Everyone who travels regularly on Route 32 from Kingston to Rosendale and New Paltz knows the infamous six-way junction where the state highway reasserts itself to become the southbound road known simply as Boulevard, after a vague meander through Midtown. It’s the spot where Fair Street ends, where Wall Street dwindles to South Wall en route to Wilbur, and where Greenkill Avenue gets ready to unload westbound traffic onto Washington Street a block away. It’s that headscratcher of an intersection where no motorist is ever quite sure whose turn it is to venture forward next. You know the one.
The road-meeting in question is dominated by a Stewart’s Shop; across Greenkill is King’s Pizza, and to the east is Boulevard Wine & Spirits.
The rest of this little mixed-use neighborhood hub has been going through a bit of a gentrification glow-up in the past couple of years, with the Green Kill performance space rocking out a few doors north and a new distillery called Wiltwyck Spirits is moving into the neighborhood. A former auto body painting shop at the top of South Wall is currently being converted into a cannabis dispensary called Lucky Green Ladies.
But the most striking structure at the intersection has long been a former Gulf Oil station, built circa 1920 in classic Art Deco style, sided with porcelainized steel enamel panels and festooned with glass blocks. The gas station closed in the 1970s and the building at 8 Fair Street lay dormant until 1998, when Bodacious Bagels of Stone Ridge took over and did a major cleanup and retrofit.
Meanwhile, a Culinary Institute of America graduate named Walter Swarthout had purchased the 30+-year- old Cake Box bakery on Route 28 in Woodstock. By 2001, the bagelry had decided to close its satellite store, and Swarthout took over the premises. He ran the Cake Box in its Kingston location until this past March, when he was ready to retire.
When HV1 paid a visit last weekend, the Cake Box sign was still up, but temporary signage announced the new business about to open there: Pinkerton’s Bakery. Its website promises a “focus on nostalgic desserts, pastries, sweet/savory pies and a small offering of breakfast and lunch items.” Renovations are proceeding apace, and a soft opening is planned for the first week in December. But you can already order special Thanksgiving pies for pickup, through this Sunday, November 24.
The last time new owner Angela Pinkerton was making Thanksgiving pies, at her previous business in Berkeley, California, her staff of five bakers had to produce 1,500 of them within a matter of days – up from 550 three years earlier. She had started Pie Society during the early months of the COVID pandemic “because I was bored,” she says, “and I thought it would be a comfort to the community.” Not only did Bay Area residents take her comfort food to their collective hearts, but they made Pie Society wildly trendy during its brief run, and local periodicals lamented the closure of the storefront in April 2023. “Yeah, I became a thing,” Pinkerton says with a self-deprecating laugh.
She came by her reputation honestly, however. An Ohio native, Pinkerton took a job in a bakery while studying Biology at Kent State University and “fell in love with baking,” in her words. She began making and decorating custom wedding cakes as a hobby and continued working in bakeries until she decided to formalize her training in pastrymaking at L’Academie de Cuisine in Gaithersburg, Maryland. From there she found work at the Ritz-Carlton Hotel in Washington, DC.
In 2007, as “a single woman who needed health insurance,” she decided to relocate to New York City after attending a culinary conference there and being intrigued by a cooking demo offered by a pastry chef from the restaurant 11 Madison Park. She found a gig as a pastry cook there through Craigslist, moved to a remote corner of Brooklyn and began working her way up to pastry sous chef, pastry chef and finally executive pastry chef over an eight-year period. She was one of a staff of 15 pastrymakers in a fine dining establishment with “60 people in the kitchen,” serving elaborate meals of up to 20 courses. During her time there, 11 Madison Park earned three Michelin stars and four stars from The New York Times.
By 2014 Pinkerton decided that she “wanted to do something else” and moved to San Francisco. “I was inspired by the bakery culture there,” she says. First, she worked as a consultant, helping a “very modern bakery” called Craftsman & Wolves expand its operation. With a friend who had escaped 11 Madison Park around the same time, she then founded a restaurant, pizzeria and wine bar group called Che Fico. “I learned to bake in a wood-fired oven. That was fun.”
After four years, she left the group with the intent to open a confectionary and chocolate shop, only to have the pandemic strike. Using a shared commissary kitchen and inspired by nostalgia for the pies baked by her grandmother, who had owned an orchard, she began taking orders, and Pie Society was born. The business was wildly successful and soon had its own storefront, but by 2023, she was ready to move back East to be closer to friends and family.
Having discovered the Catskills on weekend trips with her Westchester-based best friend while she lived in New York City, she decided on the Hudson Valley as her next destination. She and her partner Nate Pisa and their pitbull Cheeto found a place to live outside of Rhinebeck and started doing pop-ups out of the kitchen of the former Dixon Roadside near Woodstock, while looking for a store of their own. They found the Cake Box in January 2024. “Kingston is a cool place with a lot of culture,” Pinkerton says. “I came from a town similar to Kingston, sizewise, in Ohio.”
With Pisa spearheading the renovation, the new space has gradually been taking shape. They have upgraded the plumbing and electrical systems, ground and polished the painted concrete floor in the kitchen area, which was once a car wash. Some of the kitchen equipment – a walk-in refrigerator and freezer, a big rotating-rack oven – dates back to the bagel bakery. New equipment has been added as well: a couple of electric ovens, a proof box, an especially tall dishwasher that can handle sheet trays, a mixer and sheeter. “We’re doing some R&D and getting used to the machines,” Pinkerton notes.
In the more public central part of the shop, they have removed a half-wall to create a shared workspace where customers will be able to watch pastrymakers shape pies for baking while they wait to place their orders. “A lot of pastry kitchens are tucked away in a corner,” Pinkerton explains. “Part of my desire was to bring us out to work together – to function as a team, visually and physically.”
The east end of the building will remain the dining room, with tables for 14 people. Sun pours in through the tall south-facing windows and glass-block walls; adding a layer of ultraviolet-blocking film on the windows is one of the jobs remaining to be done to complete the renovation. Soon it will be a pleasant place to stop for lunch, as well as to bring home an artisan pie.
While some of Pinkerton’s specialty pies are old-fashioned family recipes, others are more modern, reflecting her background in high-end dining establishments. Her Passion Fruit Meringue Pie, for example, is “more like a plated dessert in a pie shell,” topped with bayleaf-infused sweet cream. Her Bourbon Chocolate Walnut Pecan Pie takes traditional pecan pie to an entirely new level. Her apple pie incorporates cranberries under an oatmeal streusel topping. Her pumpkin pie uses fresh roasted squash, not canned pumpkin. Scallion Biscuit Topped Turkey Pot Pie and tiramisu are also currently available, and a couple of the pies come in gluten-free versions.
Says Pinkerton, “The flavors for me have to really pop. They’re never cloying-sweet.” For glimpses of what gorgeous works of art these pies are, check out Pie Society’s old Facebook feed at www.facebook.com/PIESOCIETYHQ. Visit www.pinkertonsbakery.com for more information and to place orders for Thanksgiving pies.
Join the family! 
