Dessert Circle

Teamwork & Leadership

dessert circle featured

Every evening, on every Overland trip, students and leaders sit down (with a sweet treat, of course) to recap the day and listen to every member of the group reflect on their successes and challenges. At Dessert Circle, a longtime Overland tradition, students and leaders share three things over dessert: high, low, cheers.

As each day is an opportunity to create new memories, we’re always spoiled for choice of a “high of the day.” In my eight years with Overland teen adventure trips, my highs have included conquering difficult climbs, laughs on the trail, and celebratory moments like surprise ice cream cones or sprinkler runs.

Field Studies Tanzania Dessert Circle

We share lows, too — not to dwell on difficult moments, but to recognize the ways we can be even more successful tomorrow and to acknowledge that working together and holding high expectations can lift us out of our lows. Every day has its frustrations, but we don’t let our lows define our Overland experiences.

And, finally, “cheers.” Cheers has always been my favorite part of Dessert Circle; it’s an acknowledgement and thank you to someone else in the group who did a little (or big!) something to brighten your day and support you. When we cheers a peer or leader, we’re showing someone that their contributions to the group don’t go unrecognized. We’re also shifting the focus away from ourselves: at Overland, the group always comes first.

As a leader, Dessert Circle has taken on even more significance for me. My highs are moments that I’ve been especially proud to see my students step up, rise to challenges and put the group before themselves. My lows are teachable moments from the day. My cheers are part of my commitment to meaningfully engage with every student every day.

Northwest Expedition Dessert Circle

Dessert Circle is so important to the leader community that we take it beyond our time on trips. Daily at leader training, among Williamstown staff and even after the summer — in group chats and on social media — leaders share our highs, lows and cheers.

When we take time to reflect on our day and intentionally listen to our peers’ takeaways, too, we share valuable memories of today while also strengthening group community and looking optimistically to tomorrow.

From me to you, cheers.

Teen Summer Adventures Dessert Circle CRM
Canadian Rockies & Montana Dessert Circle

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