The Island Cup is always a day to circle on the calendar. But this year, it’s an event to circle with a bigger, bolder marker.

On Tuesday, the Martha’s Vineyard Regional High School football team will play against the Nantucket Whalers at Fenway Park, one of the biggest stages in the state. Kick off is at 5 p.m.

This is the first time the game will be played off-island, outside of Martha’s Vineyard or Nantucket.

Vineyard head coach Tony Mottola is looking forward to the experience.

Team goes over plays at practice this week. — Ray Ewing

“We’re excited to be a part of this rivalry with Nantucket, but then to actually play this game now in that type of an arena is just amazing,” Coach Mottola said. “It makes something that is already special a little bit more.”

The Island Cup has been officially played since 1978, though games between both teams have taken place since 1958. Vineyard athletic director Mark McCarthy said the history of the rivalry and its importance to both communities intrigued organizers at Fenway.

“When we had our first phone call with them, one of the comments they made was that they had never thought about what it’s like to play football on an Island,” Mr. McCarthy said.

The Vineyarders enter the game with a 6-4-1 record and are the Cape and Islands League champion. The Whalers are 3-8. But history is erased when the whistle blows on Tuesday and Island pride is on the line.

The energy has been palpable at practice, according to senior Guilherme Oliveira.

Head coach Tony Mottola. — Ray Ewing

“We’ve had this game in the back of our mind this whole season,” he said. “This week we’ve been going to practice, watching a lot of film, studying extra hard making sure we know what they are going to do, what they want to do and how they want to do it.”

The sentiment is the same on the sister island, said Nantucket football head coach Coreese Everett.

“The intensity in practices is different because of what the rivalry means and how badly each team wants to compete for the trophy,” Coach Everett said.

Football players are not the only ones enjoying the experience on the field at Fenway. MVRHS dance team sponsored by RISE will perform during the halftime show. 

“I’m just incredibly grateful that the dancers at RISE are getting to be a part of the Martha’s Vineyard High School fabric,” RISE director Jil Matrisciano said. “They’ve never really had that before. Now there’s this opportunity for them to represent their school and show their school spirit.”

Quarterback Guilherme Oliveira. — Ray Ewing

The Minnesingers will also be singing the national anthem with singers from Nantucket to kick off the momentous game. “I’m just really excited for the kids,” said director Abigail Chandler. “It’s a once in a lifetime opportunity.”

Leading up to the big day, the Martha’s Vineyard Touchdown Club will host a tailgate and car decorating party this Sunday at the regional high school. The party goes from 11 a.m. to 1 p.m. and will be followed by a parade through the down-Island towns led by police, fire and emergency responders.

On Tuesday, a fan bus heads to Boston, leaving at 2:05 p.m. from Woods Hole. There are still spots available. In Boston, a pre-game party will be held at Loretta’s Last Call outside Fenway.

“We hope the summer community comes and cheers along with us,” said football booster club member Elizabeth Barnes. “It’s a great bonding moment for everyone who loves the Vineyard.”

Although the Fenway experience is new for the Island Cup, high school football at Fenway has been a long-standing tradition. Brett Miller, director of business development at Fenway Park Events, said that of all the events and games hosted at the ballpark, these match-ups are some of the most special.

MVRHS dance team sponsored by RISE will perform during the halftime show.

“It provides this sort of once in a lifetime opportunity for hundreds of players and coaches and fans and communities, and that’s really what makes this all worth it,” Mr. Miller said.

For the seniors, thoughts of playing their last game as a Vineyarder weighs heavily.

“We’re in Boston at Fenway for my last game that I’ll ever be playing football against our rivals,” senior Calahan D’Arcy said. “The stakes couldn’t get any higher.”

Fellow senior Jordan Souza feels both excited and nervous to be playing on such a big stage.

“It’s very exciting,” he said. “I’m very anxious about it because I just want to show those thousands of people that I’m pretty good at this sport so I’m going to go out there and try my best.”

Minnesingers will perform at halftime. — Ray Ewing

For Mr. McCarthy, who played in the first official Island Cup back in 1978, he is looking forward to taking it all in from the sidelines.

“I’m just excited for the whole vibe of the day, what it’s going to be like to watch the kids come out of the Red Sox dugout,” he said. “Being in the Red Sox locker room and sharing that whole experience with them and seeing the memories that they are going to be forming around this game — it will be hard not to form a memory around this game.”

Those memories start on the practice field. On Tuesday, as the sun set on another practice and shouts of encouragement echoed in the air, senior Victor Desouza’s words stood out.

“We’re playing at Fenway,” Desouza said. “We need to win. There’s no other plan.”