The opening days of school at OES are devoted to a series of orientation activities. Boarding students report to school just before Labor Day for dorm orientation. In general, school officially begins for everyone on the Wednesday after Labor Day.

At the beginning of the year, each class has a group experience. The Freshmen focus on getting to know each other and travel to an off-campus location for two nights; the Sophomores journey into Wilderness Areas of Oregon and Washington for a four-day backpacking experience; the Juniors participate in College Decisions; the Seniors retreat to offer service to the community and to look at their roles as leaders in the School.