Nestled just northwest of downtown Portland, the Hillside neighborhood is a verdant, peaceful enclave with a past as rich as the panoramic views it offers. Known for its winding streets, historic homes, and canopied parks, Hillside has fostered a quiet, close-knit community for over a century. Whether you’re wandering through leafy streets like NW Macleay Boulevard or enjoying a sunset in Wallace Park, Hillside’s history is as much a part of the neighborhood as its Douglas firs and rhododendrons.
The Origins of Hillside
The story of Hillside begins in the late 19th century, as Portland’s population boomed and the city expanded into the lush forests that skirted the Willamette River’s west bank. The steep slopes and dense woods west of downtown were once considered too remote for residential development; however, by the 1890s, Portlanders seeking respite from the increasingly crowded city center found Hillside’s elevated terrain an appealing retreat.
Early records show the neighborhood’s boundaries taking shape in the area between NW 23rd Avenue and the forested slopes that rise west into Forest Park, encompassing the present-day Hillside and portions of Kings Heights. The area’s steep topography inspired its eventual name—“Hillside”—a fitting moniker for a community perched on the slopes above the city, offering sweeping vistas of Portland and the distant Cascades.
Naming the Neighborhood: Hillside’s High Ground
Before its official designation, residents and developers sometimes referred to the area as “Westover” or “Macleay Heights,” but the name “Hillside” quickly took root. The name was a natural choice: the neighborhood’s steep inclines, winding streets, and dramatic elevation changes defined daily life—and the very character—of the area.
The name became widely recognized in the early 20th century as the city extended its streetcar lines, making Hillside more accessible. These new routes encouraged development that gradually transformed the wooded hills into a vibrant residential neighborhood, while still retaining much of its natural landscape.
Key Historical Milestones
Hillside’s journey from rugged hillside to beloved neighborhood is marked by a series of milestones:
- Streetcar Expansion: The introduction of the streetcar system in the early 1900s linked Hillside with the rest of Portland and spurred residential growth. The streetcar line up NW Westover Road served as a vital artery for commuters, catalyzing the construction of the area’s iconic Craftsman and Colonial Revival homes.
- The Macleay Estate: Scottish immigrant Donald Macleay played a pivotal role in the neighborhood’s early development. His former estate formed the basis for what is now Macleay Park, one of Hillside’s most cherished green spaces. Macleay’s home, the historic Macleay Mansion at NW Westover and Macleay Boulevards, stands as a testament to the area’s deep roots.
- Hillside Community Center: Built in the 1940s as an elementary school, this mid-century modern building at NW 24th Avenue and NW Kearney Street was repurposed as a community center in the 1970s after the school closed. Today, it serves as a hub for neighborhood events, classes, and gatherings—a reflection of Hillside’s enduring community spirit.
Landmarks That Tell the Story
Hillside is rich in landmarks that narrate pieces of its colorful past:
- Macleay Park: Stretching from NW Upshur Street into the wilds of Forest Park, Macleay Park is a natural oasis named for the influential Macleay family. The park’s hiking trails, including the popular Lower Macleay Trail, wind past Balch Creek and the mysterious “Witch’s Castle,” an evocative stone ruin with its own legends.
- Historic Homes and Architecture: Architectural gems line NW Cumberland Road, NW Marlborough Avenue, and adjacent streets. Many homes, dating to the early 20th century, showcase classic Portland styles—Bungalows, Tudor Revivals, and Mediterranean villas—with stunning gardens that flourish in the mild hillside climate.
- Hillside Community Center: This institution not only anchors the neighborhood but also showcases the community’s resolve to preserve communal spaces and foster neighborhood connections in an ever-changing city.
Evolution Through the Decades
Hillside has changed in step with the city around it, but its core values have remained steady: a reverence for natural beauty, a commitment to community, and a passion for preserving neighborhood identity.
- Early Years: From timbered slopes and small farms to elegant early 20th-century homes, Hillside quickly evolved into a sought-after residential enclave, attracting families, professionals, and artists.
- Mid-Century Growth: The post-war era brought new homes and subdivisions, with careful planning to maintain the area’s natural landscape. The old elementary school became the Hillside Community Center, nurturing the neighborhood’s social fabric.
- Contemporary Hillside: Today, Hillside harmonizes historic homes with newer, eco-conscious designs. Residents remain fiercely protective of the area’s tree canopy, parks, and trails. Local events—from art shows at the Community Center to volunteer ivy pulls in Macleay Park—reflect a neighborhood in tune with both its heritage and its future.
What Makes Hillside Special
Ask any longtime resident, and you’ll hear about more than just the views. You’ll hear about walking to Wallace Park for the annual Slabtown Festival, about the hush that falls over the neighborhood on snow days, or the laughter during community potlucks at the center.
Hillside’s blend of quiet streets, historic charm, and urban proximity is rare. Residents feel connected—not just to each other, but to the thread of Portland history that runs through their neighborhood. Whether it’s the echoes of old streetcars on NW Westover or the lingering scent of cedar in Macleay Park, this sense of place is palpable. Hillside remains, above all, a refuge: rooted in history, shaped by nature, and cherished by generations.