Tom Nicholas, N.A.

John Terelak 

Alice Beach Winter

Robert Douglas Stephenson was born in Gloucester, Massachusetts on August 21, 1935, the first of two sons born a year apart to Charles Francis Stephenson and Cora (Douglas) Stephenson.  Bob grew up on Mansfield Street, attended school in Gloucester, won the Sawyer Medal for academic excellence, and graduated from Gloucester High School in 1955.  He then entered the U.S. army, and served until 1982, retiring as Sergeant Major after 27 years of active duty.  His long service carried him far from Gloucester, around the world to duty posts in Europe, the Mediterranean, and the Near and Far East.

Returning to Cape Ann in 1982, he began to pursue a lifelong interest in painting.  Study came first with John Terelak at the Gloucester Academy of Fine Arts, and then with Tom Nicholas, N.A. in Rockport.  This led Bob to seek his own art space in 1984.  He was soon the artist in residence at the fabled Fitz Hugh Lane House overlooking Gloucester Harbor.  The art spirit has taken him a long way since then.  He has been active in the art community, a member of the North Shore, Rockport and Hudson Valley Art Associations, The International Society of Marine Painters, and Academic Artists of America.  His work has received numerous awards, including a Gold Medal from the Academic Artists of America.  But, whether painting the river people of Southeast Asia, or capturing the spectacular vistas of the American West, Gloucester has always been his home port and favorite place to paint.

Now twenty years later, Bob spends most of his time in his Parsons Street studio just a stone’s throw from the Lane House.  Many have enjoyed his special vision of Cape Ann.  

How does Bob feel about life as an artist?  He summed it up this way, “I love Gloucester and Rockport, and have always been grateful to be a painter on Cape Ann.  It’s a great way to go.”




By Gail McCarthy, Staff Writer, Gloucester Times - July 19, 2012

Native son Robert Stephenson, a retired 76-year-old Army sergeant major, began delving into art as a 8-year-old boy when his mother took him to charcoal drawing lessons with noted American artist Alice Beach Winter in East Gloucester.

“That studio was a magic place and is, in part, why I am an artist today. It was filled with costumes and suits of armor,” he said of the studio his teacher shared with her husband, Charles Allen Winter, another noted American painter .

When he was a young man, more than 50 years ago, he painted a serpentine sea creature on a boulder at Cressy’s Beach.

In his 27 years of active duty, which took him to Europe, the Mediterranean, and the Near and Far East, he kept his drawing skills quiet in his own “don’t ask, don’t tell” mode.

“I haven’t been to Cape Cod but I’ve been through the Khyber Pass,” said Stephenson of the mountain pass that connects Afghanistan and Pakistan.

When he retired, he began a second career as a painter, catching the attention of viewers for decades. Most recently, the owners of a new Rockport gallery, called iartcolony, were invited to see one of his paintings by a friend of the artist and were stunned by the originality of his work.

“We had never seen anything like it. It left such an impression on us that we knew we had to see more. The work we found in Bob’s studio blew us away— our first instinct was that others needed to see these paintings. He captured the magical and mythical aura of Cape Ann, like no other. He is a truly visionary painter,” said Bob and Jill Armstrong, the gallery owners.

Stephenson paints landscapes, still life and figures. Many works contain minute images of people, giving perspective to the painting.

The public opening reception for this show takes place at the Rockport gallery, iartcolony, located at 42 Broadway, on Saturday, July 21, at 6 p.m.

Stephenson grew up on Mansfield Street, attended school here and won the coveted Sawyer Medal for academic excellence.

After he graduated from Gloucester High in 1955, he joined the Army, and soon after was shipped overseas

“I can get seasick looking at the water, but I have more sea time than some people in the Navy,” he joked.

His mother’s family has been here for more than 200 years. Her name was Cora Lincoln Douglas. “My grandfather was the first sergeant of Company G, the Gloucester Company, in the Grand Army of the Republic. He said he was going to name his first child after the president,” he said.

His recalled that his father, Charles Stephenson, was a navy commander, and a graduate of Annapolis naval academy. He later served in the foreign service, and died when Robert was 7 years old. The family had been living in Georgetown but moved back to Gloucester after his death. 

Much of Stephenson’s 27 years of service was spent in the East, which sparked his interest in Buddhism. His home and studio has an oriental flair and is filled with statues of the Buddha. His picture window on Parsons Street looks across the harbor. During a recent interview at his home, he pointed up to a white circular Chinese lantern, saying he needed to hang it because everything else in his living space is square.

