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The valley is located in a glacial trough (Folly Gap) north of Folly Mountain and comprises the lowest elevation pass through the Cobequids. It was named after the colonial governor John Wentworth (1792-1808).
The valley is the shortest route between Halifax and the Isthmus of Chignecto border with New Brunswick. In 1872 the Intercolonial Railway built its mainline between Halifax and Rivière-du-Loup through the valley, rising along its western walls to gain altitude to reach the summit at Folly Lake.
Highways followed the railway during the 20th century and Trunk 4 was built through the valley and over Folly Mountain. During the early 1960s this road was redesignated Highway 104, the Trans-Canada Highway. In 1996 a toll highway was built over the much higher altitude Cobequid Pass to the west and the valley's roads reverted to a secondary route.
The valley hosts the communities of Wentworth, Wentworth Centre, Wentworth Station, and West Wentworth. In the nineteenth century there were watermills on the Folly and Wallace Rivers and copper was mined from the bedrock. A copper smelter operated for a short time at West Wentworth.
- "Many Watermills and Two Copper Mines Once Operated At Wentworth", The Oxford Journal, March 23, 1972
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