Pie in the Sky: The Vineyard’s best local restaurant

This gem is a beacon reminding Islanders they’re almost home.

Nothing better after a long journey than the full bakery at Pie in the Sky. —Tina Miller

At first, the title for this article was a joke. But the more we thought about it, the more it rang true. THE local restaurant that serves ALL (or maybe most) Martha’s Vineyard residents is, in fact, off-Island.

For many a Vineyarder heading off-Island, Pie in the Sky is our first stop. For breakfast, lunch, a road snack. For any Vineyarder heading home, Pie in the Sky is a beacon. The light at the end of the road, signaling that journey back to the Island is now just a boat ride away. Before the Steamship engines rattle and the horns blow, we stop, get our tea, a popover, a cookie to hold in our hands to hold us over as we make the crossing.

Pie in the Sky has been “baking in the Hole” since 1982 when a young couple, Manny and Denise Dias, were on their honeymoon in Europe and noticed that every town had a local bakery and coffee shop. It wasn’t too much of a stretch for Manny to be thinking about opening a bakery. His parents owned Jean’s Bakery in Teaticket, Mass. Upon their return, Manny and Denise began looking for a location. They soon learned there was a kite shop run by local artist Joan Kanwisher that might be available. They leased the shop the following year and sold Kanwisher’s prints. According to an interview with the Woods Hole Museum, “They were trying to think of names for the shop and not getting anywhere until one day Mr. Dias had the radio blasting the Jimmy Cliff song, ‘The Harder They Come’… ‘Well they tell me of a pie up in the sky…’ “It was the perfect name, and it still remains.”

General manager Erik Gura greets Edible on a gray fall morning. Dressed in green Carhartts, Crocs, a black vest, and a cap, carrying a yellow ceramic coffee mug, he blends in with the 10 or so other men wearing essentially the same Woods Hole uniform. Erik Gura bought Pie in the Sky from the Diases in 2002. Eight years earlier, he had arrived in Woods Hole to work as a ship’s steward for the SEA education program. “I loved it, but I wanted to have kids and wanted to be around to raise them,” Erik says. With kids, he has realized this goal. His wife, Megan Essex, and children, Frank, age 9, and Noah, age 7, are a part of his daily life — and the business. “They break down boxes, help me stock the shelves. We live just up the street, so if I need to run down here and check on something, they can come with me,” Erik says.

Erik professes a lifelong love of food. “I have been working in restaurants since I was 12, growing up in Newburyport. Washing dishes, busing tables.” While in college at UMass Amherst, he and a friend started a catering company. “I’m completely self taught. We served homemade, good quality food, cooking for university staff. That kind of a thing.”

Pie in the Sky’s former owner and current general manager Erik Gura. —Tina Miller

Erik’s purchase of Pie in the Sky was a leap. “I risked everything to start this business,” he says. “Working on a boat prepared me in some ways for this business. The small space, efficiency, people around all the time. This place is going 24/7. At midnight we begin baking the pastries. At six we begin baking our breads — wheat, sourdough, rye. Then we roll into making the cookies, pies, bars, and quiches. It is a constant flow. There are always three or four people here. It is a puzzle of food, people, and time. It is almost like producing a theatrical production.”

In the summer, Erik has 70 employees to support the nonstop food and drinks to support the flow of summer and Steamship traffic. He estimates that about 80 percent of his customers are from ferry traffic and says, “It takes us a week in January to make what we make in a day in July. When you look at the books, it is like a beautiful sine wave.”

As he shows Edible around the “new, improved” 2017 Pie in the Sky renovation, Erik points out the radiant heated sidewalk so he and his staff don’t have to shovel the entire patio by hand — and there is no danger of ice for older customers. He shows us the spectacular view from the cafe’s roof, which has a live camera feed for those who want to tune in and see what is happening in the harbor. And he walks us into the basement where one realizes that the entire upstairs/outside patio area is sitting over a giant refrigerator and freezer that, at -9 degrees, is “painfully cold.”

“We used to have about 11 refrigerators down here. One was always breaking or leaking. Having this new refrigeration setup has been a game changer,” Erik says. And, even though Pie in the Sky is relatively newly renovated, the maintenance is “as intensive as a boat. Constant cleaning, repairs, upkeep.”

“We have about 400 items to source from three dozen vendors,” Erik says. “I source local ingredients as much as I can. We make our own bread, roast our own meat. I want every person to be able to walk in the door and find something that appeals to them. Beyond the boat traffic, this is a crossroads. You have the MBL, WHOI, SEA education program, U.S. Fisheries, NOAA, the bike path. Best people-watching on the planet.”

Customers can catch a glimpse of the kitchen beyond the full cases of pastries and menu boards. They’ll find baker Kendall Stouffer working on a bench, laminating dough for croissants. “We use about 15 percent whole wheat flour in our croissants,” Erik says. And head baker Tiara Ruggeri is ferrying freshly baked chocolate croissants to the pastry case out front. Meanwhile, three people behind the counter take orders, make espresso drinks, and chat with the kitchen about new and upcoming orders. No one is shouting. No one seems stressed, but everyone is moving at a steady clip.

In the cafe, Pie in the Sky’s coffee roaster, Gray Eldridge, is pouring green beans into the roasting machine and sets a timer. Within seconds, the seating area becomes coffee-scented. Gray estimates that he roasts about 70,000 pounds of coffee a year. He sets a timer on his phone and grabs a cup of coffee while he waits for the roaster to do its thing.

Outside folks sit, eat, chat, or wait for their food. Across the street is “the wall,” which, according to Erik, is where many of the locals hang and drink their Pie coffee.

Back in Erik’s office, which is not much larger than a closet, one can find Pie in the Sky merch stacked up against one wall, a couch that could house a small sleeping child with a black canvas Pie in the Sky banner above it, a computer, and a desk filled with lots of tchotchkes. Scientist fans of Pie in the Sky have gifted Erik things like a mug featuring the invented species “Barchypopover Loebenis.”

In 2022, Erik sold the business to BT Brands Inc., a small publicly traded company. “But I am here for the duration,” he says. “I still own the building, the land, and am the general manager of the store. From the outside looking in, it’s the same. But thanks to BT Brands, I now have the resources to invest in new equipment and offer better wages. It has increased Pie’s staying power in the community. And now we can do things like be open from 6 am to 9 pm.” Erik leans back in his chair and sighs. “Of course there are easier ways to make money, but I love the people, the cooking, the science. I love the whole thing.”