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San Jose is a huge and sprawling city of over 900,000 people, covering 175 square miles. Much of that area is given over to suburban style single family detached homes built in the 1950s and 1960s. While that has provided good housing for several generations of families (now increasingly Asian and Latino families) most do not find it esthetically appealing.
Downtown San Jose and the neighborhoods surrounding it have a longer and more complex urban history, and thus more varied architecture. San Jose is actually the oldest European established civil (as opposed to military or religious) settlement in California. The Spanish government established it in 1777 to supply food for nearby missions. The oldest remaining structure--only partially in its historic form--is the Peralta adobe at 184 W. St. John St., built in 1799. The adobe is open for tours.
Cesar Chavez Plaza along Market St. south of San Fernando St. is a portion of the original Spanish plaza in Downtown San Jose. The Plaza is lined with major buildings, as it would have been in the Spanish/Mexican era. There is the small, fine, free San Jose Museum of Art at 110 S. Market St., partially housed in a Romanesque 1892 building built as a post office, and partially in a new addition. Just to the north at San Fernando & Market is St. Joseph’s Cathedral, an 1877 structure which replaced earlier Catholic churches. To the south at 170 S. Market St. is the Fairmont Hotel. Construction of the Fairmont in the early 1990’s signaled San Jose’s "big city" status to many, but others regarded it as a pretentious and out of scale stage set. The Hotel Montgomery (211 S. 1st St.) is south of the Fairmont, but entered off 1st St. The 86 room, four story Montgomery, built in 1911, was moved 186 feet south so that the Fairmont could build an annex.
The west side of the plaza showcases the Tech Museum of Innovation, with its dome and its pop art orange and blue colors (corner of Park & Market Streets). There are also some unfortunate examples of the bland, street-hostile office buildings built in San Jose in the 1960s and 70s, years of downtown decline. Just to the south, across San Carlos St. is the Saint Claire Hotel, which replaced the Montgomery in 1926 as San Jose’s leading hotel (on the other side of Market there is a new Marriott and San Jose’s convention center).
Not all of Downtown’s interesting buildings are found around the plaza. There is a National Register of Historic Places historic district--The San Jose Downtown Commercial District-- in the area roughly bounded by S. First St. to the west, E. San Fernando St. to the south, S. Third St. to the west, and E. Santa Clara St. to the north--see the National Park Service website for more details.
The strategic use of redevelopment in Downtown San Jose has supported the construction of numerous public buildings. One of the most striking is the brand new City Hall, complete with domed City Council chamber, on East Santa Clara St. at 5th St. The City Hall was just returned to Downtown San Jose, after decades of exile in the auto-oriented Civic Center roughly a mile to the north (Santa Clara County buildings remain at the Civic Center). Only a block away, at 4th & San Fernando, is the new Martin Luther King Junior Library. The library is both a public library and the library for San Jose State University--a unique partnership--which is adjacent to the site. This library’s blandness is its virtue, it is generally agreed to function better as a library than the spectacular decade old San Francisco Main Library.
Outside Downtown, a scattering of sites:
Winchester Mystery House -- 525 S. Winchester Blvd. near I-280 -- Undoubtedly San Jose’s most popular architectural attraction, the Winchester Mystery House is a massive Victorian pile. Sarah Winchester, heir to the rifle fortune, obsessed by the guilt of those killed by the Winchester Repeating Rifle was told by a fortune teller that she should continuously build onto the house. Workmen were kept occupied for years, building projects under her direction that made no sense -- stairways and doors leading nowhere, windows opening to walls, and the like. Admission charge.
Santana Row -- Winchester & Stevens Creek -- Just up the road from the Winchester House is Santana Row, a faux Mediterranean mixed-use shopping center with hundreds of condominiums built above it. Built with attractive and inviting public spaces, Santana Row has been a hit with local residents who browse, shop and just hang out.
Hensley Historic District -- Just northeast of downtown, in the area bounded by 2nd St. to the West., 6th St. to the east, Julian St. to the south and Empire St. to the north. This is San Jose’s best grouping of various Victorian style homes, including larger and more elaborates on 3rd St. and smaller workingmen’s homes on 5th St. Two blocks to the north along Jackson St. is the commercial core of Japantown, one of three remaining Japantowns in the country. The other two are in San Francisco and Los Angeles.