Crooked Oak’s Head-First Dive Into Craft Spirits

In the corner of Crooked Oak Barrel Reserve’s soon-to-open Rockland, MA, tasting room is a unique conversation piece: an old, beat-up pickup truck. The exterior is mostly rusted, with some patches of light blue paint still intact. The grill has lost some of its shine. It’s aged, but still beautiful.

In a way, it’s a lot like the gin and vodka produced at the family-owned distillery, where James, Jonathan, and Melissa Mamary are putting a nontraditional spin on the classic spirits by aging them in oak barrels. What started as an experiment more than one year ago has grown into a full-fledged business, complete with multiple product varieties, a tasting room, and a growing legion of loyal drinkers.

It’s a picture the Mamarys might not have painted for themselves one year ago. James and Jonathan work full-time roles for their family’s business. They’d face a plethora of barriers moving Crooked Oak from idea to action. But as a family of entrepreneurs, they wouldn’t have it any other way.

“The definition of an entrepreneur is someone who takes an idea, runs with it, and makes it happen,” said Melissa. “When James and Jonathan first came to me with this idea, I thought it was wild. Crazy. But, now, we’re in market, people are enjoying it, and I’m thinking it doesn’t get better than this, right?”

“A year ago, we didn’t have a physical space, no business plan, no momentum. It was just James diving into a hobby, which had to become a business just to become a hobby,” said Jonathan.

He’s referring to federal licensure process, which requires applicants to already own their production equipment before submitting an application. For James to fully pursue his idea, he had to buy the equipment first and acquire a license before he even started experimenting.

But, that approach is old hat for James. “I tend to damn the torpedoes and go full-throttle into what I’m passionate about.” And, that’s what he did—turned his idea into a passion, then turned that passion into a product. And, Crooked Oak Barrel Reserve’s Gin and Vodka was born.

It’s a risk, backing into a business plan. But, entrepreneurs don’t shy away from risk; James, in fact, found thrill in the challenges: the unchartered waters of a brand new industry. The red tape and bureaucracy of navigating federal regulations. And, investing time, money, and effort into putting a hand-crafted spin on a classic spirit.

There are a number of distinct styles of gin, the common thread being a predominant juniper flavor. Many distilleries make gin from industrially manufactured alcohol they buy in bulk and redistill. London Dry styles—the Bombay Sapphires and Tanguerays of the world—contain all natural ingredients, and cannot have color or flavor added after distillation. Compound Gin—often the lower-priced varieties on the market—isn’t heavily regulated, but most have the juniper flavor added after distillation.

Crooked Oak’s spirits don’t fit these traditional molds. Their gin is aged in barrels. Not just any old barrels; they’re thoughtfully curated, with the end product—a truly unique flavor profile—in mind. Sourced from Mexico, the tequila barrel used to age their tequila variety for eight to 12 weeks gives the gin a hint of agave sweetness that pairs well with its natural botanicals. The result: after the initial wave of citrus hits your palate, an earthy, spice taste emerges. “Here’s where we set ourselves apart,” said Melissa. “Resting our gin in a tequila barrel brings forth the citrus notes, versus standard juniper-heavy varieties.”

Their first release, a red wine barrel-rested vodka, features a unique pink hue. But, don’t be fooled by the color—this isn’t a rosé, and it’s not sweet whatsoever. Instead, the spirit has hints of grape tannin and oak, and brings a solid splash of color and flavor to a vodka cocktail—but drinks well neat, too. Each barrel yields 200 bottles of product, and the team buys four barrels at a time. That means limited batches for each release, adding to the exclusivity of each bottle they produce.

While barrel-aging gives Crooked Oak’s line unique flavor, it isn’t the only thing special about these sprits. The Mamarys do everything on site—ferment, distill, age, and bottle. Licensed as a “farmer distillery,” they use locally grown products whenever possible. And, as a small, family-owned operation competing with giant distilleries at home and abroad, they’re doing more than just putting the product on a shelf for curious consumers—they’re giving you the opportunity to try it yourself.

Melissa’s days are spent bringing the product on the road, touring local liquor stores and restaurants for tastings, and to converse with customers one on one. “At tastings, so many people tell me, ‘I don’t like gin,’” she said. “But, I encourage them to taste it anyway. And, the reactions have been great, even from those who were hesitant at first.”

For naysayers, Melissa brings lemon and rosemary to add a zesty, fragrant twist to a standard gin and tonic. And, it works. “It helps bring forward citrus taste, rather than being just juniper-forward,” she said. “People love it.”

But, tonic isn’t required for Crooked Oak’s gin or vodka to carry their weight; it’s a stellar drink to enjoy neat, a change from how drinkers normally approach the spirit. “Gin is called a sauce; you don’t eat tomato sauce without pasta, so you don’t drink gin without a mixer,” said James. “But, Crooked Oak is good on its own.”

As they prepare to open the tasting room this spring (it’s open by appointment only for now), the Mamarys continue to spread the word about their gin, and search for new, unique flavors to bring to their drinkers, especially those who have previously sworn off the spirit.

“Our gin is a true example of a craft spirit, with simple ingredients and a complex flavor profile,” said Melissa. That profile is echoed in their name, Crooked Oak. Oak is the base of the barrels where spirits are aged, and the barrels come from around the world, leading to the idea of a very crooked, but delicious, end result.

“It’s all a little crooked, you know? How we got here, how we source the barrels, how we make our product. It’s off the beaten path. Just like our gin.”

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Tagged Family Entrepreneurship, Food Entrepreneurship, Startups, Entrepreneurship of All Kinds

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