Stephen Engley explores his Island roots through art.


Artist Stephen Engley’s family left the Vineyard when he was only 3 years old. Three decades later, after growing up in the Boston area and studying art and history in Philadelphia, Engley has returned to the Island, and is exploring his roots and the history of the Vineyard through his art.

“I was born on the Island, but I don’t remember it,” he says. “My brain is trying to connect with the past through my drawings. Like we all do, I’m trying to turn back the clock and figure things out.”

The results of this sort of self-exploration are on view to the public in the form of a series of paintings on display at Mocha Mott’s through the end of the year. The 10 images currently hanging on the Vineyard Haven coffee shop walls include both historic views of scenes around the Vineyard and illustrations of old cars, trucks, and boats. The images, which are priced from around $200 to $900 (for a large painting of the Gannon and Benjamin Boatyard) include frames handmade by carpenter Danny Moraga.

“My grandfather was an engineer,” says Engley, “and I grew up drawing planes, boats, and cars. It’s a theme that keeps popping up in my work again and again.”

Examples of the vintage vehicle images include a painting of a handful of trucks in a parking lot with the long shadow of winter-bare trees cast over the scene. Engley based the painting on a photo he took at Conroy’s parking lot in West Tisbury. “I liked the tension of it,” he says. “There’s beauty and tension at the same time.”

The historic images are based on old postcards and other photos from the past. For example, one painting shows a corner of downtown Main Street in Edgartown with an A&P grocery store in place of the building that now houses the Port Hunter. There are a few people out front dressed in 1950s clothes, and, of course, a couple of old cars parked on the street. Another image shows the Steamship Authority building in Oak Bluffs from the turn of the 20th century. Visible in the painting are the vestiges of the train tracks that once ran between Oak Bluffs and Edgartown.

“I’ve always wondered what the Island was once like, and what it could become,” says Engley. In other work he also covers a wide range of subjects, from landscapes and traditional interior scenes to abstracts to imagined fantasy scenarios. For his next project, Engley plans to create tiny dioramas of Vineyard scenes and then photograph them.

“I’ve been drawing on and off my whole life,” says the artist, who works full-time at Mocha Mott’s. “I’ve been pretty focused on my art ever since I graduated from college.”

Engley moved back to the Vineyard three years ago, partly to find his roots and to reconnect with family.

“When I moved here, it just changed my life,” he says. “I had family around me for the first time in a long time. My life’s been getting more and more cohesive since I moved back to the Vineyard. I’ve been investing in myself more and more.” Next spring, Engley plans to marry his fiancée, Casey Dobel.

Last fall Engley started a life drawing group, gathering in the Vineyard Haven apartment he shares with Dobel. Although the venture proved successful, it had to be put on hold indefinitely due to pandemic restrictions. However, Engley hopes to eventually start the group up again. “Life drawing gives me everything I need in art — the discipline and focus, and the challenge of drawing the human figure,” he says. “It also brings the community together.”

Mocha Mott’s, Main Street, Vineyard Haven, 508-693-3155, mochamotts.com.



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