Commissioned in 1963; most of it was formerly unposted SR 863. This route originally extended only from US 44 to Winchester Center, and the state circa 1960 was planning to turn it over to the town. However, local officials persuaded the state to retain the road, and extend state maintenance from Winchester Center to Route 72 (now Route 272) in Goshen.

In a related matter, the state announced it would not be necessary to take over another local road, Smith Hill Road in the northern section of Winchester, which was once mulled as a possible extension to Route 182.

In 1963, SR 863 became Route 263, yet the road was not improved right away. In 1979, Winsted mayor Kingsley H. Beecher called Route 263 the most neglected highway in the state, and "in deplorable condition." Frost heaves and potholes vexed not only area residents, but firefighters as well, as the bumpy road caused them to drop equipment, boots and hats.

In 1998, the road was resurfaced along a 1.92-mile stretch leading to US 44.

• "Town officials announce state will retain road." Hartford Courant, June 20, 1962.
• "Beecher Calls Rural Rt. 263 Most Neglected in the State." Hartford Courant, Mar. 6, 1979.
• "Resurfacing project begins on route 263." Hartford Courant, Oct. 13. 1998.

• Route 263 Ends (Photos; Doug Kerr at state-ends.com)
• Route 263 - Google Maps