The ongoing remaking of the Holiday Mountain Ski Area outside Monticello under the visionary guidance of new owner Mike Taylor and his dedicated staff has thrust skiing back into the local spotlight like it hasn’t been for many years.

Although it was not the first ski hill to operate in Sullivan County, it certainly revolutionized skiing here when it opened for good on December 24, 1957, billing itself as the closest ski area of its kind to New York City. At the time, the hill featured two rope tows, and a 900-foot Poma-lift shipped in from France and installed just in time for the opening. This state-of-the-art lift could handle 900 skiers an hour. The ski area’s trails and slopes all had holiday-related names, including “Easter Parade,” “Birthday Schuss” and “Christmas Bowl.” Refurbished development also offered skiers a new ski lodge and chalet, a restaurant, and a ski shop where 100 pairs of skis and 50 pairs of Swiss ski boots were available for rent. “It will be no layout to captivate the imagination of experts accustomed to tearing down Stowe’s Nosedive or Mount Greylock’s Thunderbolt, but it will more than suffice for the run-of-the-mill sports lover who wants to test his legs as well as enjoy the sport with a minimum risk of injury,” predicted The New York Times in its December 8, 1957 edition, a couple of weeks before the grand opening.

Of course, by continuing to evolve, Holiday Mountain became much more than that. And now, with the new leadership at the helm, and opening day having arrived, the sky seems the limit. While it has long been known that even in its earliest incarnation in 1949, when it offered skiers three electric tows, open slopes, expert trails, a Swiss Ski School with instructors, a warming hut with refreshments, and a ski shop, Holiday was not the first commercial ski operation in the county—both Walnut Mountain in Liberty and Christmas Hills in Livingston Manor predated it—it has only recently come to light that it was not even the first ski operation in Monticello. That distinction belongs to Wintergreen Hill, which while not a commercial venture per se, hosted skiers as far back as the early 1920s.

The use of Wintergreen Hill, located about a quarter of a mile from the village on what is now called Old Liberty Road in the vicinity of where the road now passes over the Route 17 Quickway, apparently dates to 1923—more than ten years before the Walnut Mountain venture in Liberty - at least according to an article in the February 9 edition of the Republican Watchman newspaper that year. The article summarized the most recent regular meeting of the Monticello Athletic Club, held earlier in the week at Fireman’s Hall on Broadway in the village with “a large number” of the club’s 121 members in attendance. “The subject of skiing as a winter sport was also fully discussed,” the article reported. “The Club’s purpose is to make Monticello as great a winter resort as Saranac Lake. Various places for the sport were discussed, the most favorable being Wintergreen Hill on Liberty Street.”

The Club apparently appointed a committee consisting of Leslie Hicks, Howard Thompson Isaac Silberman, John Ennis, and George Hembt to investigate the use of the hill for skiing and report back. The article continued:

“Wintergreen Hill is probably the most suitable place for a skiing course. It is in close proximity to the village and possesses great possibilities for both skiing and tobogganing. It was decided that all members of the association meet on Wintergreen Hill at 3 o’clock on Sunday afternoon and look over the proposed courses. At that time, pictures will be taken to be used for advertising Monticello for winter sports. All residents and visitors in the village are invited to be present on that afternoon. Any persons having skis should bring them. Those pictures will be used by the O&W Railway in their advertising campaign.”

Wintergreen Hill was once owned in its entirety by a man named George F. George. Around 1909, after years of trying to sell the entire piece, he divided the 64-acre property into lots and auctioned them off. Prominent Monticello businessman John J. Burns, who owned a clothing store on Broadway, purchased about 26 acres of the land in 1911, and as late as 1922, having sold his Broadway building but not his clothing business within it, announced he was contemplating constructing a hotel on the Wintergreen Hill property. He did not.

Research into skiing on Wintergreen Hill is continuing, and it is hoped that perhaps some of the photos taken of the Monticello Athletic Club members there in February of 1923 or the advertising done by the O&W Railway of Monticello as a winter sports destination will surface. Stay tuned for more information.

In the meantime, the rebirth of Holiday Mountain should be celebrated, as it once again, just as it did in 1957, revolutionizes skiing here.

John Conway is the Sullivan County Historian. Email him at jconway52@hotmail.com.