Henry Raymond Hilliard Jr.

Henry Raymond Hilliard Jr.
1921 - 2014
Henry Raymond Hilliard Jr., 92, of Cumberland Foreside, died peacefully surrounded by his family on Feb. 1, 2014. He was the son of Elizabeth Levering and Henry Raymond Hilliard of Pittsburgh, Pa. At age 12 while attending Shady Side Academy in Pittsburgh he lost his father to a sudden illness. The following year he entered St. Paul's School in Concord, N.H. Later in life Henry would often remark that his years at SPS gave him the guidance and mentorship he sought, as the oldest son, to fill his father's shoes; he consequently fostered a lifelong relationship with the school and many of his teachers and classmates.
After graduation from St. Paul's in 1939, Henry entered Princeton University enrolling in an accelerated program to graduate early in 1943, and join the war effort. He served in the 649th Company of U.S. Army of Engineers, where he was responsible for analysis of aerial photographs and the production of maps to guide the troops in Europe.
After the war Henry returned to the United States and traveled to New York City. There, he landed a job at Time Magazine where he met his future wife Anne, a researcher in the editorial department. They married in 1946 and soon after moved to his hometown of Pittsburgh, Pa. In 1953, after several years as a trust officer at the Mellon Bank in Pittsburgh, Henry struck out with his young wife and growing family for the coast of Maine following his love for the sea and the mountains. There, he entered into a partnership with Harry Parker at the South Freeport Yacht Basin, and worked for the First National Bank of Commerce in Portland. Later, Henry bought The Tucker Printing Company in Portland, and served as the President of The Portland Museum of Art. Henry and Anne winterized a lovely summer home on the grounds of the old hotel, "The Gem of The Bay" on Prince's Point in Yarmouth; there they moored their first boat, Windward, the name he gave all his boats. Henry began to take his family on frequent ski trips to Sugarloaf, back in the days of Amos Winter when the only lift was a rope tow.
In 1962 the family moved to Concord, Mass., and Henry took the position of Assistant to President Asa Knowles of Northeastern University, and later Director of Personnel. Upon the retirement of President Knowles, Henry took the position of Director of Human Resources with Dynamics Research Corporation (now Engility) in Wilmington, Mass. He joined the Cambridge Boat Club to take up again his love of rowing which he'd begun at St. Paul's School and continued at Princeton. Henry raced for many years in the Head of the Charles Regatta, in the Master Division.
In 1986 Henry retired from Dynamics Research Corporation. He and Anne returned to Maine and settled again on Casco Bay near old friends where they built a lovely modern home on Cumberland Foreside within rowing distance of their former home on Prince's Point. Henry volunteered for ITN (Independent Transportation Network) and for the Ocean View Retirement Community, where he made many new friendships with residents while transporting them to appointments. He also mentored middle school students in personal finance, taught ESL to immigrants in Portland, and served on the Vestry at St. Mary's Church in Falmouth.
Henry re-joined the Portland Yacht Club, was honored to be invited to join the Fraternity Club, a small men's group, and enjoyed lunching with the R.O.M.E.O.'s ("Retired Old Men Eating Out"). He took great pleasure in sailing his Pacific Seacraft with family and friends, and completing a long sought goal to cruise from the St. Lawrence Seaway down the eastern seaboard and through the Intracoastal Waterway, across the Chesapeake and on to the Carolinas.
Henry leaves his wife of 67 years, the former Anne Fitzhugh Rose of New Haven, Conn.; his children, Melissa R. Hilliard of Old Orchard Beach, Larkin L. Hilliard of Pacific Grove, Calif., Henry R. Hilliard III of Brooksville; his grandson, Willem H.O. Hilliard of Blue Hill; Christina F. and her husband Mark Lamkin of Framingham, Mass.; and many nieces and nephews. Henry was predeceased by his brothers, George Webb Hilliard in 2011, and Richard Levering Hilliard in 2012.
Henry was profoundly grateful for the generous and compassionate services of many committed individuals at the Visiting Nurses Association, Hospice of Southern Maine, Gosnell Memorial Hospice House in Scarborough, the Iris Foundation in Portland, and Carol Barber of the Southern Maine Agency on Living.
A memorial service will be announced at a later date.
In lieu of flowers, donations may be given in his name to Merrill Memorial Library of Yarmouth and Gosnell Memorial Hospice House in Scarborough.

Published in Portland Press Herald/Maine Sunday Telegram on Feb. 9, 2014