The alignment of NY 282 between Smithboro and Hoopers Valley originally followed a ferry across the Susquehanna River, dating back to the 18th century, opened by two local entrepreneurs. The ferry was replaced by one opened in 1811 by Caleb Lyons, followed by a wire ferry in 1842 constructed by Colonel William Ransom. On April 18, 1829, the Smithboro and Nichols Bridge Company, with Isaac Boardman, Nehemiah Platt, and John Coryell appointed as commissioners of the new company. The first of the bridges was constructed shortly after the bridge company was improved, but washed away the next spring. In March 1865, the second bridge at the site was constructed, only to be blown apart by a gale in October. After being reconstructed in forty days after the gale incident, the bridge would be demolished when a span of a bridge in Owego village crashed upon the structure. The bridge was rebuilt once again, and survived until 1880, when it was washed away again. This bridge was replaced by a rope ferry to cross the structure. The second of two bridge companies was chartered on June 9, 1899 across the river with a capital stock of $30,000 (1899 USD). This new bridge would be private for 50 years after it would be constructed, with its charter expiring in June 1949. The bridge, constructed by the Groton Bridge Company, was completed in 1899 and contained a toll of 25¢ to cross, covering the return trip.