Saturday’s game for the Island Cup is one of the most-storied high school rivalries in the country, and the defining moment for a Vineyard culture that flourishes for three months every year.
But unlike the shedding trees or shrinking afternoons that mark the end of what is arguably one of the nicest times of year on the Island, football season goes out with a bang.
This year, the explosion takes place on Nantucket, as the 8-1 Vineyarders battle the 6-3 Whalers to keep possession of the Cup and represent the Mayflower League at the Super Bowl.
Cape Air is providing two additional inter-Island flights, and a special boat trip to Nantucket has been arranged to accommodate the droves of folks who are not only fans of the Vineyarders, but of the game itself.
High school students walking by the large trophy case in the lobby this week may have noticed a big hole where the cup has been sitting since last year. Earlier in the week, head football coach Donald Herman moved the cup into his office. It was a double-sided incentive tactic, he said, so the team could bring the cup to practice each afternoon and so everyone would see how empty the trophy case looks without its centerpiece.
But if walking every day by a trophy case sans Island Cup is not enough incentive, this year there’s much more on the line.
Two weeks ago, a loss to Blue Hills broke the Vineyarders’ 17-game winning streak and nearly dashed their hopes for playing in another Super Bowl. Because the team had represented its league last year at the game in Boston, another team with the same record as the purple would get to go this year. After Blue Hills defeated the Vineyard, it needed only to complete its year without losing to win a Super Bowl visit. “It’s out of our hands now,” was how Mr. Herman put it.
But last week, sitting in his office, Mr. Herman got a phone call. Thirty minutes later, he walked into the locker room where his players were preparing to go up against Weston and announced they were back in the race. Blue Hills had lost that afternoon to Bristol-Plymouth.
Now, one league game stands between the Vineyarders and the Super Bowl. If the Vineyarders lose Saturday, the season ends in Nantucket.
Currently with a 6-3 record, Nantucket is no longer a candidate for the Super Bowl, though it still can play the spoiler for the Vineyard. Win or lose, Saturday’s game for the Island Cup is Nantucket’s last as a team, its last chance for redemption after a lukewarm season, and its chance for revenge after a defeat that cost them the Cup last season.
The Whalers are also playing on their own soil this time, where the Vineyarders have not won since 1992. And for all of his championships, Mr. HermanÕs team has been less than successful against Nantucket, coming to Saturday’s game with a 5-7 record with him as coach.
The Nantucket team exhibits the hard style of play that overtook the Vineyarders in their loss to Blue Hills. The purple defense has been told to prepare for an early explosion of aggressiveness, while the offense needs to watch for frequent blitzing, a trademark tactic of the Nantucket defensive line.
But the Vineyarders are not without their ammunition. Nearly undefeated in the league they share with the Whalers, they face a team that has suffered two of its three season losses on the field where they play Saturday.
The Vineyarders may be away from home, but the army of fans taking boats and express flights to Nantucket will do much to balance the crowd.
“It almost feels like a home game,” Mr. Herman said. “It’s a great situation.”
And though this year’s squad is physically smaller than the one that took the Island Cup home with them last year, it is also faster, and has proven its ability with an outstanding season on what was originally planned to be a rebuilding year.
Senior co-captain Jeff Lynch, who had the best game of his football career against Nantucket last season, will help lead the quick and compact offensive line.
Leading the defensive squad will be James Hagerty, backed by a power trio of sophomores including the young but rock-steady Ted Desrosier.
Ryan Smith and co-captain Geoff Phillips will lead the special teams, who have been a cornerstone to this season’s impressive record, picking up where a sometimes thinly spread offensive line left off.
The forecast for flurries also looks to be on the side of the Vineyarders, who won a state championship the last time they played in the snow. The weather also looks unfavorably on Nantucket’s all-star running back Alex Richardson, who brings to the field a quick run-and-gun style of play difficult in sloppy conditions. 
“He’s fast and needs to plant and cut,” Mr. Herman said, explaining how soggy turf might handicap Nantucket. “If it’s wet, he can’t do that.”
Weather, fans and histories aside, pressure is also a major element both teams must face. With the Super Bowl at stake along with the Island Cup, along with all the banners, press attention and boatloads of fans, more pressure is added to the backs of the Vineyarders - pressure, Mr. Herman says, that will dictate if his team wins or loses.
“That’s going to be the bottom line, is how do we respond to this environment and pressure on Saturday.
“I tell them, play every play in this game like it’s your last one, because you never know what play during the course of the game is going to determine the outcome,” he said. “You don’t want to leave that field with any regrets.”
The varsity kickoff is at one o’clock Saturday afternoon on the Nantucket field.