The Residents of Londonderry: Bob Woods


One of the many questions you could ask Bob Wood about his exceptional life is, “how in the world did a graduate of West Point end up teaching Navy Midshipmen how to sail?”

It’s a great story.

When Bob Wood transferred from Brown University to West Point in 1941, the United States had yet to enter WWII. As the reality of going to war set-in as their school careers progressed, he and his classmates were excited and anxious to serve.

Bob Wood graduated from the United States Military Academy at West Point in January of 1943 in the top quarter of his class. This is significant as 1943 was the only year where there were two graduating classes. With the United States fully committed to WWII, it was critical to get soldiers overseas as soon as possible.

Bob entered the Army Corp of Engineers following graduation and completed additional training at Ft. Belvoir in Virginia. He was later assigned to the 7th Armored Division known as the “Lucky Seven.”

As Bob and his fellow soldiers were on the Queen Mary in New York getting ready to head overseas, the troops received news of the D-Day invasion of Normandy on June 6, 1944. When they landed in Scotland, they traveled through Southern England and then joined-up with the Army in France and stayed through the conclusion of the War in Europe.

Following V-E Day in May of 1945, Bob remained in Europe for the next few years and was stationed in Germany to assist with the Corp of Engineers’ rebuilding efforts. His wife, Cynthia, or “Cynnie” met him in Germany and they took up residence in a resort community in Bavaria where they lived in the house of a former Nazi officer. Their first daughter, Michael, arrived soon after, and Cynthia’s mother also joined them to help with the baby.

The young family returned to the United States and Bob left the Army and took a job in Chicago. Shortly after, he was called back to West Point to join the General’s Staff to help run the school as other officers had been sent overseas to serve in the Korean War. Cynthia and Bob welcomed their second daughter, Cindy, during their time in West Point.

Following the Korean War, the Woods returned to Chicago and then moved with Bob’s career – living in New York and the New Jersey where their son, Robert Jr., called Casey, was born. Bob worked as a consultant on Wall Street for many years while he and Cynthia raised their family.

Bob and Cynthia later relocated to Annapolis when Bob accepted a new position in Washington D.C. Both Bob and Cynthia were avid sailors and enjoyed being on the water.

Following Cynthia’s death, Bob remained in Annapolis and later met his second wife, Frances.

During his time in Annapolis, Bob became a sailing instructor with the Naval Academy, a role he enjoyed immensely. While Bob didn’t boast about his Army career, he was eventually discovered when a Midshipman caught sight of his class ring and realized a West Point graduate was teaching them how to sail!

After more than a decade in Annapolis, Frances convinced Bob to move to the Eastern Shore, an area she had grown to love with her first husband, and they settled in St. Michaels in the 1980s. They enjoyed and active retirement and continued sailing.

Frances passed away in August of 2014 and Bob remained at their home in St. Michaels until he moved to Londonderry in September 2015. He continued sailing until just recently.

This past May, Bob attended his 75th Reunion at West Point with his two daughters where he was joined by another classmate, and the families of several others. They also took some time to visit their old homes in New Jersey and New York as they made their way back to Easton.

Bob will celebrate is 98th birthday this month and is a proud father, grandfather, great-grandfather and veteran.

Letters to Editor

  1. Tonya Finton says

    My parents, then my family and I, enjoyed a wonderful friendship as neighbors to Bob and his wife Frances in St. Michaels. When my father passed away they could be counted on to include my mother in evening sails and the occasional cocktail in their home. From taking us sailing on Solitude to always having dog treats in his pocket for our pets, they don’t get any better than Bob Woods!

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