Robert Cassidy, air traffic controller and tower manager at Martha’s Vineyard Airport, retired last week after 14 years of service on the Island.
Mr. Cassidy began working on the Vineyard in 2012, spending seven years as an air traffic controller before being promoted to tower manager, where he has had a front row seat to the busy airport.
“It hasn’t changed significantly, except for the size of some of the private airplanes,” he said. “The private jets are getting bigger and bigger.”
Mr. Cassidy began his career in the Air Force, where he trained to become an air traffic controller. His assignments took him all over the country, from Mississippi to N.J. to Oklahoma City.
After leaving the Air Force, he became a civilian air traffic controller. His first assignment was in Warwick, R.I., where he worked until he turned 56, which is when the FAA requires that air traffic controllers retire.
But Mr. Cassidy wasn’t ready to stop working.
“I felt I was a little bit too young to stop working at that point,” he said. “Some people like it, but I wasn’t ready to retire at 56.”
He applied to a company that provided contract air traffic control services to the government. They happened to have an opening on Martha’s Vineyard.
The Island was already somewhat familiar to Mr. Cassidy. His brother, Michael Cassidy, had been a longtime resident of the Vineyard, and Mr. Cassidy had spent six months on the Island during the winter of 1981 while awaiting his FAA acceptance.
Mr. Cassidy shared that he enjoyed the challenges the job presented, particularly during the Island’s busiest season.
“In the summertime, all the traffic ramps up, and we have lots of airplanes,” he said. “It gets sort of challenging, challenging and exciting, and you get a better sense of worth for what you’re doing.”
Another challenge he faced was his commute, traveling weekly from his home in Warwick to the Island. Every Monday morning, Mr. Cassidy drove to Woods Hole, caught the ferry and worked five days on the Island. After his Friday shift, he returned home for the weekend, before starting over again on Monday.
Now, after years of working and commuting, he is looking forward to spending more time with his wife, children and grandchildren.
“I’m really into gardening, and I love my yard work and taking care of my property. That’s something my wife and I like to do together,” he said. “I have a daughter and three grandchildren in Rhode Island, and I’d like to spend more time with them and see them more.”
Looking back on his career, Mr. Cassidy said he feels fortunate to have found work he genuinely enjoyed.
“I think I’m lucky that I had a profession that I enjoyed because over the years, I’ve talked to a lot of people in different professions that don’t really enjoy their jobs,” he said.
This article appears in October 2 2026.