Windjammer Days

United States Navy

Not self, but country. Always courageous.

As Boothbay Harbor prepares to celebrate the 64th Annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles highlighting local Navy service members—sharing their stories, experiences, and the lasting impact of their service. These articles are a tribute to the men and women whose commitment to duty reflects the maritime heritage at the heart of Windjammer Days and the deep appreciation of our community.

Each of our schooner sponsors have chosen a U.S. Navy member to honor during Windjammer Days. Below are their stories.

If you would like to meet some of the U.S. Navy member, mark this date on your calendar, for an informal Meet & Greet on Monday, June 23rd, 3:30-5:00 (location to be determined). 

Dr. Barclay M. Shepard Ensign, USNR, United States Maritime Service (Post World War II) and Commander, Medical Corps United States Navy (Vietnam War)

I’ve had the incredible fortune of being at the right place at the right time throughout my 100 years on this earth and some of my greatest memories come from my military experience. I served in the Merchant Marine just after the end of the Second World War aboard an American Export Lines ship from June 1946 thru May 1947, transporting supplies from the United States and to and from various ports in the Mediterranean, Russia, India, Pakistan, and Burma. I sailed aboard the S.S. Coeur d’Alene Victory, one of the many Victory Ships which were built toward the end of World War II to replace the much slower and aging Liberty ships. Each Victory ship was named after a college or university. These were 10,000-ton cargo ships with a horsepower of between 65 and 80 thousand and a speed of between 16 and 18 knots. Click here to see the rest of the biography.

Steve Rosser

I joined the Navy right out of college. I graduated on December 19th 1981 and was in Officer Candidate School (OCS) on January 2nd 1982. Not really having a plan for what I wanted to do, I was enticed by the ads that I read seeking responsibility and a sense of adventure and travel. When I graduated from OCS, I became a Surface Warfare Officer (SWO) with my first job as a Missile Control Officer on a KIDD Class Destroyer USS CALLAGHAN (DDG 994), a ship that is still in active service in the Taiwanese Navy. On my first deployment, we accompanied the Battleship USS New Jersey (BB 62) with port stops all over Asia. I followed that with subsequent tours in Washington DC and onboard the USS CHANCELLORSVILLE (CG 62), an AEGIS Class Cruiser, as the Weapons Officer. Click here to see the rest of the biography.

Andy Benedict

I wasn't exactly inspired to join the Navy. I had no idea what I wanted to do with my life and didn't want to spend a lot of money at college to find out.  

I enlisted right after high school graduation in 1978 at 18 years old but didn't go to boot camp (in Orlando) until January 1st of 1979. Life was great back then. I actually enjoyed boot camp, for the most part. I was my first time in Florida, and it was nice and warm. It was a big culture shock, as I was coming from a very small town in Pennsylvania to all the diversity of the Navy. I really liked (and still do), the differences in the people from other areas of the country. Click here to see the rest of the biography.

William Carroll

What inspired me to join the U.S. Navy was a combination of patriotism, the desire for a true challenge, and the influence of two brothers from my hometown, Jason and Matt Higgins, who had gone before me into the SEAL Teams. Seeing people from our small community accomplish something so demanding showed me what was possible. Their example motivated me to follow in their footsteps and pursue a path that required complete dedication, resilience, and commitment to something greater than myself. Click here to see the rest of the biography.

Jay Quinn

After graduating from high school in 1980 I decided if I didn't find a good job by the end of the summer I'd join the Military. I was 18 and working at Zayre’s in Waterville Maine. Like any 18 year old at that time, I partied regularly and had a girlfriend. The reality was that I wasn't going anywhere and it was time to man up and do something useful with my life so I joined the Navy and volunteered for submarines. Click here to see the rest of the biography.

Jason Higgins

I joined the United States Navy at 17 years old because of a deep sense of patriotism and a belief that I had from a very young age: some people are put here to protect others and eliminate bad people from the earth. I always knew I would fight. I always knew I would stand up for what I instinctively knew was right. Click here to see the rest of the biography.