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RACHEL YOUNG PHOTO Kara Hoblin of Greenport adds text to a chalkboard display at First and South restaurant in Greenport last week. (Credit: Rachel Young)


Her fingertips stained a dusty shade of greenish-blue, Kara Hoblin used her forearm to rub her nose before selecting a piece of pastel chalk from an antique metal kit in the dining room at First and South in Greenport.

Standing on a wooden chair, the 25-year-old began coloring in the outlines of Christmas tree ornaments on the restaurant’s 22-by-12 foot chalkboard. Days before, she had spent close to 10 hours drawing a 1920s flapper outfitted in a luxurious red coat, her thin, two-dimensional frame surrounded by a snowy scene.

The festive drawing, she explained, was done for a holiday party being held at First and South later that evening. And Hoblin, who lives in Greenport, wasn’t donating her services: She’s one of a growing number of North Fork artists who make ends meet by creating custom chalkboard drawings for wineries and restaurants. Their creations typically advertise events, menus and special promotions and are often collaborations between the artists and business owners.

“This is my main source of income,” said Hoblin, who also does chalkboard art for a large number of other North Fork businesses, including Harbes Family Farm and Vineyard in Mattituck, The All Star in Riverhead and Vino & Vittles in Greenport. To make additional money, she also designs custom logos and signs for businesses, uses permanent chalk markers to create artwork for sale and often works weekends in the tasting room at Kontokosta Vineyards in Greenport.

“It’s all word-of-mouth,” Hoblin continued, pausing in her coloring to look over her shoulder. “It’s unreal.”

While Hoblin put the finishing touches on a Christmas tree at First and South, Pat Olstad of Cutchogue was busy at The Lenz Winery in Peconic, drawing an anthropomorphized reindeer family on the wall-mounted chalkboard there. Her drawing was to accompany a block of text promoting select vintages of chardonnay and gewürztraminer.

Pat Olstad of Cutchogue uses pastel chalk to draw a family of reindeer on skates at The Lenz Winery in Peconic last week. (Credit: Rachel Young)
Pat Olstad of Cutchogue uses pastel chalk to draw a family of reindeer on skates at The Lenz Winery in Peconic last week. (Credit: Rachel Young)

A painter by trade, Olstad said Lenz commissions her to draw chalkboard pictures at least four times a year.

“I was working at Lenz two years ago and the person who was doing the boards left,” she said. “And they asked me to take over.”

It’s difficult to pinpoint exactly when chalkboard art became a popular, fun way for businesses to communicate with customers. But the trend seems to have taken off in 2012, when Brooklyn graphic designer Dana Tanamachi used chalk to create memorable cover art for issues of Time magazine and O, the Oprah Magazine.

That same year, Tanamachi told the Wall Street Journal that chalk “was the perfect medium for my work. It’s cheap and easy to manipulate.”

Olstad and Hoblin agree.

“If you make a mistake, it’s easy to erase,” Olstad said. “It’s very forgiving.”

Like Tanamachi, who told the WSJ she accidentally discovered her niche while doodling on a friend’s chalkboard at a party, Olstad and Hoblin’s career paths have both been directed largely by happenstance.

When she moved to Greenport in May 2013, Hoblin explained, she met and quickly became friendly with Sarah Phillips, co-owner of First and South. Upon learning that Hoblin was an artist, the restaurateur asked if she’d draw something on the eatery’s chalkboard.

“We just wanted to use it as a concentrated message,” Phillips said. “You know how people like to rearrange their furniture? In a dining room, you don’t have as much power to do that. So the way we can constantly evolve and change along with the seasons is by dedicating artwork to whatever’s going on.”

Hoblin's 1920s flapper drawn entirely with chalk at First and South. (Credit: Rachel Young)
Hoblin’s 1920s flapper drawn entirely with chalk at First and South. (Credit: Rachel Young)

Hoblin, who studied photography at SUNY/New Paltz and has been drawing since she “was able to pick up a pencil,” was initially hesitant to agree to Phillips’ request.

“She was like, ‘You’re an artist. Can you do our chalkboard?’ ” Ms. Hoblin recalled. “And I was like, ‘Uh, no. I’ve never done a chalkboard. I don’t think I can do it.’ And she was just like, ‘Stop; give it a try’ … and I did it and it came out really good and since then, I’ve been doing it every month.”

At Lenz, tasting room worker Sean Tracy said the winery receives “a lot of positive feedback” about Ms. Olstad’s designs, which are fueled by her imagination.

“Before people notice our wine or displays they usually head straight toward the chalkboard and take a picture,” he said.

As Olstad used pink pastel chalk to fill in a female reindeer’s sweater, customer Anne Williams of San Francisco approached her.

“You do those?” she asked the artist, pointing to a previously completed drawing of a large polar bear with prickly fur. “That’s great.”

Despite the enjoyment their work brings to others, Olstad and Hoblin both said their biggest challenge is finding enough work to sustain themselves.

“Chalk is an outlet I’ve excelled at a lot and I really enjoy it,” Hoblin said. “Being a working artist is a struggle, but I’d rather be doing that and be happy and feel like the work I’m doing isn’t work.”

Back at Lenz, money wasn’t on Olstad’s mind at the moment. She had a job to finish.

“I still have to do the snow and I have to finish the reindeer family and the pond,” she said. “I’ll probably add more trees. I might add another reindeer; I’m not sure. I think I’m going to keep it simple.”

To see more of Hoblin’s chalkboard art, visit To view more of Olstad’s work, visit The Lenz Winery in Peconic, where she has paintings on display through the end of the month.

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