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Route 244 was, at one time, part of the Middle Boston Post Road (later the Boston Turnpike), and was one of the principal roads connecting the cities of Hartford in Connecticut to Boston in Massachusetts and Providence in Rhode Island. It was established as a toll road in 1797 and tolls closed on the road in 1879. On February 1, 1988, the road changed from unsigned State Road 622 to Route 244. Much of the road in Pomfret has been designated as a state scenic route after the town applied for that status to protect its rural character.
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