Route 69 manages to serve New Haven, Waterbury and Bristol without being the primary route in any of those cities. It is four lanes wide in parts near Interstate 84 in Waterbury; and I eastbound has separate exits for 69 north and south. The southern portion of Route 69, known as the Litchfield Turnpike, was once part of the Straits Turnpike, a mile route from New Haven to Litchfield incorporated in The Turnpike leaves Route 69 in Bethany and veers northwest to intercept Route 63 , which follows the approximate Turnpike alignment to Litchfield.
The Straits Turnpike, named for a gap in Beacon Mountain about 14 miles north of New Haven, was a toll road until about In late , as the state planned its renumbering, Route 69 was originally to continue through Waterbury to end at US 6 in Watertown. Instead, that road became Route Route 69 was commissioned in , and incorporated the earlier state highways numbered , , and Main Street Route 14 at the time in Waterbury:.
In , today's Route 69 continuing to Bristol was called Route The road to Burlington was not numbered. In , concrete was laid on 1. This segment of Carrington Road and New Haven Road replaced the mystery road through the forest near the reservoir. Also in , Route 69 was extended to Route 72 in Bristol, incorporating Route After a short eastbound overlap with E.
Main St, Route 69 followed Wolcott St. This is slightly west of its current alignment leaving Waterbury. The extension increased Route 69's length to Around , Route 69 was moved to 7. Signing of Route 69 here, although official in , might have been arranged with the opening of the new road. Part of Milford Street was already SR These roads would later, in , be added as part of Route Interesting: in , a bill was submitted to turn over Burlington Avenue in Bristol, which had not yet become part of Route 69, back to the city.
I don't know what the SR number was at the time. In or , Route 69 was extended south to Route 10 in New Haven, as part of a triple overlap Routes 63, 67, and This was likely done so that more northwestern towns could follow a single route into New Haven. Route 69 was now In , Route 69 saw several changes.
