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To the motorist, Route 39 begins where seven other highways intersect: SR 841, Route 37, Route 53, and the state's only four-way overlap: I-84, US 6, US 7, and US 202.
Route 39 not only intersects, but crosses Route 37 twice. No two other state highways cross twice.
Also, at New Fairfield Center, where 37 and 39 cross, there are two short side streets called Old Route 37 and Old Route 39.
In Afghanistan, 39 is considered unlucky – and not because of one of its famous divisors.
Commissioned in 1932, Route 39 originally extended about 13.6 miles from Route 55 in Sherman to Route 37 in New Fairfield center. South of there, the road to Danbury was called Route 100.
In 1934, Route 37A was created, taking over most of Route 100; and Route 39 was extended along Ball Pond Road and Milltown Road to the New York state line, for a length of 18.61 miles. The Milltown Road portion, which had not been part of Route 100, was formerly unsigned SR 464.
On Mar. 29, 1963, Route 37A was deleted. Route 39 was rerouted and extended over most of Route 37A to Danbury. The leftover portion of old Route 39 (Milltown Road), long ago SR 464, became SR 839.
One more note: the Edwards and Kelcey recommendations to the state during the 1961 road reclassification effort included rerouting Route 39 from Ball Pond Road to Gillotti Road (town-maintained) – about a 1.1-mile shortcut. The state retained the Ball Pond Road alignment.
The town of Sherman website includes the text of the following state public act:
"AN ACT INCLUDING A HIGHWAY IN THE TOWN OF SHERMAN IN THE TRUNK LINE SYSTEM.
"Be it enacted by the Senate and House of Representatives in General Assembly convened:
"The road commencing at the second district school house on route number 39 in the town of Sherman and extending westerly to the New York state line is included in the trunk line system of highways and shall be maintained by the highway commissioner.
Approved, June 20, 1939."