Over a career spanning more than five decades, Naylor helped establish the viability of skiing in a region where unpredictable winter weather presented constant challenges. Under his leadership, Snow Time grew to include Liberty Mountain Resort, Whitetail Resort, and Windham Mountain in New York. His contributions earned him the National Ski Areas Association’s Lifetime Achievement Award in 2004.
From Blair Mountain to Roundtop
When Naylor arrived in York, Pennsylvania, in 1960, he had never skied. His first experience on skis came during a visit to Mount Snow, Vermont, in the early 1960s. He subsequently began exploring smaller ski areas closer to home, including Blair Mountain, a modest operation near York.
In a March 2008 letter to DCSki, Naylor recalled struggling with Blair Mountain’s rope tow and losing his son’s shoes at the end of a rental day. Those frustrations helped convince him that a larger, better-equipped ski area could succeed in south-central Pennsylvania.
“I remember that and the loss of son’s shoes at the end of a boot rental day as being two of the reasons I started Ski Roundtop — a far bigger mountain with improved technologies and enlightened management,” he wrote.
Naylor eventually identified Roundtop Mountain in York County, where he assembled investors and secured approximately 384 acres of land. Ski Roundtop was incorporated in 1964 with roughly $242,000 in equity and opened for the 1964-1965 winter season with a double chairlift, rope tow, and snowmaking equipment.
Its first winter was difficult. Unseasonably warm, rainy weather during the Christmas holiday threatened the young business, which welcomed approximately 12,500 skiers during its inaugural season. To help finance operations, Naylor sold timber from the property.
“Roundtop’s first year was almost a disaster — it was 60 degrees and rainy/foggy for the entirety of the Christmas week and all of us wondered if we were involved in an ‘impossible dream,’” Naylor recalled.
The resort gradually established itself as a popular destination for skiers from south-central Pennsylvania and the Baltimore-Washington region. Its early history was documented in a 1994 Ski Area Management retrospective, “A Little Giant Turns Thirty,” and in DCSki’s 2018 history of Snow Time.
Building a Regional Ski Business
Roundtop’s success led Naylor to expand his ski operations. In the mid-1970s, Snow Time acquired the financially troubled Charnita ski area near Fairfield, Pennsylvania, renaming it Ski Liberty and investing in improvements. In 1981, the company expanded beyond Pennsylvania with the purchase of Windham Mountain in New York’s Catskills.
Naylor occasionally employed unconventional marketing strategies. During a gasoline shortage around 1980, Snow Time offered to fill the tanks of customers purchasing full-day lift tickets, even purchasing a filling station along Route 15 to support the promotion.
The company’s most consequential Mid-Atlantic acquisition came in 1999, when Snow Time purchased Whitetail Resort near Mercersburg, Pennsylvania. Whitetail had opened during the 1990-1991 winter season with ambitious facilities and quickly became a major competitor to Roundtop and Liberty. Financial difficulties eventually threatened its future, and Snow Time’s acquisition brought three prominent regional ski areas under common ownership.
DCSki covered the acquisition as it unfolded, including concerns about reduced competition and the potential benefits of operating the three mountains together.
Throughout these years, Snow Time invested in snowmaking, lifts, base facilities, and customer amenities. The company also expanded summer recreation and other year-round activities, helping diversify its revenue beyond winter sports.
Naylor participated in national ski industry organizations and received the National Ski Areas Association’s Lifetime Achievement Award in 2004. By the time Snow Time was sold in 2018, its three Pennsylvania resorts were attracting hundreds of thousands of visitors annually and employing approximately 200 year-round full-time workers and more than 3,500 seasonal and part-time employees, according to corporate disclosures filed with the Securities and Exchange Commission.
The End of an Era
In October 2005, Snow Time announced that it would sell Windham Mountain to a group of investors with connections to the Windham community, allowing the company to concentrate its operations in Pennsylvania.
“I have no interest in selling the Pennsylvania resorts, individually or collectively,” Naylor said in the October 24, 2005 announcement. “The sale of Windham Mountain will allow Snow Time management to focus its efforts in one state and one marketplace.”
Thirteen years later, with Naylor retired, Snow Time announced an agreement to sell Roundtop, Liberty, and Whitetail to Peak Resorts. The transaction, valued at approximately $76 million, marked the end of more than five decades of Naylor family ownership.
“I am extremely pleased to pass along the stewardship of Snow Time and our three mountain resorts to Peak Resorts,” Naylor said in the September 2018 announcement. “For more than 50 years, my team and I have grown these three resorts into the magnificent properties they are today, and we are delighted that Peak Resorts will continue to grow their appeal for the next generation and beyond.”
Peak Resorts was subsequently acquired by Vail Resorts in 2019, bringing all three Pennsylvania ski areas into the Epic Pass network. DCSki examined the history of Snow Time in a September 2018 feature, “End of an Era.”
A Passion for Ski History
Naylor also maintained an interest in the history of Mid-Atlantic skiing. In March 2008, he contacted DCSki to share his memories of Blair Mountain and Oregon Ridge, two small ski areas that had closed decades earlier.
His two-page letter included recollections of the people who developed the ski areas, the challenges they faced, and his own experiences during the industry’s formative years. He encouraged DCSki’s efforts to preserve that history, writing, “Congratulations on your research — keep up the good work!”
He closed with a wry observation about how the ski business had changed since his early days:
“It is fun to review this entrepreneurial-started industry which is now controlled by accountants!”
Naylor’s recollections remain preserved in DCSki’s Lost Ski Areas archive.
Beyond the Ski Slopes
Naylor’s accomplishments extended well beyond skiing. Born in Maryland in 1935, he attended McDonogh School, graduating in 1954, and subsequently earned engineering and business degrees from the University of Miami. Before establishing Roundtop, he entered the packaging industry, founding Lok-Box and later establishing additional packaging operations.
He was also a prominent figure in American steeplechase racing. An accomplished amateur rider, he competed for decades before a serious accident during a Maryland race in April 1999 left him paralyzed. He remained deeply involved in the sport as a horse owner, building one of the most successful stables in American steeplechase history. His stable earned seven National Steeplechase Association leading-owner titles and became the association’s all-time leading purse earner in 2024.
Naylor was also a philanthropist, particularly in his support of education and equestrian activities. Having attended McDonogh School on scholarship, he later served on its board of trustees and supported scholarships, athletics, and academic programs. In 2010, Naylor and the Naylor Family Foundation contributed $6 million toward a new science, technology, engineering, and mathematics building at the school.
His accomplishments outside skiing were documented in remembrances published by the National Steeplechase Association and McDonogh School following his death.
A Lasting Legacy
Roundtop, Liberty, and Whitetail remain major destinations for skiers and snowboarders throughout the Mid-Atlantic, continuing to serve the communities Naylor spent much of his career cultivating.
Naylor entered the ski business when regional skiing was still developing and the commercial potential of modern snowmaking was only beginning to be understood. Over the following decades, he helped establish a successful regional ski company capable of attracting hundreds of thousands of visitors despite the region’s unpredictable winters.
His career spanned the transition from independently owned ski hills to large regional resort companies and, eventually, national ownership. More than six decades after he opened Roundtop, the mountains he developed remain an important part of the Mid-Atlantic winter sports landscape.
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