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It's probably coincidence, but Route 244's number hints at its optional role as a bypass to US 44 in Eastford and Pomfret. A 3.1-mile section from Route 97 to Chase Pond Road is a state scenic road.
Also, 244 is Connecticut's newest signed route number: before its designation in 1988, it had never been used for any route before. Among other "new" routes: I-691 appeared in 1987; I-291 was preceded by State Route 291; and Route 130's number first appeared in the 1920s.
Route 244 is part of the 19th-century Boston Turnpike, a toll road leading from Hartford toward Boston by way of Manchester, Coventry, Ashford, Pomfret and Thompson. The turnpike was established in 1797 and was disbanded in 1879. A former tollhouse is still visible from Route 244.
Today's Route 244 was originally locally maintained.
In 1953, politicians in Eastford and Pomfret submitted a state bill to add Boston Turnpike and Shaw Hill Road (now called Brayman Hollow Road), from Route 198 to Route 97, to the state highway system.
In 1962, the roads were added, on the recommendation of the state Committee to Reclassify All Public Roads, as unsignposted SR 622.
On Feb. 1, 1988, SR 622 was promoted to signed Route 244.
The start of Route 244 westbound, as seen from Route 97. Photo taken Sept. 2002 by Kurumi.
In late 2002, officials in Eastford and Pomfret applied to the state for scenic road status for all of Route 244. This would help protect the road from widening or other changes that would mar its scenic character.
On Feb. 21, 2003, the state designated a portion of Route 244 as scenic: 3.1 miles, from Route 97 to Chase Pond Road.
"I took a shortcut between Willimantic and Putnam when I selected State Route 244 in lieu of U.S. Route 44. All I got for my trouble was a very steep (about 15%) hill coming up from the bridge over a small river. I muttered about that one a lot - thankfully it wasn't a very long hill. I think I saved a mile or two, but I don't think I saved any time."