On a cool, sunny afternoon outside of the Westport Country Playhouse, families gathered listening to holiday music, tossing bean bags into a hole, making clay snowmen and drinking hot chocolate.
The Westport Country Playhouse hosted a Winter Fun Fest on Dec. 4, organized and run by the Playhouse Youth Council, to raise money for Homes with Hope and attract a younger audience to the theater.
“The Youth Council of the Westport Country Playhouse has organized a Winter Fest, trying to attract really young kids,” Cessa Lewis, member of the Council, said. “We’ve got different winter activities—a story reading, hot chocolate, fun games and snacks—to bring the community together.”
Westporters and people from neighboring towns attended. Greenwich parent Adam Potter came with his two 8-year-old daughters.
“[We came] because we often come to see a lot of the kids’ shows here,” Potter said. “This is a nice place, and it’s fun for them to get out and do things like this.”
During the event, there was a food drive for Homes with Hope. Any guest who donated was entered into a raffle for a pair of tickets to a show in the Playhouse’s 2022 season.
“Homes with Hope is a homeless shelter, so they provide support and shelter for people who are homeless in Fairfield county, or specifically Westport, especially during the holiday season,” Kate Davitt ’22, another member of the Youth Council, said.

Long Lots student Alice Forde showed her passion for the event and for the cause behind it, speaking about the significance of raising money for homeless people, not only in the holiday season, but all year round.
“We should build a shelter for the people who don’t have money in the winter,” Forde said. “And we should, in the summer, […] have food drives, toy drive drives, blanket drives in different schools to give to people who need [it most].”
From 12 p.m. to 1 p.m., the Staples Orphenians and Chamber Orchestra performed holiday carols on the terrace of the Playhouse.
“Playing at the event was a great community building experience for an awesome cause,” cellist Rebecca Schussheim ’23 said. “I loved that I was able to help support Homes with Hope and all that they do while also having a great time performing and listening to holiday tunes from our combined Chamber and Orphenians.”
Overall, it was a successful event that brought the community together.
“My favorite thing,” Riverside School students Wallace and Peggy Potter both said, “was spending time with my friends and sister.”