One item of note in his home is his color palette, which he estimates to weigh more than 65 pounds.

“The day I discovered that the best surface on which to mix paint is other paint, is the day I decided I’m never cleaning the palette again. If it fell on your foot, you’d be crippled,” he joked.

After the service, Stephenson began studying under Rockport artist John Terelak, and has been mentored by another noted Rockport artist, Tom Nicholas. He later would become a teacher himself; one of the paintings in the show was created when he was teaching a class at the oceanfront at Bass Rocks when he decided to paint the class. The resulting image shows the expansive pounding surf dotted with artists at their easels.

At one point in his early career, Stephenson became the artist-in-residence at the Fitz Henry Lane House overlooking Gloucester Harbor, and he was active in the art community. He was a member of the North Shore, Rockport and Hudson Valley art associations, The International Society of Marine Painters, and Academic Artists of America. His work has received numerous awards.

Nicholas, who earned recognition as a National Academician, said Stephenson’s style defies a name.

“He’s a very original painter and a very intelligent man. He has his own way of doing things and he improvises his subject matter. He’s so unique that it’s awful hard to put a label to him. He’s adventurous and will try anything,” said Nicholas. “When he studied with me, I didn’t want to get in his way. When someone has their own way of doing things, it’s best for the teacher to stand back and not intrude.”


Art Critic and Montserrat Instructor Greg Cook has articles and journal entries that appear in The Boston Phoenix and The New England Journal of Aesthetic Research and Art New England magazine.

Greg Cook is the commodore of The Society for the Preservation of Fitz Hugh Lane, and founder of The Invisible Museum.  

Robert Stephenson’s Gloucester adventures

By Greg Cook, editor
The New England Journal of Aesthetic Research

Some years back we got curious about who had built the heavy wooden Asian-style gate and garden in an alley running down toward the harbor from Main Street in Gloucester, Massachusetts. It was a mystery. But after some investigation, we learned that the gate was the entrance to the studio of Bob Stephenson, a cantankerous old coot with an acid sense of humor who’d taken up painting after, he said, an injury prompted his retirement from the Army in 1982. Of course we became friends.

Stephenson—whose art is on view at iartcolony in Rockport, Massachusetts—had joined up after graduating from Gloucester High School (and painting a locally well known mural of a dragon on a boulder on Cressy’s Beach) in 1955. Career military, he traveled the world, served in Vietnam, and returned home after 27 years with the rank of sergeant major and a love of traditional Asian art. His studio was decorated with Buddhist shrines and Stephenson’s own paintings, which recall the heroic adventure illustrations of N.C. Wyeth (though more mushy in their execution).

Robert Douglas “Bob” Stephenson, 2012

Robert Douglas “Bob” Stephenson, 2012

Stephenson, now 76, is full of stories—about his tough mother struggling to raise him and his brother in Gloucester after their father died when Stephenson was just 7, about his exploits in the Army, about his annoying brother Richard, about his cantankerous old Aunt Eliza (when a doctor supposedly told the elderly lady that if she hadn’t been so full of bile “we would have been rid of you years ago,” she responded, “Who is this quack?”), about a Charles Addams-esque cartoon he published in The New Yorker decades back. As Stephenson describes it, the drawing showed a boy running to his mother who is busy at the kitchen sink. In his hand, the boy holds a skull. The caption: “Look what I found in Dickie’s head!” We can picture it in the magazine, but we’ve been unable to find it among the more than 68,000 examples included with the 2004 book and CDs “The Complete Cartoons of The New Yorker.”

Heart troubles have kept Stephenson from painting for several years now, but what remains striking about his art is that he often takes Gloucester locales and transforms the old fishing port into the site of pulp adventure tales. Half Moon Beach, around the point from Cressy’s in Stage Fort Park, becomes a cove where explorers might wash up. In other paintings, Stephenson stretches the towers and the steeples of the downtown skyline to transform the city into a medieval Mediterranean fortress town. Gloucester’s seafaring history already gives the community an air of gritty romance. Stephenson turns it into the place of dashing mystery and intrigue.

Robert Stephenson “Visions of Cape Ann and Beyond,” IArtColony, 42 Broadway, Rockport, Massachusetts, July 21 to Sept. 4, 2012.