Watercolor wonder

Artist Alan Hampshire literally paints the town.


A lost cat helped to determine the artistic path of watercolorist Alan Hampshire. The prolific artist had spent two years painting scenes around Vineyard Haven with a mission to capture the entire town in watercolors. While living on his boat in the Hines Point area, he completed dozens of images of homes and buildings around the town. This past May, Hampshire’s cat, Ashton Kutcher, disappeared, and Hampshire realized that the only possibility was that his pet had fallen overboard. The distraught artist spent two hours circling the area in the boat, with no success. He posted missing cat signs around the Island, in the hopes that Ashton had swum ashore.

“I would go to Oak Bluffs to escape my heartbreak,” says Hampshire. “Every night I was crying and looking for him.” During the day Hampshire was also painting — capturing scenes around the town he had retreated to in his sorrow. Exactly two months after Ashton Kutcher disappeared, Hampshire spotted him sitting under a Lost Cat poster in Hines Point. The cat was a bit worse for wear, but had managed to survive. “It was my birthday,” recalls the artist. “I was praying that that would be my birthday present.”

Hampshire, who has since moved to a more terrestrial living situation, has continued painting scenes around Oak Bluffs, and during the month of December he will exhibit his watercolors of iconic town scenes at Mocha Mott’s. Of his switch of subjects, Hampshire says, “It was sort of a karmic nudge. Oak Bluffs is my favorite town. It’s colorful. It’s Byzantium. I was sort of keeping Oak Bluffs in reserve to cheer myself up someday.”

In the same manner that he had become well known around Vineyard Haven, the eccentric artist has become a fixture in Oak Bluffs over the past few months. Hampshire prefers to paint onsite, carrying his watercolors around and setting up in front of a shop or business while he paints. He enjoys the interaction with passersby. “I think of myself as artist-shaman,” he says. “I sort of inspire people. I’m part of the local flora and fauna.”

In 2016, Hampshire showed his Vineyard Haven paintings at Mocha Mott’s in that town. Now the artist will be debuting his new paintings, appropriately, at the Mocha Mott’s location in Oak Bluffs.

Hampshire favors bright colors, and he employs a lighthearted, almost whimsical style. For the Mocha Mott’s show, he’ll exhibit images of the Flying Horses and Union Chapel, as well as various local shops and restaurants. Everything on display will be available for purchase at $200 each.

Before moving to the Vineyard full-time in 2007, Hampshire carved out a successful career for himself as an artist in New York City. His résumé is both varied and impressive. In the 1980s, he earned artwork commissions from a number of the most well-known nightclubs of the day, including Limelight, Palladium, and Area. He was among the group of popular outsider artists in New York in the 1980s that included Keith Haring and Basquiat. Hampshire also pursued a number of other art-related careers while living in New York. He worked variously as an art dealer, a food stylist for Macy’s, and a jewelry designer. He created accessories for Patricia Field, and worked in publishing. He worked for three museums and four galleries.

His style, as well as his choice of media, has changed over the years. “In New York people said, ‘You paint nothing but sex and death,’” says Hampshire. Part of the reason that he came to the Vineyard originally was that many of his friends were dying of AIDS. At some point, the artist’s vision became considerably brighter. Although he originally worked in oils, Hampshire’s switch to watercolors represents the third medium he has experimented with. A native of Idaho, the artist got his first break when he won second place in a contest sponsored by the Pastel Society of America. He used the prize money to study at the Art Students League of New York.

The portability of watercolors has worked well for Hampshire’s gypsy approach to painting. He likes to set up shop wherever he finds inspiration, and paint his chosen subject at one sitting. “I always think of it as performance art,” he says. “The whole town is my studio. I interact with the people.”

One recent encounter led to a partnership of sorts. He met Tony Santos while wearing one of the house painter’s Tony’s Painting sweatshirts — a thrift shop find. Since then the two men have forged a relationship whereby Santos provides Hampshire with logo wear and small donations. The artist refers to him jokingly as his corporate sponsor. Hampshire painted a picture of Santos’ van, and was featured in a promotional video.”He’s given me street cred,” says the artist of his sponsor.

“I’ve devoted my whole life to my art,” says Hampshire. “I think I could spend the rest of my lifetime painting the Island.”