John Roberts Sherwood III

John R. Sherwood, III, of Annapolis, MD, passed away peacefully on April 12th, just short of his 87th birthday. John was born in Baltimore, the son of Virginia (Barrett) and John R. Sherwood. He grew up in Baltimore and spent summers on Gibson Island, MD, where he developed his lifelong passion for sailing.

John was a member of Gilman School’s class of 1954 and Dartmouth College’s class of 1958. After graduating from Dartmouth, he joined the Navy through Officer Candidate School. Following four years active duty, he served in the Naval Reserves as an intelligence officer for 16 years. Once his active-duty commitment to the Navy was fulfilled, John did graduate work in urban planning at the University of North Carolina and pursued a career in land use planning and real estate consulting. Over his career he worked with several firms including Hammer, Siler, George Associates; the Baltimore Economic Development Corporation; the State of Maryland’s Department of Planning, where he served as Deputy Secretary; Legg Mason’s Real Estate Advisory Group; and culminating with an Annapolis real estate consulting firm, Zuchelli, Hunter & Associates.

John’s true calling was sailboat racing, for which he had abundant natural talent. Starting at a young age on Gibson Island racing in LJ’s and moving on to Comets and Star boats, John had lots of success. He also sailed on his parents’ boat Gibson Girl. Later, his uncle, J. Miller Sherwood, recognized and nurtured his talent, inviting John to join the crew of his successful 40-foot Owens cutter, Rubicon. After college, John particularly enjoyed racing in the Star class, winning the Chesapeake Bay Yacht Racing Association’s High Point award in the Star several years. One of his proudest accomplishments was competing in the Star class Olympic trials in San Diego in 1968, where he placed 7th in a fleet that included several renowned talents. Earlier that year he placed 2nd in the South American Championships.

Adjusting to his growing family, in the mid ‘70s John took a break from the Star class and raced a Ranger 26, Witch of Pungo, and later a Metalmast 30, Witch’s Flower, in the MORC class, often with family forming the core of the crew. The family also cruised the Chesapeake in these boats, sharing lots of happy times with other members of the Gibson Island Yacht Squadron and the Sailing Club of the Chesapeake.

In the ‘90’s John raced a J/22, Double Nickel, out of Annapolis Yacht Club and especially enjoyed the club’s Frostbite and Wednesday Night race series, which he raced in for many years. He also returned to the Star class in the early-‘90’s, winning the 1996 Master’s regatta in Miami a couple of months before his 60th birthday. He remained active in the Star class until 2007-8, competing in many events on the Bay and in Miami. More recently, he raced Etchells and Harbor 20’s in Annapolis, Indians and International One Designs in Nantucket, and served as a volunteer coach for the Naval Academy’s Offshore Sailing team. He was inducted into the Annapolis Maritime Hall of Fame in 2000.

John was a lifelong member of the Gibson Island Yacht Squadron and Gibson Island Club. He was also a longtime member of the Sailing Club of the Chesapeake, Annapolis Yacht Club, Severn Sailing Association, the Naval Academy Sailing Squadron, and the Nantucket Yacht Club.

John is survived by his loving wife of 54 years, Lisa (Dobbin), daughter Anne (Otto Pohl), son Robert J. Kyle, Jr. (Melissa) and grandchildren Everett and Virginia Pohl and Madeline and Abigail Kyle. He was predeceased by his parents and sister, Sue Clark Sherwood.

In lieu of flowers, please consider a donation in John’s memory to Chesapeake Region Accessible Boating (CRAB), the Star Class Legacy Foundation, or the Annapolis Maritime Museum.

A memorial service will be held at 2 pm on Tuesday, May 2, 2023 in Saint Anne's Episcopal Church - Church Circle Annapolis, Maryland 21401.