My uncle called from Baltimore to tell me Irv Naylor had died. He said Ski Roundtop was still packed every weekend, started back in 1964. Ninety one years is a full life.
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Irvin Stanley "Irv" Naylor, a Maryland businessman, ski resort pioneer and champion steeplechase horse owner, <cite index="2-1">died Oct. 20 in Reisterstown, Maryland, at 91</cite>. <cite index="4-3">Born on June 26, 1935 in Stevenson, Md., Naylor was the son of a filling station operator in nearby Pikesville. Irv captained the McDonogh military…
Irvin Stanley "Irv" Naylor, a Maryland businessman, ski resort pioneer and champion steeplechase horse owner, <cite index="2-1">died Oct. 20 in Reisterstown, Maryland, at 91</cite>.
<cite index="4-3">Born on June 26, 1935 in Stevenson, Md., Naylor was the son of a filling station operator in nearby Pikesville. Irv captained the McDonogh military school's cavalry squad during his senior year.</cite> <cite index="4-3">After graduating from Miami University, he launched Lok-Box in 1960, a packaging company that produced wooden boxes. He added Cor-Box, corrugated boxes, in 1968.</cite>
His most lasting legacy, however, grew out of a passion he discovered at Mount Snow, Vermont, in the early 1960s. <cite index="9-5">Irv Naylor originally started Ski Roundtop in 1964. A decade later, Ski Roundtop purchased Ski Liberty. New York's Windham Mountain was purchased in 1981, followed by Whitetail Resort in 1999.</cite> <cite index="1-6">By the mid-'90s, before the Whitetail acquisition, Snow Time did more than $20 million in sales on 650,000 skier visits.</cite> Snow Time sold Ski Windham in 2005 and, in 2018, sold its remaining Pennsylvania resorts to Peak Resorts. <cite index="9-6">In 2004, Irv Naylor was honored with the National Ski Areas Association (NSAA) Lifetime Achievement Award.</cite>
Naylor was equally well known on the steeplechase circuit, where he became <cite index="3-1">the National Steeplechase's all-time leading owner</cite>, with <cite index="2-1">his horses winning three Maryland Hunt Cup titles and three Eclipse Awards</cite>. His own riding career changed forever on <cite index="6-3">April 17, 1999, near the end of the Grand National in Butler, when Naylor's mount, Emerald Action, struck a fence and fell. Naylor hit the turf, head first.</cite> <cite index="6-3">Rushed by medevac helicopter to the University of Maryland Shock Trauma Center, Naylor spent three months in the hospital, regaining the use of his arms but little else.</cite> After months of despair, he returned to the sport as an owner and continued competing on the timber circuit for years afterward.
A philanthropist as well as an entrepreneur, <cite index="2-1">Naylor donated millions for stem cell research, and made a $6 million gift to McDonogh School, his alma mater, that helped fund the Naylor STEM Building.</cite> <cite index="7-3">He also supported McDonogh athletics with a gift to the equestrian program for the construction of the Eagles Nest indoor riding ring, and the Naylor Wrestling Room honors his lifelong love of the sport.</cite>
Naylor's death was announced by the National Steeplechase Association, which described him as <cite index="4-1">a businessman, entrepreneur, and philanthropist who left an indelible mark, collecting accolades and honors from those in the many worlds he traveled in and touched</cite>. He is survived by <cite index="7-4">his wife, Diane; children Scott Naylor, Peter Naylor and Vivian Little; and grandchildren Scott C. 'Chet' Naylor II, Sarah Naylor McPhee and Leah Naylor-Ickes</cite>, and <cite index="7-4">a celebration of his life will be held at a later date</cite>.
Biography adapted from News reports and the sources cited on this page; death reported by SAM Magazine.

My dad skied Roundtop every winter, this one hits different