At the tip of Aquinnah, sitting just below the majestic Gay Head Lighthouse, is an up-Island destination that has only become more beloved over time, the Outermost Inn. In a genuinely provincial community with six towns, many of us are hunkered down in our neighborhoods and consider a drive to Aquinnah a true trek. Yet folks will drive to the far western end of the Island for beautiful food, strikingly dramatic surroundings where deer casually stroll by and ospreys fly above at the edge of where the ocean meets the land. Besides the beauty of the natural surroundings, the real reason guests keep coming back is the Taylor family tradition and hospitality they find at the Outermost Inn.
Hugh and Jeanne Taylor built their home in Gay Head in 1971, and in 1998 the town officially changed its name to the original Wampanoag name, Aquinnah. By the mid-70s, the Taylors started a family, and their daughter Alexandra (Alex or A.T., named after Hugh’s older brother Alex Taylor) was born. Two and half years later, Isaac Taylor arrived.
“We used to rent the house in the summer to pay bills,” Hugh said. “By the late 1980s, the house needed repairs and upgrades, and so we decided to create the inn.” Hugh and Jeanne thought they also needed to diversify their income sources a bit.
“We went to the bank with a proposal and a prospectus to justify them lending us money to convert our home into a B&B, and they fell for it,” Hugh says. “We used that money to convert the house, adding seven guest rooms.”
Hugh figures it was around 1991 when they finally got the permit to open the restaurant to the public. “It’s grown exponentially over the years,” Hugh adds.
Growing up in the family business, Alex and Isaac helped their parents run the seasonal inn and restaurant, doing everything from washing dishes to landscaping.
“As a teenager, I would work around the inn during the days, then I decided to try something different and started working at the Home Port at night. I did that for a few years,” Alex explains.
“With the inn and restaurant opened to the public, it was busy. Eventually I transitioned from working at the Home Port to working here.”
Isaac had his own interests, though not far from home. He now lives across the street with his wife, Noli Taylor, and two teenage kids. Isaac and the kids are always around to help out.
As an adult, Alex also worked full-time in administration at the Martha’s Vineyard Charter School. After twenty years at the Charter School, marriage, and twin daughters Olive and Violet, it was time for a change.
“I was doing both, the Charter School and this, and in the end, I couldn’t do both 100 percent. Both jobs got 50 percent of my time, and both were suffering,” Alex says. “And so I either had to give up this or give up that. At that point, I wasn’t ready to give this up. They [Hugh and Jeanne] weren’t ready either. They certainly didn’t want to take on more responsibility if I transitioned out.”
Hugh explains how he felt about Alex coming on full-time.
“We’re not restaurateurs,” he says, “basically, we’re entertainers, and Alex has come to the table with the knowledge totally in hand. So we wanted her in, but we really weren’t sure whether the place could afford it.”
Around this time, Covid hit, and like many in the restaurant and hospitality business, they had to pivot or perish. Hugh says he and Jeanne would always tweak things every few years to keep customers interested, and this became a time to re-invent once again. They needed to get creative with their business model, which had become exhausting for Hugh and Jeanne after so many years. “Jeannie and I were beginning to wilt a little bit from that, you know, the six months 24-hours-a-day,” Hugh says.
With the pandemic, renting rooms to the public was no longer feasible. Also, the housing crisis began to become critical. When it was time to reopen after Covid, the Taylors realized they were sitting on gold and could now house their kitchen staff and put all their focus on the restaurant.
Alex was running the front of the house, with energy, vision, and focus — with her feet firmly planted in the family business. A fresh breeze lifted the Outermost into a new era.
Covid caused a major shift, but it was a positive one for the business. Suddenly all of their outdoor seating became a major silver lining. This gave them a huge advantage, and suddenly a new set of diners were willing to take the dreamy scenic ride up the Island to the Outermost Inn, where they had plenty of parking, open space, and peaceful quiet. The restaurant hit its stride and became a sanctuary during the pandemic.
“We can open the place up to everybody. And so it gives them a feeling of what this Island is like, and what it has been like for all these years. We’re inviting people into our home,” Hugh says.
The food has always been exceptional, featuring a prix fixe, three-course menu for years with a menagerie of talented, excellent chefs. They keep the family vibe going and cook up beautiful meals served on tables with flowers grown on the property. They have always hired locals and Island kids to work at the restaurant.
“As a guest at these tables, you see people you know or maybe a high school kid, and the guest asks, ‘Hey, do you live here?’ And the young Islander says, ‘Oh, yeah, I grew up down the road, and spend my days fishing on the local waters off the Island,’” Alex explains. “It’s authentic and that’s important to us.”
Alex’s own daughters are no exception, now rising seniors in high school, you will find them working in the restaurant, keeping the family tradition alive.
This season, however, brings a new chef.
“We were blessed to have some incredible chefs here,” Alex says. “I mean, I don’t know how we tripped over all the great chefs over the years.”
This year was the first year the family conducted a professional search for a chef. Their last chef, Scott Grilli, came to them during Covid, another streak of good luck out of the pandemic.
“Scott was incredible, and we all learned so much from him,” Alex says. But, as life happens, Grilli is also in the middle of a sailing adventure around the world, and he needs to be free to keep going and not just sail in the winter.
After months of searching and 25 resumes, the Taylor family found Chef Bryan Johnson, who lived and worked in New Orleans. Johnson worked in restaurants including N7, Le Chat Noir, and Sofia. The Taylors traveled to New Orleans, a food paradise, last winter and Chef Bryan and his team cooked a beautiful meal for the Taylors.
“The experience was incredible,” Alex says. “They were incredibly well organized. I mean they really pulled it together for us in a way that was very, very impressive.”
The new chef was not only concerned about packing up and moving to the remote western end of Martha’s Vineyard, but also about pulling together a kitchen team and how to get supplies to the restaurant. In the end, Chef Bryan brought his team from New Orleans, including a master oyster shucker, for a seamless transition.
As for sourcing supplies, most people who eat locally assume restaurants have plenty to choose from, but most Island farmers are smaller scale and prefer not to wholesale everything they grow. The farmers need to keep their own farm stands stocked and are also committed to the Farmers Market, so it is difficult to fill an entire menu with local food. Ironically, the most difficult item to get in Aquinnah is fresh fish. It seems no one wants to deliver past Chilmark center. In the past, the crew at Outermost Inn have had great luck with the Fisherman’s Collaborative, an extension of the Martha’s Vineyard Fishermen’s Preservation Trust out of Menemsha. Still, the Outermost makes it work to include as many locally grown ingredients as possible, from oysters, clams, and lobster to fresh salad greens and vegetables. Johnson and his team came to the Island a month early to learn the lay of the land — and sea — and to learn the intricacies of doing business on an Island.
Every year is a new season on the Vineyard; it’s an opportunity for businesses to reboot, retool, and refresh. This is something the Taylor family has done well over the past 33 years, welcoming the public to their home and business. The family vibe, authenticity, quality, and familiar Island faces, is the secret sauce to the longevity of this family jewel.