History
In the 1920s, the road between the New York state line (towards the hamlet of Webatuck) and the Gaylordsville section of New Milford was designated as a state highway known as Highway 129. The old state highway was renumbered to modern Route 55 as part of the 1932 state highway renumbering. The number 55 was chosen to match New York State Route 55 across the state line, which was also extended north from its original eastern terminus in Pawling to Wingdale (via an overlap with New York State Route 22) and then east through Webatuck to the Connecticut state line.
Read more about this topic: Connecticut Route 55
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