Never constructed to its full length, the parkway was opened on August 13, 1932 from Westchester Avenue to the city of White Plains.

After an southbound-only interchange with Orchard Street, the Central Westchester Parkway turns northward through North White Plains, paralleling NY 22.

[10] This first section of the Central Westchester Parkway opened on August 13, 1932, with a celebration headlined by a ribbon cutting with White Plains mayor Chauncey Griffin.

The parkway segment cost $1 million (1932 USD) to construct and the ribbon was placed at the location of George Washington's first defensive line in 1776 during the Battle of White Plains.

[14] After several disputes over alignment delayed the project, the state of New York announced the opening of bids on the first segment of the brand new Cross Westchester Expressway on November 23, 1956, which would start on December 20.

The expressway would also boast 10.52 miles (16.93 km) of access roads along with the six mainline lanes and a center median.

[17] Meanwhile, in October 1959, the state of New York announced that the Cross Westchester Expressway would be finished possibly eight months earlier than expected, with a slated completion date of December 1, 1960, although the contract for the Elmsford section would allow it to go until April 1961.

[18] However, in May 1960, the nine-mile-long (14 km) stretch of the Cross Westchester Expressway was announced to open between the Greenburgh–White Plains line and the New England Thruway in Rye in July.

The new bypass also included pieces of Westchester Avenue, which were rebuilt and opened to help get commuters from North Castle to Port Chester, paralleling the new expressway.