NANTUCKET SOUND — One of the best Thanksgiving football rivalries in Massachusetts is not played on Thanksgiving. If it were, no one would be home in time for dinner.
Nantucket vs. Martha’s Vineyard has everything that makes high school football great: heated competition, thrilling finishes, generations of stories, myths, and legends. Massachusetts has shades of that everywhere. But this is the most unusual rivalry we have to offer.
Where else do the participants see little of life on the mainland, spend hours on boats traveling to away games, and convoy with hundreds of fans who are all but guaranteed to stay for all four quarters? What other victorious team returns to a celebratory blaring of fire-truck horns and police sirens?
This year, a twist: This quirky contest is coming to the mainland.
The 44th edition of the Island Cup — and 75th meeting in the schools’ history — will be played at Fenway Park on Tuesday.
Two islands with a combined year-round population that would just about fill the ballpark, and nine state titles between the schools. If only it were a decider for a Super Bowl berth.
It’s the first time both teams — not just one — will ferry to the game.
’No, my parents work for the rich’
The Island Cup has never been a showcase for future stars. The schools have a combined enrollment of less than 1,200, and college recruiters like to hit more than one school in a day. Nor is it a reinforcement of anyone’s reputation as an affluent enclave.
“The islands might be playgrounds for the rich, but the people who live here aren’t,” Vineyard athletic director Mark McCarthy said. “Our kids will go places and people will say, ‘Oh, you must be rich.’ No, my parents work for the rich.”
Well-off people — some famous, some not — spend their idle weeks on these shores. Once the weather cools and the ferry service slows, the islands grow dark and quiet. Year-rounders hunker down. The football turns nasty.
Bragging rights mean everything. Still.
There has been enough drama in games between these islands located 7 miles (Martha’s Vineyard) and 30 miles (Nantucket) off the coast of Cape Cod that author Buzz Bissinger, a former Nantucket summer resident, considered writing about Vito Capizzo before setting “Friday Night Lights” in West Texas.
“It’s the one everyone goes to,” said Wall Street Journal columnist Jason Gay, a Belmont native who started his career at the Vineyard Gazette. “You can have a terrible year but knock out your Island Cup opponent, and it makes your season.”
The teams first played each other in 1953, seven years before Martha’s Vineyard Regional High — a combination of high schools in Edgartown, Tisbury, and Oak Bluffs — was founded. McCarthy’s father, Dan, found early success as coach, shutting out Nantucket five times in eight games from 1962-65.
Capizzo changed that. A walk-on under Bear Bryant at Alabama, he arrived in 1964 and turned Nantucket into a football power in his 45 years coaching the Whalers. Capizzo, who retired in 2009 and died in 2018, was a Sicilian immigrant who grew up in Natick and found his way to Nantucket after initially believing he was answering a job call in Nantasket. His name is on the football stadium, which to this day remains little more than sandy grass surrounded by saltbox outbuildings.
By the mid-1970s, the Vineyard was up, and the sides decided they needed a prize. That summer, Vineyard coach John Bacheller crossed Nantucket Sound on a 16-foot skiff and returned with a $127 piece from Falmouth Trophy Store.
“The nicest one they had,” he told the Vineyard Gazette in 2003.
Capizzo was supposed to pay for half of it, the story went, but the check was lost.
After the top-heavy original broke in half several years ago, then-Nantucket AD Chris Maury bought a redesigned, solidified replacement for about $400. Maury paid in full, McCarthy said, “because I don’t want to hear any crying from you guys.”
At stake: A trophy and so much more
Hours before a Nov. 8 game against Falmouth, Nantucket athletic director Travis Lombardi walked down a hallway underneath a ceiling-mounted 47-foot skeleton of a Finback whale, and opened the doors.
The wind whipped across his face and over the football field, sending the nearby windmill into a frenzy. He checked his watch again.
It was 3:05 p.m., and no text came from Falmouth’s AD. The visitors were leaving the dock. Game on.
“We’re always looking at the weather,” Lombardi said. “Our kids and our coaches are used to it. If the boat doesn’t run, they get it.”
For the Fenway game, Hy-Line added an extra return ferry at 9:45 p.m. It sold out quickly. Some families will have to stay overnight on the mainland.
The Cup is at stake. Of course it’s worth it.
From ‘78 onward, Nantucket won 10 of the first 11 Island Cups, beating the Vineyard by a combined 259-62 with six shutouts. The outlier was 1985, when Vineyard defensive tackle Erik Blake blocked a punt and returned it for the go-ahead score in a 12-2 win.
That one might have been on the coach. Capizzo, awash in hubris, forgot to bring the trophy to the game. His teams had that kind of swagger and shtick.
“We were just rocking teams,’” said Joe Perry (Nantucket ‘82), who later coached the Whalers. “We walked in saying, ‘We own this place.’ ”
Not in ‘85. After the Cup stunt, those players were even more fired up when they saw Nantucket’s pregame parade.
“They had our quarterback as a mannequin, with his jersey on, with a harpoon stuck in the back,” recalled Mike Joyce, a senior on the ‘85 team. “They put it in a truck and backed it right up to the field.”
