On June 1st, 2026, the Winterbrook Planning team, clients, partners, and friends got together at The Holocene to celebrate exactly 25 years to the day since the firm was founded.

Winterbrook team in the early years

June 1st marked a quarter-century since Greg Winterowd and Tim Brooks first established Winterbrook Planning with a vision for an integrated, thoughtful approach to land use and environmental planning. Twenty-five years later, that vision has grown into a legacy of strengthened communities and resilient natural resource stewardship across Oregon and the Pacific Northwest.

The anniversary party was a wonderful chance to step back from our daily work and look back on the incredible journey that brought us here. Guests caught up over a spectacular spread by Pearl Catering, with delicious hors d’oeuvres for vegans, vegetarians, pescatarians, and meat-eaters alike.

The headliners of the evening came when co-founders Tim Brooks and Greg Winterowd took the floor and spoke to the founding days of the firm. It was a poignant reminder of the enduring partnerships and shared values that have defined our history from day one.

The event brought together founding perspectives, current project collaborators, and the team members, led by Managing Principal Jesse Winterowd since 2018, who are actively driving Winterbrook’s mission into the future.

We want to extend a heartfelt thank you to everyone who joined us to raise a glass, swap stories, and look ahead to the next chapter. Whether you were able to celebrate with us in person or raised a glass from afar, you are a vital part of the Winterbrook story.

Here’s to the next 25 years!