The sun is setting in this piece titled “Saybrook Point Lighthouse” as a schooner and a yawl make their way through Long Island Sound, taking advantage of the last bits of daylight. For maritime artist Loretta Krupinski Bailey, this scene is not a product of her imagination, but rather a depiction of the real seascape she found in front of her while sailing from Mystic Seaport to Essex on the Sylvina W. Beal, the oldest existing auxiliary knockabout fishing schooner in North America. “Anyone who’s been on sailboats can always remember one of the best sails they’ve ever had,” Bailey recalls. “It was beautiful, and we happened to arrive at the lighthouse around sunset.” Bailey, who paints from her own photographs, was carrying her camera on the sail and started taking pictures as they approached what is officially known as Lynde Point Lighthouse in Saybrook, Connecticut.

A native of Long Island, New York, Bailey has always lived on the water. She started boating at a young age on her father’s Lyman runabout and later moved to Old Lyme, Connecticut, where she started painting classic wooden boats on canvas. She often passed the lighthouse pictured here when she and her husband ran their catboat in and out of Long Island Sound.

After spending 20 years in Old Lyme, Bailey moved to Mid-Coast Maine, where she found a new subject matter for her paintings. “There were a lot of lobster boats, but not too many classic wood boats, so I started getting into the maritime history here,” she says. Working from old black and white photos from the Maine Maritime Museum and Penobscot Marine Museum, Bailey’s interest in the area’s history grew. Eventually, it culminated in the book Looking Astern: An Artist’s View of Maine’s Historic Working Waterfronts.

When doing historical paintings, Bailey has the advantage of being able to draw from her personal experience on the water, which makes up for the lack of detail in the early reference photos. “Having sailed myself, I know how boats are rigged and to look for the water movements and the wind,” she says, which breathes new life into old scenes. “The way I’ve been recording Maine history is not just as black and white photographs, but in real color.”

Bailey and her husband no longer own their catboat, but the water remains central to her life. She lives on a saltwater cove, and when she is not recreating historic barques and schooners on canvas, she still finds herself drawn to lighthouses. 

This article was originally published in the January 2022 issue.