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The Connecticut Company drb04
Derby Division
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The car is northbound on the Stratford - Derby line, headed for Shelton. There is DERBY is on the rear roll sign, and the river is on the cars right, making it the Housatonic River. The car is crossing the High Bridge south of Shelton, and was still on Bridgeport Division trackage (Derby Division started closer to Shelton). Note the car has no built-in headlight and a basket fender, which makes it a CR&L car from either Bridgeport or Derby divisions. The roll sign style is Conn Company, however, so the photo is likely taken between 1907 and 1915.
Joe Testagrose photo