ARTIST PROFILE
Elizabeth Whelan
Painting The Stories Of Lives, Waters, And Resilience
By Diane Alter
For Elizabeth R. Whelan, painting is more than a craft; it’s a medium for storytelling, connection, and preservation. Based in her studio on Chappaquiddick, Elizabeth's work captures the essence of her subjects–be they a waterfront tugboat, a storied CEO, or a cherished local artisan–infusing every piece with warmth and life.
Elizabeth’s artistic journey is rooted in her coastal adventures and her lifelong love for the water. A sailor at heart, she finds inspiration in the “working waterfront”–the boats, shipyards, and tugboats that fuel maritime life. This passion is also inspired by her partner, Bill Benns, a wooden boat builder whose craft mirrors Elizabeth’s dedication to detail and tradition.
“I’ve always been drawn to the waterfront and the stories it tells,” Elizabeth says. “There’s something timeless and deeply human about that connection to the sea.”
Her early artistic pursuits leaned heavily on graphic design and illustration, but a transformative pivot occurred in 2010 when Elizabeth decided to focus solely on painting. Two workshops–first with Daniel Greene and later Burton Silverman–helped her refine her skills and develop her voice as a fine artist.
For seven years, she and Bill lived as caretakers on Nashawena Island, a remote part of the nearby Elizabeth Islands chain. This off-the-grid existence, tending to a farm and Highland cattle, profoundly influenced her art, instilling a respect for resilience and the beauty of simplicity.
Portraits as Personal Narratives
Although Elizabeth paints waterfront scenes, still lifes, and gardens, she found her niche in portraiture, where her business acumen and love for storytelling converged.
“I knew I could not paint just for the sake of painting,” she explains. “To make a go of this craft, I had to create work that resonated deeply with people–and portraits do that.”
Elizabeth approaches each portrait with a blend of technical skill and emotional depth. Her process begins with a conversation to learn about her subject. “I need to see how they tilt their head, how they smile, their eye movements, and even how they cross their legs,” she says. “These small details help me capture who they truly are.”
Portrait painting is the art of capturing a person’s likeness, personality, and essence in a visual medium, typically on canvas or paper. As Elizabeth explained, portrait painting is as much about technical skill as it is about intuition and empathy, making it both a rewarding and demanding discipline in art.
One of her favorite commissions was for the retiring CEO of Tiffany & Co. Subtle “Easter eggs,” like iconic Tiffany jewelry floating in the background, imbued the painting with personal significance.
Another memorable piece was A Break in the Storm - Gannon & Benjamin Marine Railway. This black and white painting depicts the famed Vineyard Haven boat shop in the winter of 2008. The old shop truck was a common sight around Vineyard Haven in those days, ferrying lumber to and fro. And the second boat pulled up on the railway, its dark hull barely visible, was Elizabeth’s own Bristol 33.
Two of Elizabeth’s most treasured works are of boatbuilder Nat Benjamin, co-owner of the Vineyard’s Gannon & Benjamin Marine Railway, and of Island fashion designer Stina Sayre. Both trusted her enough to unveil their portraits publicly at an Island gallery without having seen them first.
Nat’s portrait remains so iconic that Elizabeth uses it on the back of her business cards.
Currently, Elizabeth is working on a bold new project: painting nine local actors in their favorite theatrical roles. This series will debut in the summer of 2025, showcasing her knack for combining storytelling and artistry innovative ways.
When asked about challenges she faces living and working on an island, Elizabeth quipped, “Thank goodness for FedEx.”
Resilience in the Face of Adversity
While Elizabeth’s career flourished, her family faced a deeply personal challenge. For more than five years, her brother, Paul Whelan, was unjustly held in a Russian prison. Elizabeth and her family fought tirelessly to bring him home, making 29 trips to Washington, D.C to keep his case in the public eye.
Paul, a former U.S. Marine, became widely known after his arrest in Russia in December 2018. Accused of espionage, Paul maintained his innocence, asserting that he believed the flash drive he received contained vacation photos. In June 2020, he was convicted and sentenced to 16 years in a Russian labor camp–a conviction decried internationally as politically motivated.
Paul endured harsh conditions, including isolation and substandard medical care, during his time in cus-tody. Reflecting on the ordeal, Elizabeth said, “No one is ever going to care as much as a family member does.” When Paul was about to be released in a negotiated prisoner exchange Elizabeth appeared alongside President Joe Biden in the Oval Office that day and spoke to Paul as he prepared to return home. Elizabeth, along with the President, was allowed to greet Paul on the tarmac at Joint Base Andrews, Biden removed an American flag pin from his lapel and pinned it on Paul’s jacket.
Now safely back in the U.S., Paul’s return has allowed Elizabeth to refocus on her art. “It’s amazing what we can do with our two hands,” she says, a sentiment that resonates deeply in both her paintings and her life story.
A Legacy of Connection and Craft
Elizabeth’s work extends beyond her own easel. Her YouTube channel offers instructional videos, blending technical tips with her warm personality to reach a broader audience. And this coming year, she will be launching a series of online painting and drawing workshops to help aspiring artists move forward in their own art practice.
Teaching comes naturally to Elizabeth–it is another of her many talents.
It is clear that Elizabeth loves what she does, loves people, loves her family, and loves Martha’s Vineyard. Collectively, these passions shine through in every piece she paints.
Whether she’s painting a retiring CEO, a coastal tugboat, or a Highland cattle farm, Elizabeth R. Whelan captures the essence of her subjects with authenticity and care. Each brushstroke tells a story, ensuring her work will resonate for generations to come.
For more information or to see more of Elizabeth’s work click: elizabeth-whelan.com, e- mail: erwhelan@gmail.com
Check out her YouTube channel for instructional videos at: www.youtube.com/@Elizabeth Whelan-artist