A rock formation along Route 165 in Voluntown is painted like a dog in this photo taken in 1940. Credit: Library of Congress, Prints & Photographs Division, FSA-OWI Collection.
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In the 1920s, State Highway 165 followed today's Route 94 from Glastonbury Center to Buckingham School, just beyond today's Route 83.
Commissioned in 1932, the modern Route 165 originally extended 11.54 miles, from Route 12 in Norwich to Route 138 in Voluntown. The original route, from west to east:
- 8th Street and Smith Avenue, from Route 12 to Hamilton Avenue
- Long Society Road, eastward to Shetucket Turnpike
- Shetucket Turnpike, eastward to Old Shetucket Turnpike (which was likely just "Shetucket Turnpike")
- Old Shetucket Turnpike, to Preston Plains Rd
- Preston Plains Road (now Route 164) to today's Route 165
- current Route 165 to Church Street in Voluntown (Route 138A starting in 1935)
Correspondence in 1938 had the western terminus of Route 165 at the Norwich city line.
Changes - Voluntown to Rhode Island
At the time, the Beach Pond Road segment of today's Route 165 heading to Rhode Island from Voluntown was actually part of Route 138.
In 1938, Route 138 was moved from Beach Pond Road to Rockville Road, where it is today. Beach Pond Road became unsigned SR 420.
In 1947, Route 165 was extended eastward along SR 420 into Rhode Island. Also, its western end was removed from the 8th Street connector to Route 12, and moved to the intersection of Hamilton Avenue with Route 2.
Changes - Norwich to Preston
In 1949, an act was submitted to the state house asking for Hamilton Avenue, between Route 2 and Smith Avenue (where Route 165 turned at the time) to the state highway system. In 1952, Route 165 was redefined to follow Hamilton Avenue from a new start at Route 2.
In 1960, a section of Route 165 in Norwich and Preston was relocated slightly to the north. Long Society Road, the old alignment, became SR 519 in 1960, but was turned over to the towns in 1962.
Changes - Preston City
In 1939, Route 165 and Shetucket Turnpike were relocated to the north, to cross Route 164 in place of the short overlap. The old route, Old Shetucket Turnpike, became SR 443. It was turned over to the town in 1962. (Locally, and unofficially, the road is called Route 165A.)
