Hillside in Northwest Portland is an urban neighborhood with small-town charm. Bordered by Forest Park to the north, and Burnside to the south, Hillside is only a hop, skip and a jump away from the Alphabet District and its iconic restaurants and shops. Yet the neighbors know each other by name and can often be found playing pickleball together or walking their dogs on the lawn in front of Hillside Community Center. The center is the heart of this small, forested community, a gathering hub where many of the neighborhood children attend Pipster Prep Preschool. Though small, the neighborhood packs a punch. A few steps north and you’re in the woods. A few steps east, and you’re in the city.
What Neighbors Say
Tamara Pellicier says Hillside was a godsend during the pandemic. “We walk a flight of stairs, cross the street, and we’re in the forest,” she says. During quarantine, she took “forest baths” every day with her wife, Stacy Drasen, and their children Clea, age 11, and Axel, age 6. Pellicier teaches at Catlin Gabel School, and Drasen is a pediatrician in Vancouver — both say their commutes are a breeze, giving them more time to enjoy life in Hillside. They also love that the neighborhood goes all out for Halloween, where over-the-top decorations and full-size candy bar treats are the standard. They acknowledge that the neighborhood is expensive, but despite the elegant homes, they say Hillside remains down-to-earth, friendly and a fantastic place for families.
Hillside Community Center boasts tennis and basketball courts, a gymnasium, a rock climbing wall, a soccer field and playground. It is the realized dream of Hillside neighbors, 12 of whom took out second mortgages on their homes to secure the gathering space in the 1970s, before officially turning it over to the City of Portland. Kids will also love hiking to the “Witch’s Castle,” in Macleay Park (pictured above), or seeing the spectacular views from historic Pittock Mansion. Fans of Wildwood by Colin Meloy will love living in the real-life setting of the children’s novel.
While there are no restaurants within the borders of Hillside, neighbors often walk to Northwest 23rd Avenue for local eats. The vegetarian curry at Boxer Ramen is bursting with umami flavor, and Salt & Straw’s rotating menu of seasonal, made-from-scratch ice cream is always a family favorite. Papa Haydn, a Portland staple since 1978, offers both dine-in and takeout options, with an extensive and famed pastry case. From casual eats to fine dining, the very best of the Portland foodie scene is Hillside-adjacent.
To read about more fun neighborhoods like this one, check out the rest of our Neighborhood Guide.