Jessie’s Oak

As you wind your way along the gentle curves of Glenbrook's long driveway, past the old hay shed, your eyes are drawn to the graceful canopy of Jessie's Oak. This magnificent English Oak tree has stood for generations, its branches a quiet marker of everything that has passed beneath them.

Jessie's Oak is named after Jessie True (née Chudleigh), the third child of Glanville Chudleigh, the founder of Glenbrook, who left the farm in the early 1920s to pursue her dream of becoming a nurse in Sydney.

During her time in the city, Jessie attended the anniversary celebrations of Anthony Hordern & Sons, a grand department store that was, in its day, the largest in the world, located on the site now known as World Square. Fitting for this story, the store's emblem was a mature oak tree and their motto was "While I live, I'll grow." The store marked its anniversary by giving away commemorative oak saplings to customers. Jessie brought one of these tiny trees back to Glenbrook and planted it along the driveway.

The oak's early years were far from easy. As Ken, Jessie's nephew and the next generation to tend the property, recalls, curious cows repeatedly nibbled the young tree, stunting its growth. It was not until the mid-1940s, when Ken built a tall tree guard, that the oak was finally able to grow undisturbed. His care paid off, and decades later Jessie's Oak has flourished into the grand tree we see today, with branches stretching more than 30 metres across.

For us, Jessie's Oak is more than a tree. It is a living link to our family's past, a symbol of resilience, and a beautiful welcome for all who arrive at Glenbrook.