Robert Arnold Osterhout Sr.

Robert A. Osterhout Sr., was a longtime resident of West Stockbridge, Massachusetts, and passed away on June 8, 2026, at the age of 88.

He was born on November 13, 1937, in Pittsfield, Massachusetts. Bob was the first of nine children born to Ellis and Bernice (Vosburg) Osterhout. He was a proud 1955 graduate of Pittsfield High School, who went on to serve his country in the United States Marine Reserves.

Bob was a man of strong work ethic and many talents, but his true professional passion was life on the open road. He spent many years driving tractor-trailers throughout New England, a career he took great pride in. This pride extended to his personal life as well; Bob was known for, keeping his home and vehicles in immaculate condition, a testament to his meticulous nature.

He shared his life with his beloved wife, Helen Magner, with whom he raised their three children, Robert Jr., Tammy and Tracy.

Those who knew Bob will fondly remember his trademark tobacco pipe, his ever-present coveralls when working on a project, and his dedication to keeping everything he touched spotless.

He found great joy in the simple pleasures: fishing with his dear friends Al and John, and the rest of his fishing buddies, taking memorable trips with his friend Steve, trying his luck at the casino, and traveling to spend quality time with his daughter Tracy and her family. His weekends were highlighted by cherished Saturday dinners with Tammy and Gregg, and he always looked forward to tinkering on various projects with his son, Bobby.

Bob’s presence was a steady, grounding force for his family, and he will be deeply missed by all who had the pleasure of knowing him.

Bob is survived by his loving children: Robert Jr. and his fiancée Helene Riiska; Tammy Osterhout and her life partner Gregg Wellenkamp; and Tracy and her husband, Matt Adams. He leaves behind his adored grandchildren: Tori, Amber, Sherry, Lukas, Ashley, and Kyle, as well as his precious great-grandchildren, Lyla, Margot, and Bryson. He is also survived by his siblings: Karen, Ellen, Irene, and Edward.

Bob was predeceased by his wife Helen M. Osterhout on September 3, 2006. The couple was married on June 28, 1958 at St. Patrick’s Church in West Stockbridge, MA. He was also predeceased by his parents, Ellis and Bernice Vosburgh Osterhout, and his siblings, Judy, Beverly, Dorothy, and Lawrence.

Service - The family of Robert A. Osterhout, Sr. will receive friends on Saturday, June 20, 2026 from 9:00 a.m. – 10:00 a.m. at Finnerty & Stevens Funeral Home. The funeral service will be held at 10:00 a.m. at the funeral home with burial to follow at St. Patrick’s Cemetery in West Stockbridge, MA

In lieu of flowers, donations in Bob’s name can be made to the Alzheimer’s Association online at https://Alzheimer's Association / or c/o Finnerty & Stevens Funeral Home, 426 Main Street, Great Barrington, MA 01230. To send remembrances to his family please go to www.finnertyandstevens.com