The Air Line Trail follows the railbed of the former Air Line Railroad which was built to connect Boston and New York City in the shortest distance possible – as if by a “line” drawn through the “air” via the city of New Haven. The section that passes through Lebanon was known as the New Haven, Middletown and Willimantic. It cost $6,000,000 and opened in 1872. The railroad climbed from Middletown to East Hampton, and then went over the Lyman Viaduct, a spectacular 1,100 foot long iron trestle over a deep and wide gorge. The railroad then continued on through North Westchester and Turnerville (Amston) in the southern part of Hebron. The line passed along the boundary of Lebanon and Columbia before dropping steadily down the Ten Mile River valley to Willimantic. The final portion of this section was completed in 1873.

The Air Line is remembered for its fast express trains. There was a succession of these beginning with the New England Limited in 1884. This was succeeded in 1891 by the White Train, popularly known as the Ghost Train. It was made up of gleaming white coaches trimmed with gold. The parlor cars’ interiors were finished in mahogany and furnished with velvet rugs, silk curtains and upholstered plush chairs. The train’s schedule was so well advertised that people came from miles around to wait at stations or crossing to see it go by. The fast express was replaced in 1895 by the Air Line Limited. The decline of the Air Line route came about when passengers and shippers began to prefer the Shore Line Route.

The Air Line railway between Amston and Willimantic played an important role in Lebanon life throughout the nineteenth and twentieth centuries. It not only increased the volume and speed of sending farm products and other freight to market, but also encouraged personal travel. The railroad provided transportation to the cities as well as better mail service for Lebanon residents. Since there were no local high schools at that time, children boarded the train to attend high school in Willimantic. During the summer months, the railroad brought a huge influx of city people to the country for vacations. Many local farm families boarded these summer visitors for the extra income. The railway made possible the start of the resort business still flourishing on Williams Pond.