The rivalry between Nantucket and Martha’s Vineyard has been a long-standing tradition, with the Island Cup being the showcase. Frank Schadt, documentary filmmaker and head of production at Nantucket Community Television, weaves that narrative into his documentary titled The Island Cup.

The film will be shown on NESN Monday evening at 6 p.m., and Tuesday at 3:30 p.m. The footage comes from the leadup to the 2018 and 2019 Island Cup games from both Island perspectives.

When Mr. Schadt moved to Nantucket, he was intrigued by the uniqueness of both Islands and how interwoven the Island Cup rivalry is in both communities.

“It sounded like a great tradition and very unique that the kids had to take ferries to their opponents and there’s an element of it being a sibling rivalry that attracted me,” he said.

Mr. Schadt said he began the project by filming Nantucket football practices, but quickly realized he needed more. He reached out to Vineyard athletic director Mark McCarthy and then traveled to Vineyard for the first time.

“I almost felt like a kid in the candy store and going from one side of the field to the other to film things,” he recalled.

He integrated himself into the team’s everyday activities on and off the field, including going to a linemen party with the Vineyard team.

“I was just shooting anything and everything and that’s how it proceeded until the Island Cup game,” he said. “I was about 10 years older than [the players] at the time. I didn’t feel like I was interfering with the vibe of the practices and the social gatherings when I would show up with a camera.”

“But I was always second guessing myself, thinking does my presence here affect all of this?” he added. “There was one time at Edgartown Pizza where one of the guys said that they don’t feel comfortable me filming [them] talking about classmates. So I stopped and told them when they’re ready to talk about the Cup again, I’ll come back.”

Mr. Schadt said he is proud of the holistic and intimate perspective his documentary gives of a deep-rooted rivalry outsiders may not fully understand.

“I feel like it was as close to an authentic portrayal of what it’s like to be a kid on the journey to this big game,” he said. “[This documentary] wouldn’t have been possible without the enthusiasm of the coaches, staff and students on both Islands.”

The Island Cup documentary streams on NESN on Monday, Nov. 25 at 6 p.m. and again on Tuesday, Nov. 26 at 3:30 p.m. This year’s Island Cup game begins at 5 p.m. at Fenway Park.