So You Want to Be an Oyster Farmer? A Chat with Jason Wilford

From selling ad space to shucking oysters, the career change of one man proves that life’s greatest pearls often lie outside of the comfort zone.

It is 2016, and Jason Wilford’s success in the print advertising business has allowed him to buy a home and lead a comfortable life. It’s what everybody wants, right? Well, sort of. The problem is Wilford is also feeling stuck and unfulfilled. So he plays hooky one day with a friend who has a boat. It just so happens that the friend, Matt Pluta, is a Choptank Riverkeeper (and their program director), plants a seed in Wilford’s thoughts. “You know, he told him, “aquaculture is a thing you should consider. Ever think about oyster farming?”

Although it was Wilford’s first exposure to that idea, over the next few months, he kept bumping into people who voiced similar sentiments. By January 2017, Wilford yielded to the hints the universe was sending. Two years of permits, loans, and planning later, he was ready. He even took ‘So You Want to Be an Oyster Farmer?’’ classes from the Chesapeake Bay Foundation. “I learned valuable lessons that have stuck with me,’ said Wilford, “such as ‘more flow, more grow, more dough.’ It’s about how much water flow can get to the oysters.” So he looked for places with good flow, and bought 125,000 seeds the first year, then 250,000 the second year. He wrote a sustainable business plan.

And then COVID hit and laughed at everyone’s plans.

As the world waited to see what was coming next, Wilford reached out to Kristi DeMartino, a close friend since high school. They’d kept in touch. She understood some of what he was going through and had experience on the water, having worked on an airboat in the Everglades and, most recently, on charters from South Beach. But her life, too, was on pause. “Come check out the oyster farm,” he asked.

And in August 2020, she did. “I came up to see his operation. And I thought this was the exact opposite of yachting in Miami: Getting on this oyster boat wasn’t like boozing and cruising. It was hard physical labor. I liked it.”

She liked it so much that she stayed, and the two became more than just business partners. Less than a year ago, the couple welcomed their daughter, Robin.

DeMartino’s involvement also added a softer component to the business known as Pirate’s Cove Oysters. She created a graphical logo of an oyster mermaid sitting on top of the world and a brand: Cosmic Mermaid Oysters Out of This World. It fits well with their philosophy of a dissatisfied pirate seeking adventure, finding his muse, and being brought together by oysters, a fun and healthy indulgence to be shared among friends. “Oysters brought us together,” says DeMartino, “and we believe they should do the same for others.”

Together, the couple’s energy is now focused on their five-acre farm where a half-million oysters are planted. Located on the Dorchester County side of the Choptank River, between Horn Point and Jenkins Creek, within the Sandy Hill Sanctuary, it is leased from the Department of Natural Resources. It’s a location, they say, conducive to growing tasty oysters.

Of course, once grown, making sure they get to the table can be expensive, but Wilford is up to the challenge, especially when he can count on a little bit of help. “From the crane to the tumbler, a lot of equipment on Pigg (their boat) is built by Jason and his friends,” says DeMartino. Wilford adds, “Outfitting it would cost well over $20,000, and that’s one good aspect of doing something kind of outlandish is that people want to help. And they think it’s really cool when they lend their expertise.”

Wilford also had the opportunity to put his construction skills to use when he added refrigeration to a trailer for one of the first events they did with their newly harvested oysters–the Cordova Balloon Festival. “We had $4 in our bank account at that time,” DeMartino said. “We did the three-day event and went through probably 10 bushels. We both learned how to become really good shuckers!”

It led to an unexpected niche as they found themselves in demand at private events such as parties, weddings, etc. “We’ve joked about our carnival lifestyle, traveling with a refrigerated trailer to beer festivals and things. We hadn’t planned on that originally, and it’s been worth it,” said DeMartino.

But Pirate’s Cove Oysters is also known much closer to home. Chances are, if you shop at the Easton Farmer’s Market, you’ve sampled their oysters and hung out while they grilled or shucked their harvest. They’ll be there again with a strong focus on the future when the Farmer’s Market opens for the season this weekend. “In the grand scheme of things,” said DeMartino, “we plant a small amount. There are other farms that plant millions. We try to keep it small because we see our oysters as a boutique experience to be enjoyed with your friends.” “Plus, we just have fun doing it,” added Wilford.

So for now, the business checks all the boxes, says DeMartino: “We both like being on the water; there’s a certain romance to it. We enjoy problem-solving. We love talking to people at the farmers market and establishing relationships that way.”

More important, though, is what this company means to the family legacy now that they have a daughter. “We want to have Robin grow up with parents who love what they do and teach her to do what she loves,” said Wilford. Everything changed with Robin’s arrival, he admits. “It’s hard to look back on what I thought it would be versus what it is now. I mean, it’s a million times better, but I can’t remember what I thought at the time.”

We started this story by mentioning that life’s greatest pearls often lie outside the comfort zone. For Wilford and DeMartino, oyster farming is not just a job. But in case they forget, Robin will be there to remind them. After all, her middle name is Pearl.

You can reach Pirates Cove here.

Val Cavalheri is a writer and photographer. She has written for various publications, including The Washington Post.  Previously she served as the editor of several magazines, including Bliss and Virginia Woman. Although her camera is never far from her reach, Val retired her photography studio when she moved from Northern Virginia to the Eastern Shore a few years ago.. She and her husband, Wayne Gaiteri, have two children and one grandchild.