The Air Line State Park Trail gets its name from the term once used to describe some railroads that conveyed the straightest practical means of connecting to points, or an “air line.” Nearly all such projects failed, since the idea of building a railroad via a tangent line proved far too expensive due to their numerous large fills, cuts, bridges, and tunnels needed to scale the rugged landscape in the east. This particular trail uses a right-of-way first constructed during the 1860s and meant to connect New York with Boston via an inside gateway to compete against the New York, New Haven & Hartford’s (the New Haven) route, which hugged the Long Island Sound coastline. Ultimately, the system that became known as the New England Railroad was eventually acquired by the New Haven. As the years passed, the secondary route became superfluous, and much of it was abandoned during the 1960s.

Both the north and south segments of the Air Line Park Trail use the same rail corridor, albeit each was originally built by a different railroad. The earliest component to actually have rails struck out west from Boston. The history of this route is a tangled mess of failed and bankrupt systems, the earliest of which was chartered as the Norfolk County Railroad of 1847. It eventually became known as the Boston, Hartford & Erie Railroad (BH&E) that, by the 1860s, connected Boston with Mechanicsville, Connecticut. In August 1872, the route was opened to Willimantic, where it linked with the New Haven, Middletown, & Willimantic (NHM&W). This particular railroad had been chartered in 1867 and was the latest project to see an “air line” constructed between Boston and New York (the original New York & Boston Railroad Company of 1846 had little success).

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Not surprisingly, the air line concept was later dropped because of cost overruns and expenses far exceeding available capital. Instead, the NHM&W decided to complete the route to Boston by connecting with the BH&E, opening a line from New Haven to Middletown by 1870 and then to Willimantic by 1873. That same year, BH&E acquired NHM&W, which entered bankruptcy once more and emerged as the New York & New England Railroad. The NY&NE became a staunch competitor to the New York, New Haven & Hartford, which had been formed around the same time. Both railroads served similar markets, and the NY&NE would later have access to the Poughkeepsie Bridge, which opened in 1888 and served as a northern freight artery into New England, bypassing busy New York City. Following the Panic of 1893, the NY&NE fell into bankruptcy, becoming the New England Railroad in 1895. The New Haven was finally able to gain control of its rival by leasing the property in 1898; it formally merged into the NYNH&H in 1908.

The New Haven may have been only a regional railroad in size, but in many ways it was New England’s most important, providing a direct high-speed rail corridor between Boston and New York, part of which was electrified south of New Haven. Commuters throughout Connecticut, Rhode Island, and southern Massachusetts depended on the New Haven to get to and from work every day. The railroad was also an important freight artery during New England’s industrialized era, with branch lines sprawled throughout each state and connections to every other notable railroad in the region, including the Boston & Maine, Central Vermont, and New York Central/Boston & Albany. There was also the gateway route through Poughkeepsie via Maybrook, New York, that provided additional interchanges with the Erie Railroad, Lehigh & New England, Lehigh & Hudson River, New York Central, and New York, Ontario & Western.

The New Haven’s heavy reliance on passenger traffic, which was never terribly profitable especially in an era before subsidization, meant the railroad was much more susceptible to financial trouble when the economy was in limbo. This was no truer than during the Great Depression, which forced the New Haven into receivership in 1935. It was able to regain its footing with the start of World War II and the flood of passenger and freight traffic that followed, which allowed the railroad to emerge from bankruptcy in 1947. Unfortunately, it was plagued with poor management during the 1950s, a decade during which it failed to post a profit except for in 1956. The former New England Railroad lines, which was referred to as the “Air Line Route,” primarily served in a secondary role during the New Haven days, in part because of its numerous steep grades and sharp curves.

By the World War II era, the Air Line was seeing little through traffic from Boston to New York except for local freight customers. In 1955, severe flooding washed away a bridge over the Quinebaug River, northwest of Putnam, Connecticut. With the railroad struggling and the corridor hosting few trains, it elected to abandon the line between Pomfret and Putnam. During 1961, the New Haven entered its final bankruptcy and continued shedding more of the Air Line in an effort to improve its financial situation. The North Windham to Pomfret segment was the next to go in 1962, and an even larger section, Portland (just northwest of Middletown) to Willimantic, was abandoned in 1964. A few years later in 1968, the New Haven was included in the Penn Central merger, the poorly conceived union of the New York Central and Pennsylvania.

By 1970, except for a few short segments, the entire Air Line Route from Portland to Franklin, Massachusetts, had been abandoned. The rest of the line to Boston and New Haven survived and is still in use today; the former is operated by Massachusetts Bay Transportation Authority (MBTA) for commuter service, while the latter is owned by the Providence & Worcester Railroad for freight traffic.

Railroad attractions near the trail include the Connecticut Eastern Railroad Museum in Willimantic; the Connecticut Trolley Museum in East Windsor; the Danbury Railway Museum in Danbury; the Essex Stream Train in Essex; the Naugatuck Railroad in Thomaston; the Shore Line Trolley Museum in East Haven; and the SoNo Switch Tower Museum (a former New Haven switch tower) in South Norwalk.