Exploring the Hillsdale Neighborhood / by Chris Bonner

Hillsdale Boundary Map.jpg

Homesteaders from Germany, Italy, and Switzerland moved to the Southwest hills starting in 1850. Within a few years, they had cleared larger forests and begun to operate vegetable farms and dairies, supplying the growing City of Portland with fresh produce and dairy. The route they traveled to transport goods to Portland markets became Slavin Road (named for one of the first homesteaders, John Addison Slavin).

In the early 1900s, bright red passenger trains began servicing the West Hills; this meant an influx of urban families to Hillsdale. The neighborhood became more of a market for farmers to sell produce and a spot for residents from surrounding areas (Portland, the Willamette Valley, and Tualatin) to visit. By the 1930s travel was transitioning from rail to automobile and the rail line and portions of the Red Electric route servicing Hillsdale became Bertha Boulevard.

Post World War II, Portland expanded into Hillsdale and much of the active farmland was sold off to provide space for the town’s expanding infrastructure. The Hillsdale Town Center, Wilson High School, and the central commercial district are all built on land that used to be Fulton Park Dairy, which closed in 1953.

Today the Hillsdale neighborhood offers a mix of hilly streets lined with tall trees, some of which have no sidewalks, giving the area a rural feel.


There are three public schools in Hillsdale. Mary Rieke Elementary and Wilson High School are both adjacent to the central business district. Robert Gray Middle School is a short distance away, next to Hillsdale City Park with sprawling greenery, an off-leash dog area, and some picnic tables.

Hillsdale’s close proximity to Oregon Health Sciences University and downtown Portland is a plus. Hillsdale has easy access to 1-5 and mass transit. A great feature of the Hillsdale neighborhood is an extensive pedestrian trails program.

Southwest Trails Group is a community group who promote walking and biking in Southwest Portland. They organize group hikes and bike rides. (Portland's Department of Transportation also offers free maps for walking and biking in the SW). They also build and maintain trails throughout Southwest Portland. The Red Electric Trail–following the route of the old passenger train of the same name–runs through Hillsdale and provide a flat and easy connection from Washington County to the South Waterfront for walkers and bikers. The SW Trails Group is still hard at work on continued development of the Red Electric Trail and other projects.

Points of Interest

George Himes City Park is a forested gem with trails that can take you from the Willamette River to slopes in the west hills where you can catch a glimpse of Mount Hood.

The Hillsdale Library has a LEED Gold certification for meeting a number of “Green” design elements in its 2004 remodel. There are numerous community programs offered at the library ranging from Toddler Storytime to presentations about Portland’s history.

Wilson Pool boasts two outdoor pools open during the summer months: 6-lane lap pool with diving board and family leisure pool with current channel, vortex, tot slide, water slide, and zero-depth water play structure.


Hillsdale is one of thirteen regionally defined town centers in the Portland Metropolitan area and has a thriving commercial center and community. This is in large part to the Hillsdale Business & Professional Association, the Hillsdale Alliance, the Hillsdale Working Group, Portland Public Schools, and numerous community stakeholders. The HBPA focuses their time and resources on continually growing Hillsdale and their urban growth center. The HBPA focuses on community building and planning, traffic, schools, marketing and pedestrian safety. One of the HBPA’s largest successes has been the thriving Hillsdale Farmers Market. They have also succeeded in planting street trees and new sidewalks.

Hillsdale has a variety of great restaurants and businesses; all clustered around the central business district. Oak & Olive focuses on Italian classics like pizza and pasta. Sasquatch Brewing is a great place where family and friends can enjoy a pint of beer and a hearty pub fare. Verde Cocina offers fresh, accessible Mexican food with locally-sourced ingredients.

Gigi’s Café is a great example of the magic that can come from a modest food cart; the brick and mortar location in Hillsdale’s center has been a great success with the breakfast & brunch crowds since they opened in 2014. The Baker & Spice Bakery makes everything from scratch and offers hand-rolled hearth-baked bread, pastries, and cakes in addition to savory options like soups, salads, and sandwiches for lunch.

There is no shortage of adventures you can have wandering around the trails of Hillsdale and rewarding yourself with a delicious meal at one of the local eateries.