By Julie O’Brien Deasy
On a beautiful spring evening approximately 450 New Canaan residents gathered at the Roger Sherman Inn to celebrate and take photos ahead of Junior Prom with the Class of 2027. This longstanding tradition had been absent in recent years, and judging by the enthusiastic turnout from students and families alike, its return was warmly welcomed by the community.
NCHS parent Jayne Benton, owner of Elm Street Events, partnered with the Roger Sherman Inn to host this year’s junior pre-prom gathering on April 17. With support from New Canaan High School and the NCHS PFA in promoting the event, the evening was a tremendous success.
“The first goal was to bring back this fantastic post prom event, and have a place for all the students and parents to gather. I love all the New Canaan traditions, and this is such a fun one,” observed Benton, a long time New Canaan resident. “We also wanted to reintroduce the Roger Sherman Inn to the town, so people could get to know the new owners and see how they are updating the property.”
Parents and students mingled for a few hours on the front lawn, taking pictures and catching up with friends. Before heading off to prom, the evening concluded with the famous “rainbow” picture of all the girls lined up according to dress color.
Students appreciated the chance to see all their classmates together as a class. “Pre-prom was great because I could see all my friends in one place and catch up before Prom,” said Junior Henry Reagan.
Roger Sherman Inn provided complimentary passed hors d’ouerves and soft drinks, and had live music, fire pits, and a photographer present to capture the event. Parents in attendance appreciated the event as much as the students.
“Junior Prom was amazing. It was so nice to see so many kids and parents we hadn’t seen in ages. We ended up staying for dinner with some friends at the Roger Sherman after the kids left. It was great – highly recommend the seafood risotto. We are so glad they brought back this tradition,” noted Sarah Hering, parent of a current Junior.
Brianna and Uanderson Benedetti purchased the Roger Sherman last year and were excited to help bring back this community tradition. “My family loves this community, and we think this property deserves a special place in it,” Benedetti said. He wants “the property to be a gathering spot for everyone in New Canaan.”
The Roger Sherman will be opening its doors again on May 15 to celebrate Senior Prom. Families are welcome to arrive starting at 5:00 PM, with the full class photo at 5:45 PM. This free event is open to all seniors and their families.