Communities unlike any other
Like many Vineyarders, junior middle linebacker Syius Rivera doesn’t know many Nantucketers. Most of his teammates have been there only for games. But he believes there is a common understanding between the two.
“We go to play other teams and they just think we’re rich, entitled white kids,” Rivera said. “That’s not who we are. I think they understand that. We’re these little islands trying to prove to the rest of Mass. and the Cape that we’re something.”
Standing next to him outside Vineyard’s locker room hours before a Nov. 15 game against Nauset, junior running back Guilherme Oliveira described island life as pleasant, if isolating.
“On the outside, people think it’s weird that we live here year-round,” said Oliveira. “You have limited access to things.”
The Vineyard, like Nantucket, still plays on natural grass. The Vineyard has one more stoplight than Nantucket (none). Neither has chain retailers or restaurants other than Stop & Shop and Cumberland Farms. The time commitment to leave the island — especially in the offseason, when ferry service is light — means many rarely do.
Between trips to the orthodontist, buying soccer cleats, enjoying some Dunkin’ Donuts … the off-island to-do list can get long.
Michelle Keeler, a post-college washashore (as islanders call them), thought she would stay one summer. A generation later, she still goes to games even though her son, Evan, headed off-island for culinary school two years ago.
“If the weather’s bad, they’ll run out of bread in the grocery store, and you have to adapt,” said Keeler, as she watched Nantucket play Falmouth, the wind settling into a peaceful twilight.
She hopes Evan will return as a fully trained chef, open a restaurant, and make his way on the island. She isn’t confident that the exorbitant real estate prices will allow it.
“Your kids will realize one day how special this place is,” she mused.
Some already do.
“It’s easy to build a community,” Oliveira said. “Everyone knows each other. We have no choice. We all live next to each other. We all have respect for one another.”
Cue the fire trucks
After teaching his fitness classes at the YMCA across the street from Vineyard’s football field, Donald Herman arrived for a 6 p.m. kickoff against Nauset and stood at the northeast corner of the end zone, near a light pole where an adult male osprey — fierce, territorial, loyal, a hunter of fish, something of an unofficial mascot for the Vineyarders — had built a nest.
Retired but still riding the wave of every play (“Aw come on, tackle him!”), the sharp-eyed Herman looked and sounded like the coach who evened the score.
Herman grew up in Savannah, Ga., married an island girl, and took a one-year position as a gym teacher/football coach in 1988. Herman, who retired in 2016 (and again in 2021), is a major reason the Vineyard holds a 22-21 lead in games since 1978. The Vineyard has lost five times since 1999.
He and Capizzo “hit it off immediately,” Herman said, and were lifelong friends. But Herman quickly saw Capizzo’s Auerbachian side. He noticed Nantucket’s visiting sideline was a lot sloppier and muddier than the home sideline.
“He must have thought I was stupid,” Herman said. “My first year, he’d call me during the season: ‘Hey, we’re playing so-and-so, they run the three-fifty — what would you do against that?’ C’mon, now.”
The Vineyard lost Herman’s debut, 14-0, in 1988. But Herman — whom Capizzo playfully nicknamed “The Snake” — earned revenge in 1989, and handed Capizzo some of his most painful losses. Like in 1992, which may have been the best Island Cup. Both teams were 8-1, a Super Bowl berth was on the line. The Vineyard hadn’t won on Nantucket since 1972.
The visitors trailed, 12-0, with 4:41 left when receiver Albie Robinson laid out and made a foot-dragging fingertip catch in the back of the end zone. They forced a punt and scored again. Some 1,000 people partied on the ferry back home.
“We pulled into Vineyard Haven, and every ambulance, police and fire truck is there, going off,” Herman said. “It still gives me goose bumps.”
Then there was the Waterboy Game in 2004.
After Vineyard blocked a punt in the final minutes, kicker E.J. Sylvia made a 29-yard field goal with two seconds on the clock for a 21-20 lead. He kicked off, and after a lateral, Nantucket’s Adam Goodwin fumbled as he was hit.
Martha’s Vineyard, believing Goodwin was down and the game was over, poured onto the field. Nantucket’s Brennan Dooley — who had run back the game’s opening kick for an 89-yard touchdown — picked up the ball and ran. He raced up the sideline, dodging players and fans, and was finally brought down.
Lending a hand was Brenden Maseda, the Vineyard’s 10-year-old waterboy, who accidentally ran in front of Dooley.
“They were saying, ‘Aw, we should have gotten another play, there were too many people on the field,’ ” Herman said. “You’re right, but … the referees didn’t even hesitate. They took off. They ran.”
Both Nantucket and Martha’s Vineyard will leave the Port of Fenway with enough fish tales to fill an offseason.
Two ships will depart late Tuesday: one from Woods Hole, the other from Hyannis. One sullen and sore, one toasting to a trophy under sky and sea united in dark, until they reach the party at the dock.
Matt Porter can be reached at matthew.porter@globe.com. Follow him on BlueSky at mattyports.bsky.social.