Otto Trott is a celebrated Bermudian artist who has won numerous awards for his paintings.

This year alone, he won an award for design and composition in the Charman Prize art competition at Masterworks and The Chesley Trott Cedar Award in The Serjeant’s Cup Marine Art Prize exhibition at the Bermuda Society of Arts Gallery in Hamilton.

Still, the 70-year-old has moments of doubt about his work.

In his latest BSoA art show, Bermudaful Heritage, his painting End of the Race depicts comet sailboats floating in the midst of seaweed.

“I don't know if I really captured what the seaweed looks like,” he said. “I had to achieve a balance between the tone of the seaweed and the colourful boats. And some of the seaweed was above the water and some below it, to add to the challenge.”

The oil painting is part of a series he has done showing different aspects of the Edward Cross Memorial Long Distance Comet Race.

In this 80-year-old race started by the West End Sailboat Club in Sandys in 1944, people race comet sailboats from one end of the island to the other, each year alternating the start between St George’s and Sandys.

Mr Trott fears the race is being overshadowed by other events, such as the Revel De Road Carnival, which also happens on National Heroes Day in June.

“People on the North Shore used to have their chairs out in their yards watching the race,” Mr Trott said. “Now they have their backs to the water, while they wait for Carnival.”

He wanted the pieces to reflect how popular the race once was.

“It was almost like Cup Match,” he said. “People would line the rocks to watch. There were also people watching from boats.”

Today, people still come out to watch, but the crowds are not as big as they once were.

“It is something that should be kept going,” Mr Trott said. “I don’t want it to die down to where it is just enthusiasts watching.”

He has been a fan of the race since childhood, when his uncle Alton Millett was a top sailor in his boat Kitty Hawk II, winning the competition 11 times between 1955 and 1983.

“He was my uncle by marriage,” Mr Trott explained. “I never took part in the race as a competitor, but one year I followed my uncle in another boat, as a spectator. It was a windy day, and I only managed to go a short distance before I decided it was too rough to go any further.”

He remembers when in 2011 only one boat finished.

“It was a very rough and windy day,” he said. “Many boats either had damage like broken rudders or broken masts or they sank or capsised.”

The Royal Gazette reported that Rockal Evans won the race by “managing not to sink too often”.

“His crew was Benn Smith who was ten years old at the time,” Mr Trott said. “Benn was this year's winner, with Christian Ebbin as crew. He has won the race a few times.”

Mr Trott can see the boats going by his home in Hamilton. Once they are gone, he usually rushes to the next vantage point, and the next.

“Many people do this, and there is often traffic,” he said.

Gates Fort and Fort St Catherine in St George’s are popular viewing spots to watch the race in the East End.

“This year the race day was windy, so the race was quick,” he said. “Plus they have changed the layout of the road because of the St Regis Hotel. By the time I got to Fort St Catherine, I missed the boats.”

One of his paintings shows a line of men helping to bring a comet boat out of the water next to King’s Square in St George, after the contest.

“When the boats finish, people pull the boats up a ramp by a rope,” Mr Trott explained. “There was a pulley to help, so they do not have to rely entirely on brute strength. I was pulling on that rope before some other people came along and started helping. I stepped back to take a photograph.”

For reference, he used photos he took of the sailing race over a ten-year period.

In some art circles painting from photos is frowned upon, due to fears that the camera alters colours or distorts proportions.

Mr Trott was not particularly concerned by these things, saying he has been painting long enough to know how to mix colours.

“Of course, it is always better to paint from life,” he said.

However, he has found that digital photography can be a help, exposing and filtering colours to show different details of the scene.

In addition to the paintings of the Edward Cross Memorial Long Distance Race, he also has watercolours in the show of historic homes and landmarks in Bermuda, and even some flamingoes at the Bermuda Aquarium and Zoo.

“The flamingoes are usually some distance away in the pond,” he said. “One day I went to the aquarium and the birds were right up against the fence. That is how I came to paint that one.”

Last year, he received a Bermuda National Trust Cultural Heritage Award for documenting Bermudian life in his art. He started focusing on the island’s culture, because he felt it was not often realistically depicted in Bermudian art history. His ambition is to fill that gap. He now has a YouTube channel where he explores local history and culture, and talks about his art process.

• Bermudaful Heritage is on at the BSoA at City Hall in Hamilton until November 12