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 locally maintained until 1963, when it was added to the state highway system, on the recommendation of the state Committee to Reclassify All Public Roads. Its number was unsignposted SR 622.
On Feb. 1, 1988, SR 622 was promoted to signed Route 244.
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."