
Photo courtesy of @ea1785
Each fall, the Episcopal Academy’s freshmen begin their Upper School journey far from campus at Outward Bound. During their five days in the wilderness, they have to hike, camp, and cook alongside a small crew of classmates. For the class of 2030, the trip offered an early insight into what high school has to offer: new challenges, new friendships, and a chance to come together as a grade.
According to III Form Dean and Upper School counselor Caroline Graham, the trip has a deeper (continued from p. 1) meaning than simply spending time outdoors. “I think the larger purpose is really to expose all of our Upper School students to the idea that they can overcome hard things,” she states. This message can be applied to new Upper School experiences such as heavy workloads or grueling sports practices.
For many freshmen, Outward Bound was unlike anything they had experienced before. Leighton Harfst ’30 admits she is not much of a camper, but the trip turned out differently than she expected. Her crew made dinner in the woods for the first time, and even had backcountry cake to celebrate their counselor’s birthday. “Outward Bound is definitely physically and mentally challenging,” she says, “but to push through, you just need a good mindset.”
Henry Pennay ’30, who had backpacked before, still found the week demanding. “The hikes were hot, long, and tiring, and two major rainstorms made things even tougher. One storm hit in the middle of the night.” But even so, Pennay describes the trip as a “positive learning experience overall.”
Often, the most challenging moments brought the crews closer together. For Ella Christie ’30, the most memorable moment was reaching the top of Bee Mountain, the tallest climb of the trip. “Our backs were hurting from the bags, and we were all exhausted,” she says. “Our team worked together to encourage each other, and when we made it to the top, we all felt so proud of each other and ourselves.” Moments like this showed freshmen that challenges feel a lot more manageable when they are shared.
Harfst shares a similar lesson from the toughest hikes: “When a hike became tiring, we kept pushing ourselves to go further.” She explains, “Once you are [done with] that mountain, it is so rewarding.”
The groups also supported each other through individual challenges. A big challenge in Outward Bound is the solo time, a period where students spend time alone in the woods, testing their ability to reflect on themselves and be comfortable being bored. Christie reminisces about how her solo time pushed her out of her comfort zone, and how her crew made sure she knew how proud they were of her when she finished. “I learned that there is so much I am capable of,” she says. “I just have to put my mind to it.”
In addition to teambuilding, the faculty’s support and planning take time and effort. “As deans and faculty, we really try to be intentional about these students and create crews randomly, but also intentionally, so that they can know and grow with their peers in this shared experience,” Graham explains.
This approach makes a positive difference for incoming students to Episcopal. After five days of hiking, cooking, and camping together, crews learn how to work as a team and adapt as a group. “By the end of Outward Bound, you knew everyone so well, it was hard to tell who was new and who had been there forever,” Christie says. Pennay saw the same thing in his crew. “Our whole group really bonded, and there were some unlikely friendships,” he says.

Photo courtesy of @ea1785
These friendships followed the freshman back to campus, along with a new sense of confidence. “If I was able to be in the wilderness for five days, then I can surely complete high school,” Christie says. “I am forever grateful for the relationships and memories I built,” she adds.
Graham hopes that these lessons stay with freshmen long after they return to campus. “Sometimes the only way out is through,” she says. Whether it is a tough test, a hard practice, or a busy week, the Class of 2030 is learning that difficult moments do not last forever and can be overcome with a positive attitude.
As freshmen settle into life in the Upper School, Outward Bound remains a shared starting point for the entire grade, whether students are new to EA or have been a member of the community since Lower School. The experience gives them a crew in the mountains and the hallways, a sense of belonging, and the confidence to take on the next four years of their high school career.