SAM Magazine—Reisterstown, Md., Nov. 11, 2026—Irvin S. (Irv) Naylor, founder of Snow Time, Inc. (Roundtop, Liberty, and Whitetail Mountains in Pa., and Windham Mountain, N.Y.), died Oct. 20 at age 91. He spent more than five decades developing his resorts, with major investments in snowmaking and infrastructure that allowed his resorts to succeed.
Naylor was also active in the National Ski Areas Association, and received NSAA’s Lifetime Achievement Award in 2004.
Naylor entered the ski business in the 1960s, when success in the Mid-Atlantic region was far from guaranteed—snowmaking was in its infancy. Naylor eventually transitioned to multi-resort ownership and crafted a strong regional presence.
Naylor was introduced to skiing at Mount Snow, Vt., in the early 1960s. He began looking for options closer to his home in York, Pa., and was not satisfied with what he found. That motivated him to launch Ski Roundtop in 1964. He invested in snowmaking, lifts, and other infrastructure, and the resort attracted guests from the Washington-Baltimore area and south-central Pennsylvania.
To expand its reach, Snow Time purchased Charnita ski area in 1976 and renamed it Ski Liberty, and Windham in 1981. Snow Time added Whitetail, which had launched in 1990 and competed with both Roundtop and Liberty, in 1999.
By the mid-’90s, before the Whitetail acquisition, Snow Time did more than $20 million in sales on 650,000 skier visits. More significantly, the company showed a pre-tax profit of 20 percent, as SAM reported at the time.
Snow Time eventually sold Windham to local investors in 2005, and focused on its three Pennsylvania ski areas until 2018, when it sold them to Peak Resorts (which subsequently sold its 17 ski areas to Vail Resorts in 2019).
Naylor had established his business chops before entering the ski biz. He earned engineering and business degrees from the University of Miami and founded Lok-Box, eventually adding other packaging businesses as well.
He was also active in American steeplechase racing. He competed for decades as an amateur; a serious accident during a race in 1999 left him paralyzed.
Among his philanthropic interests, Naylor contributed generously to educational and equestrian groups. In 2010, Naylor and the Naylor Family Foundation contributed $6 million toward a new science, technology, engineering, and mathematics building at McDonogh School in Maryland, where he gained his elementary and high school education.
As described in the article “A Little Giant Turns Thirty” (SAM, November 1994), Naylor was a “forceful, energetic boss” with a unique management style, distilled by his then executive committee into three basic rules:
1) *Surprises*—Irv hates them, especially if something’s going wrong. When in doubt, let Irv know what’s happening and what you’re doing about it. 2) *Mistakes*—Everyone makes them, but learn from them. With Irv, best not make the same mistake twice! Naylor aphorism: *“A smart man learns a lesson from his mistakes; a really smart man learns lessons from the mistakes of others.”* 3) *Facts*—Master them, then assemble them. If you need money for a project, for instance, assemble all the relevant facts and make a good, logical case. Without holes. Chances are you’ll get the money. The converse is equally true: better not try to make your case if you’re at all unprepared. He’s always so well prepared himself you’ll never be able to fake it.
