Oct 14, 2026
Bend, Oregon
Some towns get discovered. Bend got chosen. People arrive in Central Oregon because of a specific idea of how to live: sun on most days, snow when you want it, a river through town, and a mountain range close enough that a weekday morning can start on a trail. It sits on the dry side of the Cascades, in the high desert, and the contrast with the Willamette Valley on the other side of the range is part of the appeal. Less gray, less drizzle, more blue sky. Yet the snowpack still shows up, and the skiing, the climbing, the paddling, the fishing, and the riding go on through every season. It is a sportsman’s and outdoor enthusiast’s paradise, and it knows it.
A member of a particular family
Bend belongs to a small family of places that organize an entire way of life around their surroundings. Sun Valley, Telluride, and Jackson Hole are its closest relatives. These are destinations, but the best of them are also real communities, where people who could live anywhere decided to live there. That decision shapes everything: the pace, the priorities, and the kinds of institutions that take root. Spend time in any of them and you notice the same thing. The landscape is not scenery. It is the organizing principle.
Cascades Academy
At the center of that picture, out in Tumalo, is Cascades Academy, a preschool through twelfth grade day school that we have had the pleasure of working with. It is a world-class institution inside a world-class environment, and the two reinforce each other.
The context is the first thing you notice. The campus has an abundance of open space, and it is housed in a modern, mountain-style architecture that is approaching its 25th year. The school builds its program on that setting, with a real emphasis on outdoor learning and leadership, alongside innovation and STEM. Students are not taken outside as an enrichment activity. The outdoors is part of how the school thinks about learning.
A courageous, strategic choice
What sets Cascades apart in Central Oregon goes beyond its setting. It was one of the first schools in Oregon, if not the first, to join the Mastery Transcript Consortium and adopt the Mastery Transcript. That was a courageous move, and a strategic one. Moving away from the traditional transcript is a risk for any school, because it asks colleges and families to evaluate students on terms they did not set. Cascades made that choice because it was committed to real-world learning, and a transcript that reflects what students can actually do fits a school whose classroom extends well beyond its walls.
Why it fits
I keep coming back to the same observation when I work with schools in places like this. The strongest ones do not fight their context. They build into it. Cascades Academy has done that in Bend: a school as willing to innovate as the community around it is to be outside, and one that treats place, purpose, and practice as a single idea.