Sisters take the helm at Westport’s Portside Restaurant

Third generation unexpectedly steps into new role at family-owned business

By Holly Riddle

Sometimes life doesn’t go how you expect. That was the case for sisters Kelsey and Alyssa Carroll at Portside Restaurant in Westport. The two grew up watching their grandparents, parents, aunt and uncle run the restaurant and Westport Marina. The two never had any intention of taking over the family business, but now that’s exactly what they’re doing. 

The change in heart came about when they heard a rumor that their father, James “Jim” Carroll, had sold Portside. 

“I called up my dad and I was like, ‘Excuse me. Why didn’t you tell us that you sold the business? We should be part of this discussion.’ My dad, in his very dry way, went, ‘Oh, what did I get for it?’ It was just a rumor,” said Alyssa.

She added, “It made me realize that if my reaction was that I was really mad that the business sold, then obviously I had a passion for it that I wasn’t recognizing prior.” Alyssa sent her sister Kelsey and brother-in-law Beck Simpson a long email that laid out what just happened. “I think I want to dive in and try to do the restaurant. I know that that’s something that you and Beck are considering doing. Could I do it with you?,” she wrote. They wrote back, “Yes, that was the missing piece. We had just needed an extra push.”

A family legacy

Kelsey and Alyssa’s grandparents Robert “Bob” Carroll and Diane “Dee” Carroll originally purchased the Westport Marina in 1982. Prior, Bob was a family medicine doctor and Dee was an art therapist. 

“We had purchased a houseboat and had to figure out what to do with it,” Dee said. “At the time, we lived near Albany, and the Hudson River was polluted, so we didn’t want to keep it there. So, one miserable gray Sunday afternoon in March, we drove up and checked out Port Henry, Westport and Essex.” 

“That car trip is something that’s still embedded in my mind,” added Jim. “Back then, this was the middle of nowhere. As an 8-year-old, it was horrific. I remember stopping into a little store that had stale bread and bad cheese, and that was what we were fed to stop us from whining.” 

After deciding on Westport as the perfect place to dock their new houseboat, Dee and Bob (and Jim, too, who came around) enjoyed the area for 13 years, before they finally had the opportunity to buy the marina. Along with the now-adult Jim and his brother Lawrence “Larry” Carroll, Dee and Bob embarked on the new venture. Eventually, Jim would go on to run the restaurant, then called The Galley, and Larry would run the marina (which he still does today, alongside his wife Lane). 

Humble beginnings

The family expanded the business’s offerings and services extensively. Dee admits the restaurant was a bit “primitive” at first. 

“We cooked hamburgers and hot dogs on the electric grill that we got for a wedding present,” she said. “We hand-cut our own potato fries and cooked them in the doughnut fryer my mother used. Each year, we did a little something different to improve. We got a couple real friers and a real grill, more refrigeration. It was quite an adventure.” 

Dee recounts one particular adventure that took place during the marina’s annual Lobster Fest, during which the restaurant could serve upwards of 750 lobsters and a thousand chickens. 

“I bought the chickens and had to take out the gizzards, rinse the chickens and get them ready to parboil. This fuzzy thing walked by [the door], I looked again and it was a skunk. I thought, ‘Oh no, please don’t spray.’ So—one heart, two hearts, three hearts. I fed the skunk every heart from those chickens. It kept him happy and we were great pals.”

Dee quickly handed over the restaurant to Jim, and Alyssa and Kelsey grew up around the business. Kelsey initially pursued a career in nursing, while Alyssa worked in film in Los Angeles before returning to the Champlain Valley.

“I’m really proud that it’s [a] three-generation [business],” Jim summed up. “We’re fortunate. We’re not perhaps the longest-running restaurant in Essex County, but we’re probably in the top five for a non-chain in the county. Places have come and gone and we’ve stuck it out.”