From 1932 to 1951, Route 65 extended 9.66 miles from US 1A (now US 1) in Bridgeport to Route 8 (now Route 110) in Shelton, along what would later become a segment of Route 8. Its path, from south to north, was:
- Noble Ave., from Boston Ave (old US 1A) to Huntington Tpke.
- Huntington Tpke. to Penny Ave.
- A section of 2-lane road leading to Huntington St. which was replaced by the Route 8 freeway
- Bridgeport Ave. and Center St. (now SR 714) to Howe Ave. (old Route 8)
At this time, Route 8 had a similar alignment to today north of Shelton, but followed the west bank of the Housatonic River to end in Stratford while Route 65 continued to Bridgeport (see map at right). This routing dates back to the original New England Interstate Route 8, laid out in 1922. Route 65 was created in 1932 from the old state highway 316.
As plans for a Route 8 freeway emerged in the late 1940s, it was decided to send Route 8 to Bridgeport instead of Stratford. Route 65, in the crosshairs of a very large gun, became part of the relocated Route 8 on Sept. 27, 1951. Route 65A was also renumbered on that date.