Before the High Line became the park in the sky, before it was abandoned, before trains ran goods along its once thirteen-mile length, before its massive, trunk-like beams sprouted from the cobblestones to suspend its metal canopy above the streets below, the West Side of New York churned with reckless energy. Freight trains ran at grade up and down the middle of 10th Avenue, tracks inserted between cobbles, to ferry goods to and from the factories of the Meatpacking District. This interplay of heavy machinery and humanity proved a dangerous mix; the stretch of road became known as “Death Avenue.”
On December 4, 1850, City Council passed a law that created not only a safer 10th Avenue, but also one of the most storied figures in the history of New York: the West Side Cowboys. These men, as the law dictated, rode on horseback before oncoming trains to warn passers-by of their approach. Waving a red flag by day and a red lantern by night, the West Side Cowboys – also known as 10th Avenue Cowboys – protected pedestrians for over 90 years, until their final ride in 1941 . At its height, the corps of Cowboys comprised twelve riders and twice as many horses to provide perpetual protection. By the end, though, there was just a single rider and his steed left.
The Cowboys themselves were an interesting breed. Employers preferred experienced riders from the country  over city natives as they could better handle their horses in the high-stress environment of New York, which could prove too much for a novice equestrian with a skittish mount. The riders were tried-and-true projections of the Old West dream in New York – real country cowboys leading herds of rail cars to pasture. Alien in image and origin to the urban environ, the West Side Cowboys quickly claimed a place in the collective conscious of New York. They captured the attention of countless New Yorkers. Descriptions of them featured in a 1934 newsletter called the London Tattler, Hell’s Kitchen native and author Mario Puzo included them in his 1965 novel The Fortunate Pilgrim, and they were still fondly recalled by elderly New Yorkers in recent years, often to the disbelief of those listening . There’s even a children’s book  about a boy from out West who moves to the city and becomes one of the iconic Cowboys.
Despite their constant vigilance, the efforts of the Cowboys were not enough. Popular opinion still fell heavily against street-level freight trains and manifested as a group named the League to End Death Avenue. In 1929, the West Side Improvement Project began with the ultimate goal of moving rail traffic above the street. In 1934 the High Line opened, connecting warehouses and factories above the street and leaving foot and motor traffic in peace below. The old Death Avenue rails were all but abandoned, much like the High Line decades later. With street level rail traffic decreasing, the Cowboys faded from the unlikely Wild West of the Meatpacking District . The final ride of the West Side Cowboy occurred on the morning of March 29, 1941, as 21-year-old George Hayde  and his horse, Cyclone, heralded the passage of 14 freight cars loaded with oranges.
Although 72 years have passed since the West Side Cowboy's final ride, their image and story still capture the interest and curiosity of New Yorkers. How odd it must have been to first lay eyes on a chaps-wearing, flag-waving cowboy galloping down 10th Avenue ahead of a steaming train. With a real cowboy hat, no less! Both the West Side Cowboy and the functional, freight-carrying High Line have become entries in the long book of New York City history. During their respective heydays the two served the same purpose: to protect pedestrians from the dangers of heavy rail. Now the memory of the cowboys and the current incarnation of the High Line reunite once more, over the gulf of more than 160 years, for a more pleasant cause: to enthrall the hearts, minds, and imaginations of New Yorkers.
See a rare video of a West Side Cowboy in action on Annik LaFarge's excellent blog, Livin’ The High Line .