Herbert George Tenney, 95, of South Egremont, died January 16, 2026, in Great Barrington of cancer. He was born in Glendale, Mass., on February 26, 1930, the youngest of eight children to Hugh L. Tenney and Effie L. (Stowell) Tenney, and lived his whole life in southern Berkshire County. He was named after President Hoover and his uncle George Stowell.
Herb attended school in Glendale and, at the age of 14, began working after school, weekends, and summers at Boulder Farm on Ice Glen Road in Stockbridge. His brothers, Ralph, Raymond, Charles, and Robert, served during World War II, and he wanted to serve too. So, in 1949, he joined the U.S. Army with his friend Francis McCormick and served one year at Fort Hood in Texas. He and Francis then served four years in the U.S. Army Reserves at Camp Drum in New York.
Following his honorable discharge, Herb worked for Ernie Hall’s taxi service in Stockbridge, driving mostly wealthy summer residents and Norman Rockwell. For Rockwell, he delivered paintings to New York City, took him to business meetings, drove models to and from Rockwell’s studio, and assisted with personal matters such as driving him to Haverford College in the middle of the night in a snow storm when his son Peter was seriously injured in a fencing accident. One model that Herb brought to Stockbridge was Gloucester, Mass., lobsterman Walter E. Merchant, who appeared in Rockwell’s 1955 painting “A Fair Catch.” Herb also modeled for Rockwell himself and appeared in several works, including advertising for Texas Commerce Bank in 1955 (“Seeing Your Name in Lights”), advertising for Shell Oil Company in 1957 (“You Can Build a Fine Future with Shell”), and artwork commissioned by the American Petroleum Institute in 1959 (“Oil’s First Century”) for the centennial of oil’s discovery in the U.S.
From 1954 to 1957, he helped complete the last 22 miles of the Massachusetts Turnpike from Becket to the New York state line directing traffic, hauling gravel, and installing stock fencing and guardrails. Herb then chauffeured for Mrs. Bruce W. Sanborn of St. Paul, Minn., and her son Carl Weyerhauser until 1969. She was a summer resident of Lenox and a patron of Tanglewood and other projects such as moving the Shaker Meeting House from Shirley, Mass., to the Hancock Shaker Village in 1962. Herb then began a 23-year career at the Austin Riggs Center in Stockbridge, working on grounds maintenance with his friend George Schneyer. Following his retirement from Riggs in 1992, he continued working for another 14 years as caretaker for an estate on Prospect Hill Road in Stockbridge.
Herb loved everything in nature and being outdoors. He hunted with family and friends from the age of 16 until he was 85—mostly for rabbits, raccoons, turkeys, and deer in Vermont and Massachusetts. He also went on three moose hunting trips to Newfoundland and one caribou hunting trip to Northern Quebec. No game ever taken by Herb was wasted. He also enjoyed fishing, deep-sea fishing, snowmobiling, and golfing. He played golf for 70 years until he was 91 and had two career holes-in-ones. Herb also loved singing, playing, and listening to country music. He had a beautiful tenor voice and was a self-taught musician from a young age who played guitar, mandolin, fiddle, banjo, harmonica, and piano—all by ear. With other area musicians, he helped entertain guests at many Berkshire County square dances, kitchen dances, block dances, and house parties, including at the Grange Hall in Sheffield and at Ashintully (the Tytus mansion) in Tyringham. He and his brother Charles and their cousin Gerry Malone also led sing-alongs to the absolute delight of their large family at birthdays, anniversaries, and annual reunions for over 60 years.
Herb is survived by his loving wife Elaine Tenney, whom he married on June 18, 1983, and who was devotedly by his side until the end. He is also survived by sons James Tenney and Scott Tenney; stepchildren Stephen Collins (Ginger), Deborah Kiriakedes Kuboyama (Shin), Michael Kiriakedes (Barbara), and Theresa Kiriakedes Marsh (Robert); grandchildren Andrew Kiriakedes (Aly), Karina Kiriakedes Baldelli (Brad), Charles Tenney, Katherine Tenney, Mikalah Tenney (Michael Burchette), Garrett Marsh, Deana Marsh, and Michael Marsh (Katie); and great-grandchildren Kaylyn Tenney, Beau Baldelli, Leo Baldelli, and Michael Kiriakedes.
A graveside service with military honors will be held at the Stockbridge Cemetery in the spring. In lieu of flowers, memorial donations in Herb’s name may be made to the American Cancer Society (Relay for Life of Berkshire County, Gardino’s Gang) in care of the Birches-Roy Funeral Home, 33 South Street, Great Barrington, MA 01230.
