PHOENIX – Baseball is a kids’ game, and Williamsport, Pa., is where kids first realize their big league aspirations.
The Cubs are returning to the kids’ baseball capital on Aug. 19, 2027, as they’ll face the Blue Jays in the 2027 Little League Classic in Williamsport. It will mark the second time in franchise history that the Cubbies will participate in the preeminent cross-section of the game’s future and its present.
The contest will mark the 10th iteration of what is now one of Major League Baseball’s jeweled events on the regular-season calendar. To boot, the contest will take place on a Thursday for the first time, allowing the game to serve as the headliner of ESPN’s all-day coverage highlighting baseball in its various stages.
There are 10 players who previously played in the Little League World Series and have gone on to appear in a big league game during 2026, including Cubs outfielder Michael Conforto.
Conforto has arguably the most well-rounded perspective of the entire event, as the veteran outfielder played in the 2004 LLWS for Redmond North from Washington state and in the 2018 Little League Classic while with the Mets. New York topped the Phillies 8-2 in that game, and Conforto’s full-circle moment was complete.
Many MLB players channeled their inner child during the 2018 visit, including Conforto.
“The memories came rushing back,” the 33-year-old Conforto said. “We met the kids, I saw them trading pins and some of the guys went to slide down the hill.”
Back in 2019, the Cubs – donning unique gray threads that featured “Cubbies” across the chest and players’ nicknames on the back – topped the Pirates, 7-1 in the Classic. But beyond the game, manager Joe Maddon threw out a first pitch before Little League action and Anthony Rizzo slid down a berm on a cardboard box.
Ian Happ is the lone member of the club’s current roster to have participated in the 2019 iteration, having entered as a defensive replacement. But even as a then-25-year-old, he got to take in the splendor of the event:
“It was really special to do that,” Happ said. “It’s a cool event. Just to be around the kids and see the energy. It’s such an amazing facility, just how big it is and how much is going on. It was really special having [Yu] Darvish on that team and his connection with Team Japan, getting to hang out with the kids before and play ping pong, all that stuff.”
Ping pong is a staple of the event, as Brewers ace Jacob Misorowski found out the hard way on Sunday. Overall, the various activities give kids an opportunity to interact with some of their favorite big leaguers while enjoying downtime during their World Series run.
“Whenever you see people on TV from those games, they look like they’re having fun,” manager Craig Counsell said. “I’m looking forward to it.”
Conforto echoed that sentiment, and praised the way Major League Baseball officials have organized the event.
“I think it's one of the cooler things that MLB's done,” Conforto said. “The dream of actually playing baseball professionally started there. I went out there, I played well, and that’s when I knew if I kept working as hard as I could, maybe I could do this for a living.
“Letting kids meet and talk with Major League players will inspire them even more. It would have for me.”