On November 26, the Nantucket Whalers varsity football team will not be playing their Thanksgiving week Island Cup game on Nantucket or Martha’s Vineyard, but at Fenway Park. When head coach Coreese Everett and his players first learned the news in August, it sparked an excitement that has driven the team to improve day after day.

“My first reaction, of course, I was very, very excited,” Everett said. “You know, things like this don’t always come to programs that easy. This is a once-in-a-lifetime opportunity. I am excited because this is an opportunity that the kids get to experience and hold and cherish for a lifetime.”

While Fenway today is synonymous with Red Sox baseball, the ballpark has hosted its fair share of football games over the past 100 years, including a 1927 game between the New York Giants and a South Boston-based football team called Pere Marquette (the Giants won that game 33-7). Fenway first hosted high school football just months after it opened in 1912, in a rivalry game between Boston Latin and Boston English. Two days later, Everett High School took on Oak Park, Illinois, in the 1912 high school football national championship game (Oak Park won 32-12).

The ballpark became a popular venue for high school and college football games throughout the 1920s, ’30sand ’40s, as the Red Sox entered what would become an 86-year championship-free rut. The Boston College Eagles and Boston University Terriers called the park home in the ’30s and ’40s. In 1940, a game between Boston College and Georgetown was lauded by late Boston Globe columnist Grantland Rice as “probably the greatest football game ever played by colleges or by pros.” And one Boston University game in 1949 was announced by legendary Los Angeles Dodgers announcer Vin Scully. Fenway was even home to five professional football teams through the 1960s, including the Boston Shamrocks and the Boston Braves, who later changed their name to the Redskins and moved to Washington, D.C.—the team renamed themselves again as the Commanders in 2022.

The last scheduled college game of the 20th century at Fenway was set for November 1963 between rivals Boston College and Boston University, but it was scrapped at the last minute following the assassination of President John F. Kennedy. It marked the beginning of the end for Fenway football. After the Boston Patriots left Fenway for Foxborough—via Alumni Stadium and Harvard Stadium—in the late 1960s, the park entered a 47-year period without any football, a stretch that was finally broken in 2015 when Boston College took on powerhouse Notre Dame, a game the Eagles lost 19-16. Fenway has since hosted high school football games every year since 2021. Nantucket’s game is one of just four high school games being played there this year.

“This is a pretty unique opportunity for these kids,” Nantucket Public Schools Athletic Director Travis Lombardi said. “Obviously, it’s for the kids but [for]our town and our community as well. I know there are a lot of other rivalries that applied for this, but for us to be selected is a huge honor for both us and the Vineyard. We’re really looking forward to it, and it’s definitely going to be a little bit different. The atmosphere is not going to be as intimate, I get that. But just the whole experience and the environment and the atmosphere is going to be something that these kids in this community are going to remember for a very long time.”

Assistant head coach Mark Willett, who has been on the Whalers’ coaching staff for over a decade, said the team has taken a week-by-week approach all season, but the Island Cup looming at the end of their schedule has kept them focused.

“I think the Island Cup is always like a carrot at the end of the stick because it’s always towards the end of the season,” Willett said. “Now it’s even bigger and it’s a great showcase. I mean, one of the best rivalries in New England high school football, right? Playing everybody’s favorite sport in everybody’s favorite park. I think they’re working hard for it. I think some, especially the upperclassmen, the ones that lost the cup, they know. They know what it’s about. They’ve seen the cup not come home with them on the boat, and they’ve seen the cup leave this island. They know and they’re working for it.”

The last time the Whalers won the Island Cup was on October 31, 2021. After a somewhat slow start, they won comfortably 27-7 on Nantucket that day. But since that game, the Vineyarders have rattled off wins in two consecutive Island Cups—beating Nantucket 14-13 in 2022 on the Vineyard and 24-21 in 2023 on Nantucket. The Whalers failed to qualify for the playoffs in either of those seasons and went a combined 4-15in 18 games. But the Whalers are starting anew era under Everett and realize a victory in Boston would send a message to the Cape and Islands—and Martha’s Vineyard, in particular—that Whalers football is on its way back to being a winning program.

“When I first heard about the game being at Fenway Park, I was really shocked and surprised because I didn’t know that was an option, but the opportunity just to play at Fenway Park with a lot of the state’s biggest rivals is really cool and a once-in-a-lifetime opportunity that I’m excited for,” said Owen Sullivan, the Whalers’ senior running back, linebacker and captain. “I think the game being a few weeks after our regular season ends is a good thing because it encourages us to get better through the end of the season, and it really allows us to get prepared for that game as we all really want to get the cup back.”