Walter was the great-grandson of Woodberry’s founder, Captain Robert Stringfellow Walker, the grandson of legendary headmaster J. Carter Walker, and the son of an alumna, Helen Walker Craigie. He was the youngest student to enroll at Woodberry Forest in 1943. A scholarship student, he served on the monitor board, The Fir Tree (yearbook) board, and The Oracle (newspaper) board. He was a member of the German Club and the choir, and he pitched for the varsity baseball team, ran winter track, and managed the football team.
 

Upon graduation he entered Princeton University, where he majored in economics and minored in history. After serving in the US Marines during the Korean conflict, he attended Harvard Business School, where he met Berenice “Beese” Dennison, a Smith College graduate, whom he married in 1957.

The Craigies returned to Virginia, where Walter worked for F.W. Craigie & Company, a municipal investment firm, and the couple reared two daughters. Walter advised governors on financial and budget issues, worked on the Virginia Debt Capacity Advisory Committee, served on the Washington Airports Task Force Board, and held the offices of state treasurer and secretary of finance for the Commonwealth of Virginia. He left public service to work for Wheat First Securities and later, for Morgan Keegan & Company.

Walter was involved with many nonprofit organizations, including St. John’s Church Foundation, MCV Foundation, and the Montpelier Foundation. He also served as a trustee for Randolph-Macon College, his great-grandfather’s alma mater, which awarded him the doctor of laws degree in 2008.

Walter became actively involved with Woodberry Forest School in the late 1970s, when he advocated for the establishment of endowment funds that would provide the school with a permanent source of income. He served as a trustee from 1983 to 1999 and as chair of the board of trustees from 1994 to 2001.  In 2002, he was awarded the J. Carter Walker Award, the highest award Woodberry bestows.  Under his leadership, the board established an innovative "triple-R" fund, which directed a percentage of each capital gift toward a fund to care for the given capital project.  Woodberry's RRR Fund stands as a model for schools today.

“I will miss Walter dearly,” said Sion Boney III ’74, chairman of the board of trustees. “He was a magnificent man, a brilliant board chairman, and an unwavering, lifelong leader and champion of Woodberry Forest. His vision, dedication, foresight and attention to detail are legendary among Woodberry trustees.  Walter has been a mentor to me over the past twenty years and a constant sounding board for wise advice and counsel.  Woodberry is very lucky to have had Walter's undying love and attention across many decades of tireless service.”

Walter was also a generous donor. In  addition to establishing planned gifts to benefit Woodberry, he and Beese committed more than $1 million to the Our Strong Band campaign, which he served as a vice-chairman. The couple’s gifts were directed toward a scholarship and a mastership.

“Walter Craigie was a genuinely good man,” said Dennis Campbell, Woodberry’s eighth headmaster.  “He was an incurable optimist about the stock market, the economy, the church our country, and the world.  His legacy to Princeton, Orange, Richmond, and the Commonwealth of Virginia will endure, but his love for Woodberry was greater than them all, with the exception of Beese and his wonderful family.” 

"Walter's love for and dedication to Woodberry Forest are unsurpassed,” said Headmaster Byron Hulsey ’86. “His fierce loyalty, wise counsel, and sheer devotion to his alma mater have made the Woodberry community better at every turn. We will miss him greatly and be always indebted to him."

A memorial service will be held at St. Stephen's Church in Richmond, Virginia, on Saturday, March 12, 2016, at 2:00 p.m.