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Much of Harbor Drive, a former a major urban freeway in Portland, Oregon was redeveloped as a park in 1978, now know as the Tom McCall Waterfront Park and is often cited as the first instance of freeway removal in the USA and as a milestone in urban planning. The majority of freeway, which carried U.S. Route 99W along the western shore of the Willamette River in the downtown area between the Steel Bridge and the Riverplace Marina, was demolished in 1974. A short section of the original freeway, a ramp stub from the Hawthorne Bridge, now provides pedestrian and bicycle access ramp to Waterfront Park from First Avenue.
The park is a popular destination for sightseers, picnickers, and joggers, and is a site for major civic events such as the Rose Festival fun center.
Harbor Drive opened in 1943 and was the original route of US 99W (locally called "Highway 99W") into downtown Portland from the south. The highway came from Barbur Boulevard and ran through the downtown area via a couplet on 4th and 6th avenues. US 99W then crossed the Willamette River on the Broadway Bridge towards Interstate Avenue, where it headed north to the Interstate Bridge and the city of Vancouver, Washington.
In 1950, a controlled-access highway, though crude by modern standards, opened and was at least partly known as Harbor Drive. It started with an interchange with Barbur Boulevard, joined the Willamette shore near an interchange with Clay and Market streets, and then ran along the shore to the Steel Bridge. US 99W then crossed the Steel Bridge, and turned north on a controlled-access extension to Interstate Avenue, until it resumed its old routing at an interchange with the Broadway Bridge. It was the first freeway to be completed in Portland, and the only north–south freeway for over a decade.
One block west of Harbor Drive was Front Avenue, then a minor street, and one block west of that was 1st Avenue. Many industrial and commercial buildings, including the Portland Public Market building, were located between Harbor and Front. Harbor Drive connected to the downtown streets, the Hawthorne Bridge and the Morrison Bridge via a series of interchanges.
In 1961, the Baldock Freeway (which at the time extended from Eugene to Tigard) was completed to downtown Portland, and signed as Interstate 5 and (temporarily) as U.S. Route 99. The Baldock Freeway connected with the existing Harbor Drive. In 1966, the Marquam Bridge and the Minnesota Street Freeway were completed, thus making I-5 a contiguous freeway from the California to Washington borders, and making Harbor Drive obsolete as a long-haul thoroughfare.
During this period, there was growing resistance (the freeway revolts) to the construction of additional proposed freeways both in Portland and elsewhere in the USA.
The Olmsted Report (1903) and also the Bennett Plan (1912) had proposed an urban greenway to preserve Willamette riverfront, however the Harbor Drive Freeway restricted pedestrian access to riverfront in 1943 and the Oregon State Highway Department has proposals to extend the Harbor Drive.
Oregon Governor Tom McCall halted expansion and created a task force to study options for replacing Harbor Drive with a public place. The task force recommended closure and conversion to a park. The opening of the Fremont Bridge in 1973, which completed the Interstate 405 resulted in a second Interstate through the downtown area, but usefully resulted in reduced traffic levels on Harbor Drive.
Harbor Drive was permanently closed north of Market Street in May 1974. Construction soon began on a new park, Waterfront Park. In addition, the buildings between Front Avenue and Harbor Drive were demolished, and Front Avenue (since renamed 'Naito Parkway' after Bill Naito, a local businessman and philanthropist) was widened to a boulevard. The park opened in 1978. In 1984, it was renamed Tom McCall Waterfront Park in honor of the former governor.
 Harbor Drive today
The southernmost segment of Harbor Drive still exists, though it is no longer a freeway (several traffic lights have been since constructed, providing access to the Riverplace Marina). If one drives northbound on I-5 towards downtown, and does not take the right exits to remain on I-5 or get onto I-405, one is deposited upon the remnants of Harbor Drive. Few signs identify it as such; the exit signs on the freeway indicate the route leads to Naito Parkway, and directional signs heading south all say "To I-5". One other remnant of Harbor Drive is a ramp stub from the Hawthorne Bridge which is still standing. That ramp is now a pedestrian and bicycle access ramp so one does not have to ride or walk all the way down to First Avenue in order to access Waterfront Park.
As well as created a major recreation facility for the city of Portland, the closure of Harbor Drive is widely considered a significant event in urban planning; the first time a freeway had ever been removed and not replaced. It (along with the subsequent cancellation of Interstate 505 and the Mount Hood Freeway) cemented Portland's reputation as a model of pedestrian- and transit-friendly design. Since the completion of Interstate 205 in the mid 1980s, no new freeways have been built in the city, other than a short realignment of U.S. Route 30 near the Fremont Bridge.
Many other cities in the United States have since demolished freeways as well, and more are considering such action. San Francisco is well known for the (earthquake-assisted) demolition of the Embarcadero Freeway; Boston demolished the elevated portion of Interstate 93 as part of the massive Big Dig project; and Milwaukee removed the Park East Freeway. In addition, Seattle is now considering removal of the Alaskan Way Viaduct along the downtown waterfront.
 See also
- Tom McCall Waterfront Park
- Image of Harbor Drive, viewed from above Hawthorne Bridge
- View of Harbor Drive, looking south
- ORoads: US Route 26 (contains map which shows former route of Harbor Drive)
- Mayer, James (December 11, 2006). "Transit activist is still on the road not taken". The Oregonian.