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Route 272 is one of a handful of Connecticut signed routes that "dead end" at the state line; over the border, the road is locally maintained. Near Bald Mountain in Norfolk, Route 272 reaches the highest elevation (1,555 feet) of any numbered highway in Connecticut.
Before 1932, the segment between today's Route 4 in Torrington and today's US 44 in Norfolk was called State Highway 312.
On Jan. 1, 1932, SH 312 became Route 49, a number that fit in with other highways (41, 43, 45, 47) in the area.
A short segment of North Street in Norfolk, leading from today's US 44 to the Central New England Railroad near Roughland Road, became SR 701. Traces of the rail line are visible from the air. There was apparently a station or depot there as well.
In 1935, Route 49 was extended to the state line, taking over SR 701, for a length of 18.01 miles (0.05 miles longer than today).
Before World War II, there was talk (local or state, not yet known) of placing a large rotary at the US 44 / Route 272 (formerly 49, then 72) junction at the Norfolk town green. There are no such plans now.
On May 1, 1954, Route 72 was extended from Plymouth to the state line via Torrington, incorporating all of former Route 49. This version of Route 72, extending from Middletown, was 56 miles long.
In 1963, planners in the state highway reclassification decided a long Route 72 was not useful, and truncated it to Route 4 in Harwinton. The old Route 72 north of Route 4 needed a new designation. "Route 49", if under consideration, was no longer available, so this part of old Route 72 got a new, rhyming designation: Route 272.
Route 372 and the original SR 572 were also former alignments of Route 72.
In 1961 and 1962, construction at the Hall Meadow Brook Dam, built in response to the devastating floods of 1955, included relocating 2.2 miles of Route 272 (which was Route 72 at the time) to the west. The old alignment passes through John A. Minetto State Park.