Long before the Delaware River bridges the river was used by timbermen's log rafts headed for Philadelphia saw mills and later, mills of Easton and Phillipsburg. Some of these timbermen crews took days to make the trip, stopping at towns with taverns overnight for food, entertainment and such. Some, such as the champion Callicon timberman, Elias Mitchell , also known as "The Deacon", could make the trip in twelve hours by overnight and dangerous traveling.
In 1886 the "Callicoon Echo" newspaper reported the first meeting of bridge supporters being held at the local Everard House Tavern, saying the Cochecton-Demascus bridge, ten miles down stream, was too far away to serve their growing community. Interest and support continued but it was ten more years before a bridge was built. The Callicoon Bridge Company was formed in 1898 , headed by Charles T. Curtis, $25 shares were sold and property was purchased and a contractor, Horsehead Bridge Company, began the construction, a suspension structure, at a cost of $23,200, which opened on 1899.
Horseheads Bridge Company was owned by brothers, James, Will and E. Perkins of Horseheads, New York, who built other Delaware River bridges and were well known bridge builders. .
A local man, Jacob Knight, a harness maker by trade, was named toll collector sand lived in the toll collectors house at the bridge and by 1906 was Director of the bridge company.
There was a party on opening day, January 4, and no toll was charged that day but thereafter the bridge was open and operated for business and profit, first year earning $1254.00. The Erie Railroad ran on the Callicoon side and the bridge gave good service to the Callicoon Station.
The bridge survived several floods and in 1904 needed to be raised at the cost of $2849 paid to Horseheads Bridge Company. .
On February 8, 1923 the Bi-State Bridge Corporation, Pennsylvania and New York, bought the property for $35,0002 from the privater owners and Callicoon Bridge Company was no more. Tolls were discontinued. Old age, not the floods,caused the downfall of the old bridge, heavy truck traffic , etc., It was decided to replace it in 1963, located slightly downriver by The Binghamton Bridge and Foundation Company which was much larger and sturdier, still toll free, is leading and active life.
SOURCE; Frank T. Dale's Bridges over the Delaware river.