classes as a nine-year-old, didn't take much time to realize what she wanted to do in life. She was only 10 when she figured out what her purpose was and decided she'd make a name for herself in the country music scene. Swift developed a passion for country music as a young child, thanks to artists like Dolly Parton and Patsy Cline, whose songs became staples for her when it came to participating in local events and music competitions during her childhood years.

As Swift revealed in an interview with The Independent back in 2013, singers Shania Twain and Faith Hill have also had a deep impact on her as a child, helping her lay the groundwork for shaping her career path. She said, "Shania Twain ... was just so strong and so independent and wrote all her songs. That meant so much to me. She is one of the most successful female artists to ever hit country music and I was inspired by her. I also saw a VH1 Special on country singer Faith Hill and I was sure that country music was what I wanted to do. After watching that TV program I was obsessively, obnoxiously bugging my parents every day about it until finally we planned a trip to Nashville."

Michael Loccisano/Getty Images

At the age of 11, Taylor Swift ultimately managed to persuade her mother to take her to Nashville so that she could visit record labels and ask for a break. Speaking to CMT in 2008, the singer recalled what her first trip to Nashville was like. She said, "It was on spring break, and I was 11 and I had this little demo CD — a karaoke CD of me singing songs by Dolly Parton and the Dixie Chicks and LeAnn Rimes. And I marched up and down Music Row with these demo CDs, and I'd walk in and hand them to the receptionist while my mom and my little brother were parked outside in a rental car."

Although the trip wasn't exactly fruitful, it helped Swift in two different ways: it left her without regrets about trying and made her realize what she actually needed to earn herself a record deal. Swift pledged to return to Nashville with qualities other singers looking for a break in the city didn't possess. As she put it, "I had figured out the whole performing and singing thing. I just realized I needed something else. So I went back to Pennsylvania and started writing songs and playing guitar."

Jason Squires/Getty Images

On multiple occasions, Taylor Swift has spoken about how a local computer repairman and musician visiting the Swifts' Wyomissing house to fix their computer offered her his guidance on a few guitar chords when she was 12. However, Swift's account of the story is pretty different from that of the computer repairman in question, Ronnie Cremer. According to Cremer, Swift's parents asked him to be Swift's guitar teacher, and he took the job long before he was asked to fix their computer. However, in 2015, Cremer became one of the many people Swift has threatened to sue so far.

In January 2015, Cremer, who claims to have given Swift guitar lessons for two long years, launched a website called itaughttaylorswift.com. According to the Daily News, shortly after the website's launch, Swift's legal team threatened to sue Cremer, asking him to take it down with an email that read, in part, "[Your domain name] incorporates the famous Taylor Swift trademark in its entirety and suggests [Swift's rights management company's] sponsorship or endorsement of your website." At the time, Cremer told the said outlet that he also "got a lot of hate mail from Swift fans who just do not want to believe under any circumstances that Taylor lied to them." Even after being threatened, Cremer planned on turning the site into "an informational website that basically lets people know what really happened." However, the site is now completely defunct.

L. Busacca/Getty Images

In 2002, a 13-year-old Taylor Swift sang "America the Beautiful" at the US Open. Her exceptional performance wowed many, including music manager Dan Dymtrow, who worked as a representative for Britney Spears at the time. Soon, Dymtrow started managing Swift, and their management contract lasted until July 2005. While the contract was active, Dymtrow launched Swift's career by helping her get in touch with various record labels, including Big Machine Records, which gave Swift a record deal after Dymtrow's contract had been dissolved.

That said, in 2007, Dymtrow filed a lawsuit worth millions of dollars against Swift and her parents. He claimed that he earned a total of $10,000 from the contract, despite being promised 5-10% of Swift's earnings from her work in the industry. Dymtrow also alleged that the Swifts and Big Machine CEO Scott Borchetta schemed to fire him so that Swift could sign the deal without paying him, even though the deal was essentially facilitated by Dymtrow. Out of Dymtrow's seven claims, six ended up being dismissed in 2008. Only one count of unjust enrichment against Swift and her parents was found to be valid. Firing Dymtrow without paying him the promised amount of money is definitely one of the many shady things Swift has done to get to the top.

Rick Diamond/acma2013

In April 2004, a 14-year-old Taylor Swift and her family moved from Wyomissing, Pennsylvania, to Hendersonville, Tennessee, as the budding singer had just signed a development deal with Sony Music's subdivision, RCA Nashville, the previous year, and traveling to Nashville had become a necessity. Thanks to Hendersonville being only 18 miles away from Nashville, the family's relocation helped make Swift's schedule a little less hectic, which, in turn, allowed her to focus on her singing and writing with more efficiency. That said, Swift terminated the development deal when she realized she was being kept from signing an actual RCA record deal for much longer than she had expected. Thankfully, Swift had already landed herself a songwriter's publishing contract with Sony/ATV Nashville when the development deal was dissolved, so moving to Hendersonville wasn't in vain at all.

Swift's parents played a big role in her becoming famous, and moving to Hendersonville was a huge sacrifice they made. Speaking of the relocation, the singer told CMT in 2008, "Living in Pennsylvania was great, and it was an incredible place to grow up, but I didn't have any friends, so I was like, 'Sure, let's move. I'll miss my friends even though I don't have any.' So that wasn't a big deal for me. But my dad had to transfer his work to Nashville. For a while, he was commuting back and forth and it was an incredible sacrifice for my parents to make and I've never forgotten it."