William F. Dempsey of Castle Street died peacefully at home July 22, 2018, at the age of 100.
Mr. Dempsey (Bill), an automobile dealer in Great Barrington for many years, was born January 24, 1918, in Bridgeport, Connecticut to Matthew J. Dempsey Sr. and Beatrice Clarkson Dempsey. He moved with his family in 1921 to South Egremont where he attended school, and graduated in 1935 from the former Searles High School in Great Barrington. He also attended General Motors School of Accounting in Springfield in 1947.
His father established the first Dempsey’s Garage in 1921 at the site of an old livery/buggy business in South Egremont and, in 1928, was granted the Pontiac dealership and later the Buick and Oldsmobile franchise for southern Berkshire. The family moved the business to Great Barrington in 1937, operating on Railroad Street until 1947 when Mr. Dempsey and his brother, Matthew J. Dempsey Jr., took over the business and moved it to 42 Bridge St.
Mr. Dempsey went to work with his father while still in high school and stayed in the business for over 50 years. He retired in 1983. He and his wife loved to travel and, for decades, traveled across the country in a motor home, visiting 48 of the 50 states. He enjoyed driving, tinkering and puttering, and could fix most anything. He loved people and would often help friends and neighbors with any car or RV problems.
Mr. Dempsey was a member of the First Congregational Church in Great Barrington, a longtime member and past president of Great Barrington Rotary, a member of the Veterans of Foreign Wars, a member of the American Legion, a former board member of the Great Barrington Savings Bank, and a 70-year member of the Great Barrington Cincinnatus Lodge. He served in the United States Navy from 1941–45, serving 29 months during that time on the island Espiritu Santo in the New Hebrides. He was a crew member of the “200” stock car team at Lebanon Valley Speedway for many years and was also a longtime member of the Wyantenuck Country Club.
He leaves his beloved wife of 68 years, the former Lucile Rae, whom he married November 17, 1949; his son-in-law William Gutowski of Ames, Iowa; his granddaughter Sarah Gutowski of Iowa City, Iowa; a brother-in-law and several sisters-in-law in North Carolina; as well as many nieces, nephews, great nieces, great nephews and several cousins. He was predeceased by his daughter Margaret (Peggy) Gutowski, his son John Dempsey, his sister Alice Bowen and his brother Matthew J. Dempsey Jr.
Bill will be remembered for his integrity, generosity, kindness, wry wit and gentle spirit, and will be missed by all who loved him.
A funeral service to celebrate the life of William F. Dempsey will be held Monday, July 30, 2018, at 11 a.m. at the First Congregational Church, Main Street, Great Barrington, conducted by Rev. Randall Willburn. Burial with military honors will follow at Elmwood Cemetery. There will be no calling hours. Memorial contributions in Bill’s memory may be made to the First Congregational Church, Great Barrington, or to Fairview Hospital, Great Barrington, in care of the FINNERTY & STEVENS FUNERAL HOME, 426 Main St., Great Barrington, MA 01230. To send remembrances to the family, visit http://www.finnertyandstevens.com.
