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Most of Route 57 is a comparatively straight segment in the western section of Weston, following an "eleven o'clock" angle that is common in that part of Fairfield County. (See Eleven O'Clock Road in Weston for an example.) Both Route 58 and Route 59 have sections parallel to Route 57.

"Long lots" were narrow strips of land, up to 10 miles long, surveyed and parceled out in the 18th century. "Upright Highways" followed the north-northwest ("eleven o'clock") angle, and "Cross Highways" (such as Cross Highway in Redding) ran perpendicular (where topography permitted).

CT 57 Turnpikes

The Newtown and Norwalk Turnpike, signposted locally as the Newtown Turnpike, began along today's Route 53 in Norwalk, heading north-northeast toward Newtown. A charter was granted in 1829, and the turnpike operated for about 2 decades. The portion north of the Northfield Turnpike (near the Saugatuck River) became free in 1841, and the remainder was free in 1851.

Route 57 followed part of the Newtown and Norwalk Turnpike for 22 years.

CT 57 History

Route 57 was commissioned in 1932. Its original route was 20.33 miles long, extending from US 1 in Westport to Route 34 (now Route 302) in Newtown. Here are the details, from south to north:

At the time, the Georgetown Road segment of today's Route 57 was part of Route 53.

In 1949, Route 57's official length decreased 0.43 miles, to 19.90 miles; I don't have details on the change.

In 1954, Route 57 was shortened and its northern end was moved. The Newtown Turnpike segment became SR 725. The segment north of Route 58 was removed from the state highway system. Route 57 was redirected along Georgetown Road, replacing Route 53, to end at Redding Road (the redefined Route 53) near US 7. Its length was now 9.51 miles, coincidentally the same as today's.

In 1959, there is mention of a "relocated Route 57" project crossing the Redding - Weston town line, but it's not apparent where the old alignment is.

In 1963, several highways in the area were rearranged. Route 53 was relocated to follow some of the Newtown Turnpike segment of old Route 57. Former Route 53 leading north from Georgetown became part of Route 107.

In Georgetown, Route 57 was extended a short distance west, overlapping with Route 107, to reach US 7. In Westport, Route 57 was moved from the segment of Main Street leading to US 1, and instead followed Canal Street and King's Highway North to end at Route 33.

CT 57 Sources