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Connecting the Community: Sisters

Heather Osgood  |  July 24, 2026

Connecting the Community: Sisters

When my parents left Camp Sherman, they didn't go far — just down the road to Sisters, to a new neighborhood called Tollgate. We lived on Easy Street. I promise I'm not making that up.

Some habits followed me from Camp Sherman — my pony still got me to school sometimes. My elementary school sat at the eastern entrance into town — the building's still there, though it's an administrative office now. You've probably driven past it a hundred times without knowing a piece of me is in it.

My dad worked for Brooks Resources, and some of the ground he helped shape is ground you already know: Black Butte Ranch, Tollgate, and later, projects in Bend. Some mornings, we would swing by The Gallery Restaurant for hot chocolate and a powdered sugar donut on the way to school. It's one of my favorite memories of him — small, ordinary, and exactly the kind of thing you don't know you'll miss until years later.

My parents owned The Paper Place — it closed just this year, after all those decades, which feels like the end of a chapter I didn't know I was still holding onto. My mom taught Jazzercise on top of running the store, because that's the kind of relentless energy she's always had, and seems to have passed along to me.

We moved to Portland when my parents divorced, and I started fourth grade somewhere entirely new. But Sisters never let go of me, and I never really let go of it. Summers were Camp Tamarack, and long stretches on my grandmother's cattle and hay ranch with my cousins — the kind of summers that teach you to work before anyone has to ask you twice. Winters were Hoodoo and Bachelor. In 1994, I was named Sisters Rodeo Queen — following in a small way behind my dad, who'd served as the Rodeo's president back in 1979-80. 

The last year of my father's life, he returned to Sisters. I'll always be grateful for that time with him — walking around town, retracing so much of our past together, stopping for maple bars at Sisters Bakery like no time had passed at all.

Sisters was never just a childhood address. It's the place that kept calling me back, decade after decade, until it became clear it never stopped being home.

When I help a family find their place in Sisters now, I'm not just showing them a listing. I know what it means to belong to this town — the kind of place that holds onto you, if you let it.

Next month: Bend — the town where it all comes full circle.

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