Raymond Hill, South Pasadena

Why you should experience Raymond Hill in Los Angeles, California.

Raymond Hill is a storied enclave where the West San Gabriel Valley's residential character meets elevated terrain, resort-era origins and a concentrated collection of postwar hillside housing overlooking the Arroyo Seco corridor.

Positioned between South Arroyo, Madison Heights, and Central South Pasadena, the neighborhood occupies a prominent rise extending through Raymond Hill Road, Fair Oaks Avenue and Columbia Street above the low ground separating Pasadena from South Pasadena. Winding streets climb steeply toward the crest, where mature trees, retaining walls and closely spaced residences follow contours markedly different from the regular grids below. Movement across Raymond Hill alternates between older houses along its approaches and compact apartment courts occupying elevated parcels with broad views toward Pasadena and the San Gabriel Mountains. Descending streets reconnect the hill with Fair Oaks Avenue and the surrounding residential districts, making changes in elevation unusually conspicuous across a geographically small neighborhood. The result is a neighborhood whose steep approaches, layered housing and commanding position preserve the physical imprint of a hill that has repeatedly been remade.

What you should know about Raymond Hill.

Raymond Hill is best known for the Raymond Hotel, the resort that transformed the former Bacon Hill into one of Southern California's defining destinations during the first great wave of winter travel from the eastern United States. Boston travel entrepreneur Walter Raymond began planning the venture in 1883 and selected the isolated granite hilltop for the views it commanded across surrounding orchards toward the San Gabriel Mountains. Excavating the summit proved unexpectedly difficult, with granite blasting driving construction costs beyond Raymond's original expectations before his father Emmons Raymond helped finance completion. The Los Angeles and San Gabriel Valley Railroad supported the enterprise with a depot at the foot of the hill, giving arriving travelers direct access to a resort otherwise separated from the young communities around it. The Raymond opened in 1886 with 200 rooms and became the San Gabriel Valley's first major resort hotel, drawing affluent winter residents from the Midwest and East during nine successful seasons. An ember from one of its eighty chimneys ignited the wood-shingle roof on Easter Sunday in 1895, destroying the building. Walter Raymond reopened a substantially larger hotel in 1901, adding hundreds of rooms, formal gardens, golf grounds and an underground passage from the Fair Oaks Avenue arrival point to an elevator ascending toward the lobby. The rebuilt resort survived for three decades before financial pressure during the Great Depression led to foreclosure in 1931 and demolition in 1934, leaving the hill available for an entirely different form of development.

Postwar housing recast the summit through a concentrated apartment project tied to developer Paul Trousdale, whose later work would spread across some of metropolitan Los Angeles's most prominent residential districts. Trousdale subdivided thirty-six Raymond Hill properties in 1945 for four-unit apartment buildings, introducing a compact multifamily pattern onto ground that had supported the former resort. The early buildings resembled large detached houses, allowing four residences to occupy each property without adopting the massing of conventional apartment blocks. A 1949 advertisement placed Trousdale and Associates' South Pasadena holdings at a value of $1.152 million as the developer simultaneously expanded an organization responsible for thousands of Southern California houses. The investor syndicate owning the Raymond Hill Apartments placed all thirty-six buildings on the market individually in 1951, and the entire group had transferred to buyers by 1953. Mid-century construction continued nearby as apartment architecture grew more explicitly modern, culminating in Edward H. Fickett's 1954 Fireside Manor Lanai Apartments on Amberwood Drive. Fickett, whose postwar career encompassed tens of thousands of Southern California residences, designed the forty-unit complex with expansive glazing, a sweeping roof profile, lightweight balcony fronts and an interior court organized around a pool. Raymond Hill consequently compresses two radically different periods of Southern California development onto the same summit, with an elite winter resort displaced by apartment housing conceived for the enormous residential demand of the postwar metropolis.

How to fold Raymond Hill into your trip.

Raymond Hill works as the anchor for a daytime outing connecting a major collection of European and Asian art, a preserved assembly of nineteenth-century Los Angeles buildings and a Mediterranean garden created on land once reserved for a freeway project.

Begin at Norton Simon Museum, whose institutional ancestry reaches to the Pasadena Art Institute founded in 1922 and incorporated two years later. The organization acquired 9.5 acres at Carmelita Park before becoming the Pasadena Art Museum in 1954 and emerging as an important center for twentieth-century art. Ladd & Kelsey designed its 85,000-square-foot building, opened in 1969 with 115,000 exterior tiles created by Edith Heath. Construction debt threatened the museum during the early 1970s, and industrialist Norton Simon assumed its financial obligations and management in 1974 as his private holdings of European painting and South and Southeast Asian sculpture sought a permanent home. Simon had acquired more than 8,000 works during his lifetime, including major holdings by Degas and paintings by Rembrandt, Van Gogh and other European masters. The combined institution reopened in March 1975 and adopted the Norton Simon name that October, with Frank Gehry later directing a major interior renovation between 1996 and 1999. Continue to Heritage Square Museum, created in 1969 as Los Angeles redevelopment threatened surviving Victorian-era buildings across older neighborhoods. Eight significant structures were eventually relocated to the five-acre site, allowing houses, a church, a railroad depot and other buildings constructed during Southern California's first century of statehood to survive together. The collection ranges from the Longfellow-Hastings Octagon House to the elaborate William Perry House and includes the Palms Depot, Lincoln Avenue Methodist Church, Hale House and Valley Knudsen House. A 1909 Denver & Rio Grande Railroad boxcar extends the assemblage beyond domestic architecture into the transportation history that accompanied metropolitan growth. Conclude at Arlington Garden, where Betty and Charles McKenney transformed a vacant three-acre property into a Mediterranean garden beginning in 2005. Caltrans had acquired the ground for the proposed 710 freeway, and the property remained a compacted vacant lot after that project stalled. Pasadena councilmember Steve Madison approached community members in 2002 about a future use, leading the McKenneys to work with designer Mayita Dinos on a garden suited to Southern California's dry climate. Dinos retained mature palms, oaks, a jacaranda and a pepper tree surviving from an earlier mansion property and drew inspiration from Mediterranean planting traditions. Initial planting began during the summer of 2005, gradually converting transportation reserve land into a three-acre collection supporting birds, bees and butterflies amid dense urban surroundings. The progression moves from an internationally significant art collection through relocated architecture from nineteenth-century Los Angeles and culminates in the conversion of abandoned transportation ground into a carefully composed Mediterranean garden.

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