Pleasant House’s New Location Is… Nowhere Near You (It’s Three Oaks, Michigan)

The second Pleasant House Bakery location in Three Oaks, Michigan.
The second Pleasant House Bakery location in Three Oaks, Michigan. Photo: Rupert Vaughan, courtesy Pleasant House Bakery

Bridgeport’s beloved English pie shop Pleasant House Bakery has a new location coming, and it’s in Three Oaks, Michigan, one of the small communities just on the other side of the Michigan-Indiana border that is popular as a summer cottage/getaway kind of place for Chicagoans. Penny Pollack announced it on Twitter over the weekend, and we spoke last night with Art Jackson, owner with his wife Chelsea of Pleasant House Bakery. “We got presented an opportunity in Michigan, and we said, Michigan, that’s crazy. So two days later we did it. We have a whole building.” We asked him to back up and tell us how it all came about, and here’s the story.

A friend of Art’s owns the building in Three Oaks, previously a winery and bar, and when Art was visiting him, he showed him the building and, just as importantly, introduced him to the thriving artisan food community in the area, which ranges from farmers who sell at the farmer’s markets in Chicago to producers like Local in New Buffalo (already a customer of his premade boxed pies) and the old school Drier’s Meat Market, to Journeyman Distillery and Greenbush Brewing Co.

The latter was particularly influential, since Art says “we’re a BYO restaurant, and I’ve seen so many people come with Greenbush growlers. It’s a neat little town, and it just felt so right, the timing was so right,” he says. For him, the area “is like Chicago’s wine country, like the Hamptons.” Art, who grew up in a small town west of Chicago, wasn’t really familiar with the area other than a few trips to the Indiana Dunes as a kid, but he remembers customers coming in who wanted to buy pies for taking back to Michigan “and I’m saying, let me get you set up with ice and pack them up for you and they’re like, Art, it’s an hour from the south side.”

The 100-year-old building, at 9 North Elm in Three Oaks, is set up as much more of a traditional restaurant than the modest Pleasant House Bakery in Bridgeport, and Art says “Our idea is to do what we do— pies being the main thing. Unique but good food, moderately priced. It’s much more formal than we have here.” He says the community there has been welcoming— they’ve already been invited to be part of an event at Journeyman Distillery on July 6, and he says when he stopped into a local tavern and grill, Nelson’s, the woman who runs it said “You’re the pie guy! I’m so glad you’re not doing the same menu we’re doing” with hamburgers and the like.

He’s not sure what their hours will be like year-round— as he says, there’s a seasonal attitude in a place like Three Oaks “which goes from sleepy little town in the winter to hustling summer town.” When will it be open? “As fast as we can move,” he says; the goal is to be open around Memorial Day, though all that depends on the local inspection and licensing process… which he’s currently studying up on as quickly as he can.

Pleasant House’s New Location Is… Nowhere Near You (It’s Three Oaks, Michigan)