Captain Howland S. “Scotty” Roberts Jr., a Chesapeake Bay pilot who spent more than four decades guiding ships up and down the bay from Cape Henry, Virginia, to Chesapeake City, died from gastrointestinal bleeding June 25 at the University of Maryland St. Joseph Medical Center in Towson.

The Cockeysville resident was 81.

“We spent 40 years working together and Scotty was well-liked by all of the pilots. He had an upbeat personality and was always ready and willing to help people,” said Capt. Brian H. Hope, who retired in 2013. “He had an excellent reputation as a ship handler and pilot, and if you can say that in this profession, that’s all that needs to be said about a guy like Scotty.”

Howland Scott Roberts Jr., son of Howland S. Roberts Sr., also a Chesapeake Bay pilot and president of the Association of Maryland Pilots, and Dorothy P. Roberts, a homemaker, was born in Baltimore and raised on Taplow Road in Homeland.

A 1961 graduate of St. Paul’s School for Boys, Capt. Roberts attended the University of Baltimore, where he played Division I lacrosse, for two years.

After completing what he called “Coast Guard boot camp in 1964,” in an autobiographical sketch, he was assigned to the association’s pilot station boat at Cape Henry, Virginia, where he identified inbound and outbound shipping at the Virginia Capes.

Capt. Roberts was the fourth generation member of his family to become a Chesapeake Bay pilot.

Daniel T. Mathaney, an ancestor, was a founding member of the Association of Maryland Pilots in 1867, while another ancestor, William F. Mathaney, joined the association in 1872. His father became a member of the association in 1929, and later its president.

Capt. Roberts’s apprenticeship continued until 1966 when he earned his pilot’s license.

When he began his career, general cargo ships were 400 to 700 feet long with a 30-foot draft, a measure of how deep the ship sits in the water.

But that changed a few years later, when ships, some of them container vessels, ballooned to more than 1,000 feet in length with 44-foot drafts.

“These large, heavy-laden container ships in the C and D Canal [Chesapeake and Delaware Canal] were responsible for some of my more challenging times,” he wrote. “The ice in winter in the canal was always a thrill before satellite navigation. We made our turns into channels using trees and houses as guides. Despite the challenges of the canal, it was always my favorite assignment.”

Capt. Roberts had plenty of sea tales from his career. There was the time during the Cold War when he was aboard a Russian container ship bound for Baltimore, late on a warm June night, when all of a sudden he was surrounded by “very loud cracking sounds,” he wrote.

“Immediately, sirens began to wail, and I saw the officers and seaman running around wearing riot gear and taking their battle stations. I had no idea what was happening,” he continued.

“The mate who was most fluent in English explained to me that the ship was under attack. It was then that I realized that the loud cracks I had heard sounded like guns being fired at the hull of the ship.”

The canal dispatcher called the Chesapeake City police who resolved the problem. They found two extremely drunk hunters with .22-caliber rifles who thought it would be great sport to shoot at a moving vessel.

Meanwhile, Capt. Roberts found himself on the phone with the Russian ambassador to the U.S. after the ship’s captain called a marine operator in Wilmington, Delaware.

“I explained to him and assured him that the drunks meant no harm,” he wrote. “Thus, an international incident had been avoided, and the ship then had a Coast Guard escort all the way to Baltimore.”

His wife, Dr. Polly Benbow said he “loved every single minute of his job.”

“He didn’t mind the 4 a.m. calls or going to work during blizzards,” she said.

Capt. Roberts retired in 2008.

“I would love to be still working today, but Father Time takes a toll on pilots, mainly because of the demands of the job,” he wrote.

While he may have given up his profession, Capt. Roberts still liked taking to the sea aboard his 28-foot boat, The Wet Dream, for deep sea fishing expeditions.

“He was an avid deep sea fisherman and especially loved marlin fishing,” his wife said. “He also loved sailing The Wet Dream to Ocean City and Cape Hatteras, North Carolina.”

In retirement, he spent a decade volunteering and driving a shuttle bus at Greater Baltimore Medical Center.

“He was always upbeat and positive and didn’t want a funeral,” his wife said.

Plans for a celebration of life gathering are incomplete.

In addition to his wife of 43 years, a retired pediatrician, Capt. Roberts is survived by a son, Derek Scott Roberts, of Bel Air; and a sister, Jeanne Roberts Mangus, of Surf City, North Carolina.