By Aya Goldwasser, Backpage Editor |

As the bus ride jolted to a close, I awoke to find myself in Craigville, Massachusetts, a quaint area of Cape Cod full of marshes, cottages, and windy beaches. Of course, I was not alone on this adventure—Craigville became a temporary haven for me and 66 other juniors as we embarked on the annual Winsor Class VII Retreat. 

From April 13-14, our class stayed on the Cape, with most of our time spent inside the Lodge, a large, airy cottage that served as our main meeting place (and, as a nice bonus, where my room was located). Over the course of two packed days, our grade played bonding games, debated scenarios, wrote ourselves letters and, of course, picked our theme for senior year—and yes, I’m sorry to say the rest of Winsor will have to wait until September to find out what we chose.

One of my personal favorite activities was Dolphin, a chaotic game during which one person leaves and then reenters to complete an unknown task (chosen in their absence) with only emphatic “YES”es and “NO”s as clues. Other highlights included a high-energy talent show, some much-needed down time, the occasional walk on the beach, and an impromptu ice-cream party disguised as “45 more minutes of scenarios” that was received with glee. 

As for the results of this trip, I do think we achieved what we set out to do—that is, we satisfied the stereotypical goals of “class bonding” and crafting our senior year. Yes, we planned our logistical agenda for next year, but I also managed to talk to people I don’t normally talk to, sing along to nostalgic songs with my whole class, and connect with others in a way I didn’t expect. 

Emma Roffman ’27, one of our class presidents, thought the retreat served as “a really great bonding experience for our class” and shared two personal highlights: “picking our homeroom theme and doing the talent show.”

Ms. Crowley, Winsor’s Learning Specialist and Class VII Dean, mentioned that her personal goal was for our grade to “get thinking about the transition from junior to senior year, where you will be the leaders of the school,” and for students to “think about what kind of leader they want to be.” She added that the aim was also to “bond off campus and get a break from the intensity of classes.” 

Although our retreat was only two days, I agree that the small getaway was a much needed break from the hectic aspects of daily life, while also providing a chance to reflect on our own Winsor journeys thus far and our transition into this final chapter. Besides, who doesn’t enjoy a little seaside vacation, complete with karaoke, raucous games, and some late-night frozen delights?

Class VII at Craigville Retreat Center | Image Source: Ellen Crowley