On a rainy Friday night in March, seconds after Ry McDonald introduced his band to columns of seated tables at The City Winery in Boston, the tinny, incredulous voice of a seven-year-old cried out, “Are you guys actually copilots?” 

McDonald just grinned and declared, “I love this. The whole performance will just be a Q&A,” later riffing, “similar to Microsoft’s AI, we’ll answer all your questions,” earning a loud chuckle from the charmed audience. 

The pop-rock band Copilot exuded the easygoing energy of a group that’s been playing together for ages. And at its helm are two alums from King Philip Regional High School: Ry McDonald and Maggie Hall. Their set opened with McDonald casually noodling the guitar before Hall’s steady, powerhouse voice snapped the room to attention. Throughout eight songs, three singers traded lead, effectively ramping the energy for upbeat shouts and mellowing down for soulful ballads. 

The Boston-based band kept busy in 2025: they released the EP titled “Vroom Vroom, Etc.,” performed at popular music festival Boston Calling, and launched a GoFundMe campaign to support their forthcoming album, raising over $30,000 with the help of an angel investor. 

McDonald and Hall both graduated from KP in 2010. While acquainted, they were not close friends. In fact, they probably would’ve made an unlikely duo back then, like in a teen movie where the confident kid in a rock band persuades the sweet, shy jock to sing with him.  

“I remember Ry was the guy who came out with his guitar and sang in front of the class,” Hall said. “I [thought he was] the most talented kid in our grade…but I was a closet singer at that point.”

“I wasn’t the best student,” McDonald explained. “But I found out very early on that if I ever brought my guitar in for a class project, the teacher would just give me an A.” 

McDonald was raised in Norfolk and inherited his knack for guitar from his musical parents who sang in a cover band, rehearsing on Thursday nights, and playing gigs some weekends in local spots around Wrentham. McDonald would accompany them to shows and, by age 12, started performing a couple of songs between their sets. 

“They always had the equipment around,” McDonald said. “So, when I was in high school, I knew I could borrow the PA [speaker] my parents had and bring it to a party and play music.” 

The name “Copilot” alludes to a McDonald family memory. Before semi-annual road trips down to Florida, his uncle would make 250-song cassette mixes that served as the car’s only soundtrack. “It was my first time hearing a lot of the music that made me want to be a musician,” McDonald said. “And the only time my dad would let me stay up late... He’d say, ‘you can come be my copilot while we drive.’”

Meanwhile, softball defined much of Hall’s identity growing up. Hall, née Quealy, originally from Plainville, was an all-star pitcher who helped her team clinch the Hockomock league title all four years, earned a full-ride sports scholarship to UMass Amherst, and was inducted into KP’s Athletic Hall of Fame in 2023. Her 15-minute walk home from school became her daily singing time, and she even declined offers for rides so she could have the time for herself.

“Though my neighbors later told me, ‘We could always hear you,’ and I was horrified,” Hall shared with a laugh. “Me practicing The Star-Spangled Banner by myself.”  

“There were little traces of Maggie’s singing power but they were hidden,” McDonald added. 

Though Hall kept her passion and talent for singing largely private, Peter Tileston saw it. The longtime King Philip choral director led the school’s music program for more than 27 years before retiring in 2010. Hall participated in choir throughout high school and worked with Tileston individually in preparation for districts auditions. 

“Right from the beginning, Maggie displayed a talent with her voice and her ear,” Tileston said. “She always sang right in the center of the pitch and…[was] a leader for the rest of the kids because she followed my directions and she changed them and got better.” 

Despite their shared musical interest, the future bandmates did not connect until 2016 when McDonald saw a video Hall had posted on Facebook of herself singing and, impressed, reached out to her. 

“I would text her pretty much every day and [ask], ‘Do you want to come hang out and we’ll sing?’” McDonald said. “Then we just started doing that all the time.” And almost a decade later, they have not stopped. 

Their first show was at The Gavel in Wrentham center and, while singing in public was natural for seasoned McDonald, Hall recalled feeling “terrified.” She’d joined an acapella group her junior year of college, but harmonizing with one other person on stage was a new experience. 

“I was so nervous,” Hall said. “But I remember the thrill I would get afterwards.” 

Soon, the duo was performing in restaurants and bars across New England and New York. They eventually recruited bassist Austin Beveridge and drummer Dylan Allwine, both of whom McDonald had met while studying Music Business at Northern Vermont University (then named Lyndon State College) and in 2017 recorded their first album in an Airbnb. By 2018, they’d added vocalist Jake Machell and lead guitarist Jack Snow—and thus, the crew was complete. 

When it came to composing original lyrics, McDonald already had a host of songs from previous projects but knew Hall’s emotive voice called for new material, encouraging her to write from a “real place” and as much as she could.  

“I came in with just a true blank slate,” Hall said. “I’ve learned so much from Ry about songwriting and saying something that people have said in so many songs but [thinking about] how do you make it unique to you or how do you sing it differently. And I think Ry always challenged that part of myself in particular which is really cool.” 

“I think with most creative acts where people are doing things for the first time, you just kind of guide and encourage and show a little belief and you get there,” McDonald said, and that philosophy clearly shines in Copilot’s collaborative, no-secrets approach to songwriting where everyone contributes lyrics. Bassist Austin Beveridge, for example, wrote “Bang Bang Boogie,” on the latest EP. Working with Sam Kisserer, the producer behind Lake Street Dives’ Bad Self Portraits, marking a turning point: the band’s first time recording with someone who wasn’t a friend or classmate.

Keeping a band together is notoriously difficult, especially a six-piece for eight years, but Copilot has maintained the same core members since assembling. McDonald said the trickiest hurdle is often scheduling around other jobs, partners, families, and homes scattered across Massachusetts.

“Every time I’m on stage, I call the boys my ‘merry men,’” Hall said. “I don’t think I was prepared for the family I would gain.”

Copilot is currently working on their third album. “We’ve approached the writing process differently,” McDonald said. “We love playing live, we thrive in a live space, we built the band in order to be a really strong live band…this go-around we’re recording with a click track but keeping things as live as possible…trying to mess with it on the go so we can transfer our live show onto a record.” 

Until then, you can catch Copilot at their concerts across the Eastern seaboard: https://www.copilotband.com/shows.