Gallatin, NY – Douglas Winslow, 68, of Gallatin, NY passed away on May 1, 2019, at Northern Dutchess Hospital in Rhinebeck, NY. Born on August 25, 1950, in Schenectady, NY, Doug was one of three children born to Edwin and Anna Belle (Monesko) Winslow.

To many, he was known as Coach Winslow, a name he cherished and held with great pride. He spent decades doing what he loved most – coaching and working with countless students.

Often, he was the tallest man in the room, but his size was only trumped by his larger-than-life personality and compassionate nature. Anyone lucky enough to meet Doug knows he was a renowned storyteller. He touched many lives with his words of wisdom, jokes, and tall tales. Most will recall the stories of his glory days in the NFL, but his life would not have been complete had he not been able to teach. His booming voice and incredible ability to open his heart to others made him more than just a coach. To many, he was a teacher, mentor, friend, father-figure, and overall inspiration for how we should treat the people around us.

As a graduate of Burnt Hills High School and the University of Massachusetts, Doug accepted an offer from the Buffalo Bills as an Undrafted Free Agent. Although a great opportunity, Doug returned home to be with family and began his career at Roe Jan of the Taconic Hills School District. Here, he acted as a Physical Education Teacher, Varsity Football Coach, Basketball and Track and Field Coach. Doug also taught Little League and Swim Class for the town of Ancram, NY.

In 1993, Doug continued his career at what became his “home away from home”: Webutuck. During his time at Webutuck, he served as an Athletic Director (95-98), JV boys Basketball coach (95-98), Class Advisor (98), and Track and Field Coach (94-09). While there, Doug began serving as the Head Football Coach at Stissing Mountain High School in Pine Plains, NY. This is when he took the initiative to start up (and merge) the Webutuck Football Program with Pine Plains. In 2002, Webutuck finally got their own football program, which filled him with immense pride. He retired from Webutuck in 2012 with a career he held in high esteem. He was recognized many times for his great accomplishments and has countless awards to show for his work over the past three decades.

In his spare time, Doug loved to be outdoors, especially near the water. Fishing, swimming, boating, and just spending time in his “man cave” brought him incredible joy. He was an avid gardener, talented builder, and spent hours on his boat (both in and out of the water).

The only thing Doug loved more than all of this was his family. Doug was a beloved husband, father, brother, uncle, and grandfather (“Pe-Pa”). He is survived by his wife, Lynn Winslow, daughters Catherine Winslow and Audrey Winslow, a son Taylor DeGeorge ( Charlee) and their two sons, Tylor and Jaxon, and a son Eric Winslow (and family). He is also survived by his sister, Carol Sisco and her daughter Lehanne, his brother, Ed Winslow with wife Priscilla and their sons Timothy and Alan, and his niece, Tammy Holdridge-Lasusa and her son Nicholas Lasusa.

We have all been blessed to laugh, cry, love, and learn from Doug. He will be deeply missed but never forgotten.

In celebration of his life, calling hours will be held Friday, May 10 from 4 to 8 pm at the Funeral Home 8063 Route 22, Copake, NY 12516.

Funeral services will be held on Saturday, May 11, 2019 at 11am from St. John’s Lutheran Church in Ancram, NY with Vicar Jackie Jefferson officiating.

In lieu of flowers, memorial contributions may be made to the Douglas Winslow Scholarship Award at Webutuck Central School District 194 Haight Rd. Amenia, NY 12501. You may make checks payable to Webutuck Central School with a memo reading “Douglas Winslow Scholarship Award”.