"They called like a million numbers before they got to me," Weston said of the raffle. "When they called my number, I was like 'Oh my God, it's unbelievable!'"
She will likely have no shortage of offers to attend the game with her.
"Hey, do you need a date?" a man wearing a vintage Ted Williams No. 9 Red Sox jersey asked Weston as she left Fenway through Gate D onto Yawkey Way.
"No way," said Weston, a stay at home mom and one of the few at Fenway who didn't have to play hooky to be at the rally. "I'm taking my daughter."
Weston's daughter, Ashley Whorf, will celebrate her 16th birthday Thursday.
"This is her sweet 16 present," said Weston. "I can't hide nothing from my daughter. I'm too ecstatic to."
The day started with Charles Steinberg, the Red Sox's executive vice president of public affairs, welcoming the crowd from a temporary stage -- constructed after Sunday's 10-1 playoff-clinching win over the Yankees -- in front of the Red Sox first-base dugout. Steinberg explained the 86 years between Red Sox World Series championships had added significance to Red Sox fans because it was also the birthday recently celebrated by Sox legend Johnny Pesky, who joined Steinberg on stage.
With the grounds crew tending the Fenway infield behind him, and helicopters hovering above, Pesky fielded questions from the crowd, including his thoughts on who should be the American League MVP.
"David Ortiz has to be MVP," Pesky answered, much to the delight of the crowd.
Ortiz, along with manager Terry Francona, pitcher Matt Clement, first baseman Kevin Millar, general manager Theo Epstein, and NESN broadcaster Don Orsillo, appeared live from Chicago on the jumbo video board in center field.
Peggy Anne Canty, 72, of Dorchester, sat in Section 16, wearing a Red Sox hat with her friends Patricia Slavin, 63, a season-ticket holder from Newton, and Kathleen O'Brien, of Mission Hill, who gave her age only as "old as my tongue and older than my teeth."
"I just think it's a wonderful opportunity for people who cannot dream of having tickets to the game to be part of the celebration and the playoffs," said Canty, whose favorite player is Jason Varitek.
Each of the eight teams in the playoffs will host a rally before the postseason begins.
"It was a great idea from [Major League Baseball] that the teams around the country that have qualified for the postseason [have a rally]," said Red Sox president/CEO Larry Lucchino. "There's a special effort to fire up the fans. Here in Boston, we don't really have to worry too much about firing up our fans, they are the real deal.
"These are some of the truest of true believers to come out at noon on a Monday to participate in the pep rally, and we're lucky to have these kinds of dedicated fans."
Ashley Prien, 17, and Star Alston, 16, both of Lowell, each sported a blue 'B' on their faces after visiting the face-painting booth on the main concourse. The girls had skipped school to attend the rally.
"I heard about [the rally] on the news, and I was like, 'I love the Red Sox, so I have to go,'" Prien said. "I go to UMass Lowell. I only have two [classes] today, so that isn't too bad. I couldn't make it to any Red Sox games this year [because they were] too expensive, so this was a good thing to go to."
Anika Larsen, 31, a Cambridge native who has worked in New York for 10 years, traveled from her Brooklyn home to attend the rally with her mother, Pam Larsen, and brother, Peik Larsen.
"It's a hard place to be a Red Sox fan. But I got this just to make things clear," said Anika Larsen as she showed off a new T-shirt that read "Red Sox Girl. Enough Said."
"I can't wait to wear it in New York."
Cliff Ducheine brought his two young sons, Lee, 3, and Raw, 2, for their first trip to Fenway Park.
"I brought the kids to see some history," said the 30-year-old Ducheine, who lives in Boston. "It could be a once-in-a-lifetime opportunity with my sons."
"He's going to be a future Red Sox base stealer," Ducheine said of Lee, who had suddenly bolted.
Asked if he was playing hooky for the day, Ducheine replied: "Well, yeah, but shhhh. Don't tell my boss."
His friend, Ja King, 35, of Boston, who had caught Lee before the youngster could get too far, was one of the few not skipping work or school.
"No," he said. "I got off work at 8:30 this morning and came here."
Roland Leger may have traveled the farthest to attend the rally. The Cambridge native now lives in San Luis Obispo, Calif. He was in town over the weekend in the hopes of attending the Red Sox-Yankees games. He managed to get a ticket for Sunday, but watched the first two games of the series from a sports bar.
"When I heard about this, I had to call in sick," said Leger, who works for the state of California, delaying his return flight until Monday evening. "I never call in sick, but you have to do what you have to do.
"This is cool. To be able to have this for the fans is very important. It's a nice thing, nice for people to come out and support the team. It's a great ballpark, a lot of history, a lot of tears, a lot of fun. I'm honored to be part of this."
The first ALDS game at Fenway Park is Friday at 4 p.m. ET. If you're at the game, stop by Box 111 and wish Ashley Whorf a happy 16th birthday.