Route Numbering and Location
US 44 was not one of the original US routes in Connecticut (US 1, US 5, US 6 and US 7), as its out-of-place number implies. It was commissioned on March 1, 1935 (along with US 202) to encourage tourism.
The western half (between Hartford and Canaan) was originally part of a cross-state NE-17; the small part west of US 7 was state highway 121 (1923-1932) and CT 199 (until 1934). Between 1932 and 1934, all of US 44 east of US 7 was part of a long Route 101.
In 1935, US 44 inherited most of the Route 101 alignment. West of Hartford, that's most where it remains today; eastward, there have been some changes.
In East Hartford, US 44 eastbound originally turned south, not north, on Main Street, then followed Silver Lane into Manchester, met up again with US 6, and then went through Bolton Notch, Coventry, Mansfield Depot, and Willington. In 1943, shortly after the Charter Oak Bridge opened, the state decided to place US 6 on Silver Lane and move US 44 to its current alignment on Burnside Avenue.
As the Wilbur Cross Highway was upgraded toward Union in the early 1950s, US 44 was rerouted between Manchester and Willington; the new alignment followed Route 15 (now I-84) from US 6 in Manchester to the Route 74 interchange in Tolland. There, US 44 left Route 15 and followed present-day Route 74 to the 74/44 intersection. The old portion of US 44 through Bolton and Coventry became US 44A.
On Dec. 1, 1982, all this was undone: US 44A was deleted, US 44 moved back, and Route 74 re-extended; US 44 and Route 74 returned to their early 1940s alignments.
Freeway plans - Hartford area
In the early 1950s, a relocated US 44 expressway was proposed, passing from West Hartford to East Hartford near the Bloomfield and Windsor town lines, and using a new bridge across the Connecticut River. It would be the northernmost of the east-west expressways planned for the immediate Hartford area. Connections to other expressways would include the proposed Woods River Expressway (Route 189, since cancelled), the North Meadows Expressway (today's I-91), and probably a US 5 relocation east of the river.
By the late 1950s, the state was instead planning Interstate 291, whose corridor would have been a few miles north of the US 44 proposal. This segment of I-291 encountered fierce opposition circa 1970 and did not survive.
Freeway plans - Northwest Connecticut
In 1956, Connecticut attempted to have the US 44 corridor west of Hartford added to the interstate system; though this was turned down, the state proceeded with planning an expressway there in the 1960s.
In 1963, the state proposed a four-to-six lane expressway leading from I-291 to North Canaan, slated sometime after 1975. In 1966, this was added to the state's highway needs list. The first 5.6 miles, from West Hartford to Simsbury, were on the priority list. A $75 million section to Canton would start by 1975, and the remaining 26 miles (about $90 million) would start sometime thereafter.
In late 1967, highway officials were planning to get funding for a portion of relocated US 44 by about 1972. This segment would lead from I-291 to a point on present-day US 44 near Route 167.
Because the expressway would start with a planned interchange with I-291 in the reservoir areas of West Hartford, US 44 plans were somewhat dependent on the controversial I-291 plans. In 1970, the state decided not to build US 44 over the reservoir, and debated dropping the planned tunnel through Avon Mountain as well.
In 1973, Gov. Meskill cancelled the project in favor of mass transit for the northwest corridor -- but Avon, Simsbury, and Canton have proven too lightly populated for public mass transit.
In 1975, however, the state's 1975 Master Transportation Plan called for allocating $133 million for "studies" of the corridor, from West Hartford to North Canaan.
Other US 44 corridor plans
The freeway plan for US 44 has been abandoned, but other proposals to ease traffic in the Farmington Valley have been considered.
A 1997 plan called for two new highways, north and south of US 44. The north road would be two lanes, connecting Bloomfield, Avon, and Route 10 in Simsbury. The tunnel at Avon Mountain would make this road relatively expensive: $500 million.
The south road would extend from I-84 at Route 9 (the four-level stack interchange) as a four-lane highway, then narrow to two lanes and meet US 44 in Avon. A similar proposal a $118 million four-lane road from the stack to Talcott Notch Road was cancelled in 1998 because of environmental and residential obstacles.
Alternative proposals were not quite as interesting: a median strip on US 44, and additional left-turn lanes. Construction on the two new roads, if approved, would not have started for about five years.
Other relocations and improvements
There are short streets named "Old Route 44" in Abington (west of Route 97) and Eastford (east of Route 198), suggesting earlier reroutings, but I don't have any information yet.
The Y-interchange at Bolton Notch where US 6 and 44 separate was built in 1953. If the US 6 freeway extension is ever built as planned, the Y-interchange will be demolished.
US 44 was widened to four lanes in Canton in 1984.
Streetscape improvements: Main Street, Winsted
In the late 1990s, Winsted was mulling over streetscape improvements to US 44, which is their Main Street. Their goals included shade trees and various traffic calming devices, including narrowing from four lanes to two; however, the state DOT informed the town that if lanes were removed, "[Winsted] could own the road too" - and pay for its upkeep.
Agreements were eventually reached, however. In 1998 work started on renovating Main Street, and by summer 2003 the work was almost complete. Main Street features a center divider with trees, new sidewalks, and new lampposts along the south side, which is a bank of the Mad River. There are fewer turning lanes, which is slowing traffic in the area.