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The State of California has undertaken four separate bores through the Berkeley Hills to form the 3,610-foot-long Caldecott Tunnel (originally known as the Broadway Low Level Tunnel). Working with the New Deal Public Works Administration, state engineers made the first two bores between 1934-1937 and yielded a space 14-feet, 10-inches high, with two 11-foot-wide lanes. A third bore undertaken between 1960-1964 created a 3,771-foot-long space, with a 18-foot, 4-inch clearance and room for two, 14-foot-wide lanes. In 01/2012, the state and its main contractor, Tutor-Saliba, began a fourth bore set to cost $402 million. A completion date of late 2013 was envisioned.

A tunnel, known as the "Kennedy Tunnel" predated the Caldecott in roughly the same location, dug between the 1870s-1903. The Oakland and Contra Costa Tunnel Company began work in the 1870s, but went bankrupt, leaving the tunnel unfinished. The project was revived in the 1890s, as funds were collected, and completed in 1903.