Rising up along the banks of the Willamette River, the Portland area was inhabited by the Chinook peoples for centuries before the Oregon Trail opened it up to European-American settlement. Today, it’s one of the 30 largest cities in the United States, with a reputation for thoughtful urban planning, including its height restrictions enacted to protect views of nearby Mount Hood. The best buildings in the city went up long before that limitation, and they’re still around to impress you. These are my favorites.

#1 Pittock Mansion

Portland’s Washington Park, a 410-acre hilly swatch of green, ranks as one of the world’s best urban parks. With its acres of wild forest and miles of hiking trails, the park makes you feel like you’re far from civilization, but, in fact, you’re just a couple of miles from the heart of the city. I spent plenty of time here, at the Oregon Zoo (the oldest zoo west of the Mississippi), the Vietnam Veterans of Oregon Memorial, one of the world’s best rose gardens, and one of the world’s best Japanese gardens. As if those highlights weren’t reason enough to visit, the park is also home to Portland’s most beautiful building, Pittock Mansion, one of the best house museums in North America. Set on 46 lush acres 1,000’ above sea level, the 16,000-square-foot mansion sports some fine views of the city. Built of sandstone in 1914 for Henry Pittock, owner of the still-extant Oregonian and his family, the French chateau–style home features turrets, dormer windows, terraces, and formal gardens, lending the air of a very fine estate. The mansion remained in the Pittock family until 1958 (long after Pittock died in 1919). It remained unsold for a while, and after a historic storm in 1962 damaged roof tiles and window panes, which exposed the interior to water, the owners were ready to demolish the whole thing. Prompted by concerned citizens, the city purchased the property in 1964. Today, the mansion is open to the public. Inside, the grand central staircase of marble invited me to explore the two dozen rooms on three floors. A full restoration complete with fine furnishing brought back the luxuries of the time—a central vacuum system, indirect lighting, an elevator, a walk-in refrigerator, a shower that almost looks like a metal torture device, and “the Annunciator,” an intercom system used to call the servants. The rooms are an eclectic mix of styles—a circular music room; Jacobean, Edwardian, and French Renaissance styles; a Turkish smoking room; the gorgeous library with the quatrefoil ceiling. One visit here makes it easy to understand why it has been listed on the National Register of Historic Places since 1974.

#2 Union Station

The lovely old-fashioned lampposts and the unique bronze Benson Bubbler drinking fountains (where four people can slake their thirst at the same time; see #4, below) line the way up to the impressive Union Station. I could have only imagined how more impressive that station would have been if the original plan, by McKim, Mead & White, had been utilized and what would have been the largest train station in the world had been built. Nevertheless, the current station, opened in 1896, is a delight. It’s the second-oldest operating major passenger terminal in the United States, and by 1922, every railroad passenger train serving the city utilized this station. The asymmetrical building is a mix of Romanesque and Queen Anne architecture and combines straight and curved facades of molded bricks and terra cotta. A deep canopy to keep travelers dry runs along most of the station’s width. Striped awnings shade many of the windows, and red metal tiles cap the entire roof. At the main entryway, a central plaza with an island of local and native plants was added in 2003. Inside, the cool interior features lots of wood, long benches, Italian marble walls and floors, coffered ceilings with rosettes, and 1920s-era phone booths. Of course, the signature piece that I loved the most is the feature that caught my attention originally—the striking 150’-tall tower with clocks on all four sides. In 1948, the tower was embellished with neon signs above the clocks. Two read “Union Station”; the other two convey the simple philosophy of the station itself: “Go By Train.” Placed on the National Register of Historic Places in 1975, Union Station is a charming place to visit, whether you’re going by train or not.

#3 First Congregational Church

Occupying a corner lot along the lovely South Park Blocks—a green mall of elm trees, cast-iron benches, and bronze statues, flanked by two one-way streets and some of the city’s cultural institutions—First Congregational Church has been serving Portland since 1851, although the current church building came along later, completed in 1895. Designed by a Swiss architect to resemble Boston’s Old South Church, the building is regarded as one of the few examples of Venetian Gothic architecture in the United States. The dark stone façade is relieved by a light-and-dark–stone pattern above a band of windows on one side and an arcade of Gothic arches supported by marble columns on the other. The 175’ bell tower is capped with a bright white cupola with fine tracery and a red mansard roof with little dormer windows. Inside, curved pews in the upper gallery give the church a feeling of motion. Part of the ceiling is embellished by cross-like wooden coffers. The stained-glass windows from the early 1900s add color, and an organ that’s often mistaken as original to the church was installed and had its front pipes painted and stenciled only in 2005.

#4 Simon Benson House

I work at a college, but it doesn’t have a separate building for its alumni association. If it did, I would want it to be just like the Simon Benson House. Just a few blocks south of First Congregational Church, Portland State University’s Alumni Association can be found at this remarkable building. Simon Benson, a Norwegian immigrant, found fame and fortune in his new country as a successful logger, innovator, and civic philanthropist. He had this house built in 1901 and remained there until he and his family moved in 1913. After that, the house was turned into a boarding house and then divided into apartments. Added to the National Register of Historic Places in 1983, it thereafter began to fall apart, and the city condemned it in 1991. But more than 1,000 individuals and businesses rallied to save it, and the house was moved from its original location to its current one. Renovation took almost a year, and now PSU’s alumni have a glorious headquarters. The Queen Anne–style house is built of a wood-frame construction. The entrance at the corner leads up to a porch with unique framing. Another porch is off to the side, and a third appears on the upper floor. Windows and rooflines of all sizes and styles add to the house’s unique visual appeal. The interior is awash in rich detail and decoration, each room paneled in a different kind of wood. Benson was fully or partially responsible for building a polytechnic high school, hotels, and the Columbia River Highway; donating the 20 Benson Bubbler water fountains still in use in downtown Portland today; and deeding to the city land that became the Wahkeena Falls Recreation Area (where he paid for the masonry footbridge across the falls), Benson State Park, and Multnomah Falls Recreation Area (where you’ll find the arched pedestrian bridge over the lower Multnomah Falls that he funded). He died shortly before turning 91, having said, “No one has the right to die and not leave something to the public and for the public good.” Fortunately for us, he made good on that word in very tangible ways.

#5 Jackson Tower

Pioneer Courthouse Square, commonly referred to as “Portland’s Living Room,” is a large square in the heart of downtown, with decorative columns and a surface of bricks etched with the names of those who donated $15 to fund its construction. You can come here for chess matches, musical performances at the amphitheater, or the annual Christmas festivities. You’ll also come here to check out Jackson Tower at its southwest corner. Conceived as a white wedding-cake tower, The Oregon Journal Building was completed in 1912. It switched names in 1951, when the Oregon Journal moved out and it adopted the name of the newspaper’s founder. This 12-story Beaux Arts beauty features two setbacks and a three-story clock tower that features four clock faces, one on each side and each measuring 12.5’ in diameter. The exterior is faced with handsome off-white brick and glazed terra cotta. Garlands and a lion’s head occupy the arched space above the main entrance. Keep looking up to note the terra-cotta belt course, cornice, dentils, elaborately sculptured panels, cartouches, and columns. For a special treat, make sure to visit at night, when 1,800 light bulbs screwed directly into the façade illuminate the building after dark.

Five Runners-Up

• New Market Block (1872)
• The Old Church (1862)
• City Hall (1895)
• St. James Lutheran Church (1908)
• Former Portland Public Theater (1928)

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