Starting in 1897 and continuing through 1930, Seattle undertook a series of regrades to flatten the city’s terrain. Many of these regrades focused on the Denny Hill. City officials, including City Engineer R.H. Thompson, reasoned that Denny Hill’s steep slope prevented Seattle’s northern expansion from the business core downtown.
In 1898, the Engineering Department took the first steps to address this problem, regrading First Avenue between Pike and Denny Way. The first phase of the Denny Regrade began in 1903 and addressed the area on the western side of 5th Avenue. The first phase lasted 8 years and was completed in 1911. During this period, additional work was done to regrade Jackson Hill (in 1907) and Dearborn (1909-1912).
Between 1929 and 1930, the city completed the remainder of the regrade work on Denny Hill on the eastern side of 5th Avenue. In his autobiography, That Man Thompson, R.H. Thompson stated that over 16 million cubic yards of earth were moved as a result of the combined regrades.
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| The Denny Hotel (later called the Washington Hotel) stands on the south summit of Denny Hill before being torn down, 1905. |
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| Trains move loose earth at the south summit of Denny Hill near the under-construction New Washington Hotel, at the corner of Second Avenue and Stewart Street, 1907. |
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| Third Avenue north of Marion Street is flattened out in the first Denny regrade, 1907. |
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| Looking west down Spring Street during the first Denny regrade, 1907. |
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| Horse teams march up Marion Street, 1907. |
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| Looking south from Third Avenue and Madison Street, 1907. |
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| A few "spite mounds" stand amid the flattened remains of Denny Hill, 1909. |
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| The remains of Denny Hill, 1909. |
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| The remains of Denny Hill, 1909. |
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| 1909 |
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| Denny Hill is slowly washed away by powerful water cannons, ca. 1910. |
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| 1909 |
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| 1909 |
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| Steam shovels dig near the Jose P. Rizal bridge during the Dearborn regrade, 1912. |
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| The Ross Shire Hotel on Sixth Avenue and Marion Street, 1914. |
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| A steam shovel digs on Marion Street during the Sixth Avenue regrade, 1914. |
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| A conveyor belt for moving earth at Fifth Avenue and Battery Street, 1929. |
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| A conveyor belt carries earth from the dig site to the harbor, 1930. |
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| A crowd gathers to witness the last shovel of dirt and the completion of the second Denny regrade, 1930. |