Cubs Return to Williamsport for 2027 Little League Classic
The Chicago Cubs are heading back to Williamsport, Pa., for the 2027 Little League Classic, where they will face the Toronto Blue Jays. MLB Commissioner Rob Manfred made the announcement Sunday night, confirming that the game is scheduled for Thursday, Aug. 19, 2027, and will air on ESPN.
The Cubs, who will be the road team, will have the following day off before playing two more games against the Blue Jays in Toronto over the weekend. This will be the 10th edition of the Little League Classic, an event that began in 2017 and was skipped in 2020 due to the pandemic.
A Storied History
The Cubs have a history with the event, having participated in 2019 when they beat the Pittsburgh Pirates 7-1. Ian Happ, the team's left fielder, was part of that squad and recalled the day fondly.
"It was a really cool day," Happ told the Chicago Tribune. "Of all the events we've played in over the years, it was probably the busiest. ... The most memorable part of the day was just being out there with the kids and touring everything. But it was really cool to be a part of."
Happ, a Pittsburgh native, never played in Williamsport as a Little Leaguer, but he remembers driving through the town on the way to another tournament, making a pit stop to see how packed Bowman Field was for the Little League World Series.
Michael Conforto, who now plays for the Cubs, brings a unique perspective. He was part of the 2018 Little League Classic with the New York Mets and, as a kid, played in the 2004 Little League World Series for Redmond North from Washington state.
"It was the ultimate baseball experience for me up to that point," Conforto told the Tribune. "And then I rode that through the rest of my youth sports playing time."
His memories of that time are vivid: the pool, pin trading, the barracks, and the arcade, which he described as his version of Disneyland. He recalled being amazed that ESPN cared enough to broadcast the Little League World Series, with Harold Reynolds calling the games.
"It was the ultimate baseball experience for me up to that point," Conforto said, reflecting on the sense of accomplishment the tournament gave him. "It gives kids a great sense of accomplishment and a reward for all the hard work they've done."
Conforto is one of only three players to have appeared in the Little League World Series, the College World Series, and the MLB World Series, a testament to the lasting impact of his youth baseball journey.
A Marquee Event for the Cubs
The Cubs have become frequent participants in MLB's special events. Since their 2019 appearance in the Little League Classic, they have played in the Field of Dreams game in 2022, the London Series in 2023, and the Tokyo Series in 2025. Happ acknowledged that being a Cub often means being invited to marquee events, and he hopes to continue being part of them.
The Evolution of the Little League Classic
According to Newsweek, the inaugural Little League Classic took place in August 2017 between the Pittsburgh Pirates and the St. Louis Cardinals. Since then, the event has featured matchups like the Mets vs. Phillies in 2018, the Pirates vs. Cubs in 2019, the Guardians vs. Angels in 2021, the Orioles vs. Red Sox in 2022, the Nationals vs. Phillies in 2023, the Yankees vs. Tigers in 2024, and the Mets vs. Mariners in 2025. This year's edition saw the Atlanta Braves defeat the Milwaukee Brewers 4-2, with players from both teams interacting with Little League World Series participants throughout the weekend.
According to MLB, more than 70 former Little League World Series players have gone on to play in the majors, including 10 who appeared in regular-season games in 2026, such as Cody Bellinger, Michael Conforto, and Ceddanne Rafaela.