Although the number of Sullivan County hotels open during the winter months increased significantly beginning in the 1940s, there were attempts to market the county as a winter resort long before that.

It is known, for example that as early as 1926, Shindler's Prairie House in Hurleyville was open—tragically, as it turned out—for Washington's Birthday weekend, entertaining about forty guests. A fire that started in one of the hotel's chimneys that weekend killed twelve guests and staff at Shindler's, and caused many smaller resorts to reassess the wisdom of opening in winter.

Nonetheless, by the winter of 1928-29, a few hotels were doing a brisk business during winter holidays.

“Sullivan County, long known as a summer resort, is fast assuming an importance as a winter resort also,” the Liberty Register newspaper reported in its January 3, 1929 edition. “For the past several years there has been a large annual increase in the number of New York City guests who spend several weekends in Sullivan County during the winter months, and this increase has reached its greatest point this year.”

The Register noted that the weather was a key factor in determining the success of the winter season at Sullivan County hotels, where snow was mandatory for snowshoeing, sleighing and tobogganing, but snow storms that created hazardous travel were a detriment in attracting guests. The previous holiday weekend, it reported, had brought clear roads, but with plenty of snow already in place.

“The Grossinger hotel, which has been among the fore in sensing new trends in its business, reports a holiday season without equal in the past. The number of guests entertained at this hotel for the holidays exceeded even some of the most prosperous weekends of the summer.”

According to the Register, Grossinger's had registered some 850 guests for the holidays, 380 of whom had to be housed elsewhere for lack of heated accommodations. Grossinger's reported it had to turn away 600 prospective guests.

Youngs Gap, “the luxurious new hotel on the heights north of Liberty,” was also “crowded to capacity with a joyous crowd of young people,” and other hotels in the vicinity also had “good sized crowds.”

Following Washington's Birthday weekend in 1941, Grossinger's “the largest of the winter sports resorts” reported that it had entertained “the largest number of guests in its history, winter or summer.”

“Not only was the hotel itself filled, but overflow crowds were housed at affiliated places in Liberty village,” the Register reported on February 27, 1941. “Guests at all of the resorts expressed themselves as well-pleased with the Sullivan brand of winter sports. At Grossinger's, a complete list was available-- ski races, skating, tobogganing, and indoors entertainment and dancing.”

The Register reported that Monticello resorts were also “filled to capacity and overflow accommodations were also filled.”

By 1964, as many as 50 of the county's hotels were open for winter business, although not necessarily all throughout the winter, as some chose to operate only on holiday weekends.

Wolf Olkin, the owner of the Youngs Gap Hotel as well as a director of the Sullivan County Hotel Association, told the Register that he was “enthusiastic and optimistic” about the continued growth of the winter hotel business.

“At his hotel, which has a capacity of 450, several weekends and the Christmas-New Year's holidays were sell outs,” the Register reported in its January 30, 1964 edition. “‘More skiers are coming to the county than ever,' said Mr. Olkin, who explained that more colleges are having inter-session dates which brings college groups of from 100 to 150 to the hotels for skiing. These groups are a big boost to winter business. Ice rinks, indoor pools, and ski centers attract winter resort guests, stated Mr. Olkin.”

Olkin told the Register that the Youngs Gap, which had constructed an indoor pool and indoor skating rink just a few years before, had no construction plans heading into that summer, but was considering further expansion the following year. Sadly, that was not to be the case.

Ironically, immediately adjacent to the Register's article about the increase in winter resort business, were printed two legal notices of foreclosures against Sullivan County hotels, foreshadowing a trend of failures that would become all too common over the next few years. By 1967, Even the Youngs Gap had closed its doors.

John Conway is the Sullivan County Historian. Email him at jconway52@hotmail.com. On Thursday, January 28 at 6 p.m. he will join Marvin Rappaport and Steve White via ZOOM to present a program for the Crawford Public Library in Monticello entitled “The Borscht Belt in Winter.” Call the library for registration information.