On Martha’s Vineyard, where businesses rise and fall with the rhythm of the seasons, maintaining a long-standing business is no small feat. Winters are quiet and lean, summers bring a rush of activity, and essential establishments must constantly balance the needs of a year-round community with the realities of a continuously fluctuating economy. Yet for nearly four decades, one small independent pharmacy on State Road in West Tisbury has remained a steady presence. Its story reveals something larger about the adaptability required to keep a small business alive on an Island where the seasons dictate everything.
Inside Conroy Apothecary, locals pick up prescriptions, buy a newspaper, browse gift items, grab a cup of coffee, or simply stop in to chat. In a place where familiarity and trust matter, the pharmacy has become part of the social fabric of the Island. At the center of it all is owner and pharmacist Tami Conroy Hersh, whose path back to Martha’s Vineyard began with a mix of practicality, passion for healthcare, and a willingness to take a risk.
Hersh graduated from Martha’s Vineyard Regional High School in 1980, and then left the Island for pharmaceutical studies at Northeastern University in Boston. “I’ve always loved chemistry, and I’ve always appreciated the importance of healthcare,” she notes.
After graduating in 1985, she remained in the Boston area for several years, working first at an independent pharmacy, and later at Walgreens. But the Walgreens experience left her feeling disconnected from the kind of work she had envisioned. “I really disliked the whole big-chain mentality,” she says.
At the time, the pharmacy industry was undergoing a major shift. Chain pharmacies were rapidly expanding across the country, squeezing out smaller independent operations. Many independent pharmacies were closing their doors entirely. It was an unlikely moment to consider opening one, but opportunity appeared back home on Martha’s Vineyard.
In 1988, a new commercial building — the Middletown Exchange — was being developed along State Road in West Tisbury. The owner envisioned the property as a small medical hub, and believed a pharmacy could serve as a central anchor for the complex. Hersh’s mother, Natalie Conroy, who worked in real estate on the Island, encouraged her to consider the possibility.
“Naively,” Hersh says with a laugh, “my husband and I moved back here, and essentially built the pharmacy from the ground up.” It was a bold decision at a time when independent pharmacies were disappearing nationwide. “We worked very hard,” she says. “It was a long road.” Today Conroy Apothecary is entering its 38th year in operation.
Longevity in the pharmacy world rarely comes by accident. As the healthcare and retail landscapes evolved, Hersh learned that survival required adaptability. One of the ways Conroy Apothecary has stayed relevant is by carving out a niche in community healthcare.
“We do a lot of vaccinations,” Hersh explains. “Making sure people are up-to-date on their immunizations has become a big part of what we do.”
The pharmacy’s immunization program has expanded significantly over the years, offering residents convenient access to vaccines without needing to leave the Island or wait for a doctor’s appointment. At the same time, Hersh has paid close attention to what her customers want from the retail side of the business. The store carries a mix of health products, beauty items, and thoughtfully chosen gifts, small touches that make the space feel welcoming rather than purely clinical. But perhaps the most important factor in the pharmacy’s success is something less tangible: reliability.
“We’re consistently open,” Hersh says. “Even during the pandemic, we never shut our doors.” In the blizzard, they were vital — and available — to those who needed to fill prescriptions. In a community where residents depend on consistent access to healthcare, that dependability matters. The business also stays open until 6 pm on weekdays, allowing easy access even for the 9-to-5 working crowd. This availability is even more important since the closing of the venerable Leslie’s Drugstore on Main Street in Vineyard Haven.
Over time, Conroy Apothecary has evolved into something more than a place to fill prescriptions and grab cosmetics. Early each morning, before the pharmacy counter officially opens, the front of the store quietly transforms into a gathering spot. Hersh’s husband, Stan, opens the doors and starts the coffee. A group of regulars drifts in, flipping through newspapers, sipping coffee, and discussing the Island’s latest — everything from town politics to local events. The pharmacy department remains closed until the pharmacist arrives, but the front store hums with conversation, and for many Island residents, that informal morning ritual has become part of their daily routine. As the weather warms up, they often congregate on the porch. It is a pharmacy for all seasons.
Another unexpected way the business has deepened its connection to the community is through a simple delivery service. Years ago, Conroy Apothecary operated a second location in Oak Bluffs. But maintaining two full pharmacy inventories proved difficult, especially during the winter months. Ultimately, Hersh and her husband made the difficult decision to close the Oak Bluffs store, but they didn’t want to abandon the customers who had relied on them there. Instead, Stan came up with a solution. “He decided he wanted to continue taking care of the people we had been serving,” Hersh says. So he began personally delivering prescriptions to those Oak Bluffs customers, especially elderly residents who had difficulty traveling across the Island. Today, Stan regularly delivers medications to assisted-living facilities and those with mobility issues throughout Martha’s Vineyard.
“For many of them,” Hersh says, “he may be the only person they see all week.” The visits have become moments of connection: a brief conversation at the door, a familiar face stopping by. Many customers now rely on the service, and their loyalty to the pharmacy reflects that personal attention.
Running a year-round business on Martha’s Vineyard comes with a unique set of financial challenges. For Hersh, managing the rhythm of the Island economy has become second nature. “The winter months are incredibly lean,” she says. With fewer residents and minimal tourism, sales drop significantly. Meanwhile, summer brings a dramatic surge in customers who depend on Conroy’s too. Managing those extremes requires careful planning. “You have to be really smart about inventory, salaries, and cash flow,” Hersh explains.
In the spring, she begins gradually increasing the store’s inventory, preparing for the busy months ahead. “You need to have the products people want when they arrive,” she says. But stocking shelves too early can strain finances during the quieter months: “It’s a real balancing act.”
The front of the store plays a key role during the summer season. While prescriptions provide steady year-round business from Island residents, the gift items and retail products become especially important when visitors arrive. “It’s what helps sustain the pharmacy side of things,” Hersh says.
Over the past four decades, Hersh has watched the Island and the retail world evolve dramatically. Online shopping has changed consumer behavior everywhere, and Martha’s Vineyard is no exception. That shift has made community loyalty more important than ever. “You just have to give customers what they want and make them happy,” she says. “So they’re loyal to you, and don’t just jump on Amazon.”
For Hersh, maintaining that loyalty means staying accessible, reliable, and personal in a way large corporations cannot replicate. Her approach reflects the spirit of traditional small-town pharmacies, where pharmacists know their customers by name.
When asked what advice she would offer a young Islander hoping to start a business on Martha’s Vineyard, Hersh doesn’t sugarcoat the reality. “You need to have a cash reserve,” she says. Seasonal fluctuations mean new businesses often face months of minimal income. “You really need backing during those winter months,” she explains. “There’s just no way around that.” Vineyard entrepreneurs must learn to budget for the entire year, not just the busy summer. It’s practical advice from someone who has navigated that cycle for decades.
Looking back, Hersh admits she didn’t initially think of opening a pharmacy as a community mission. “When we first opened, it was really more about wanting to do what I love and support my family,” she says. But over time, the role of the business evolved.
Today, Conroy Apothecary is a place where residents gather, neighbors check in on one another, and essential healthcare services remain close to home. “I think we’re really a pillar of the community,” Hersh says. It’s a quiet kind of success, built not on expansion or scale but on consistency, service, and trust.
Nearly four decades after that leap of faith in 1988, Conroy Apothecary continues to serve the Island in the same way it always has, by showing up day after day. And on Martha’s Vineyard, that kind of year-round dependability is something that should never be taken for granted.