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. larger photo

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 (current Route 165) to Route 138

At the time, the Beach Pond Road segment of today's Route 165 heading to Rhode Island 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.

In 1960, a section of Route 165 in Norwich and Preston was relocated slightly to the north. Long Society Rd. is the old alignment.