In May 1756, a committee was appointed to lay out a highway in Colebrook with a six-rod (99 foot) right of way. It was constructed in 1763 with the designation "Highway Number 3" (though not signposted that way), with the intent of facilitating troop movements from Connecticut into the Albany area during the French and Indian Wars.
In 1801, the Waterbury River Turnpike was chartered from the Massachusetts border south, roughly along Colebrook Road and Millbrook Road. In 1850 that corporation dissolved, and Sandisfield Road, as it was known, returned to the town of Colebrook.
In 1845, the section of Colebrook Road leading from Millbrook Road to the Winchester town line was built, completing the alignment of what would eventually become Route 183 in Colebrook.
In the 1920s, old "Highway Number 3" received state designations: state highways 174 and 314. As state aid roads, their improvements were partially funded by the towns.
In 1926, a Colebrook lawmaker succeeded in having the road become a trunk line route to the Massachusetts state line; both states proceeded to improve the route as a third road through the Berkshire mountains. The improved access led to a small real estate boom along the road.
Today's Route 183 was commissioned as an 8.75-mile route in 1932, from US 44 in Winchester to the state line in Norfolk. The Torringford Street segment, east of Route 8, was originally locally maintained, before becoming an unsigned state route (SR 710) in 1943.
The Massachusetts segment of Route 183 was also created in 1932, with the intent to connect with its neighbor. At the beginning, it extended only from US 7 in Great Barrington to US 7 (now MA 7A) in Lenox. The Bay State and Nutmeg State versions remained 18 miles apart, until Massachusetts signed its segment later.
In 1954, in Connecticut, Route 183 was extended south along US 44 and SR 710 to today's Route 4; this might have been done at the same time Route 72 was extended in the area, on May 1, 1954.
In 1959, the Route 183 corridor was contemplated by Massachusetts officials as a new location for a relocated Route 8, which would be displaced by a planned dam in Colebrook.
The original stone-and-mortar Colebrook Bridge over Center Brook, dating back to 1784, was widened in the late 1980s. Instead of discarding the old stonework, they took it apart and replaced it on the outside of the new structure. This idea earned the state DOT an Award of Merit in Historic Preservation And/Or Cultural Enhancement in 1990.
