Boston/ Food & Drinks

West Roxbury Welcomes Old Friend Pizza, a Detroit-Style Square Pie With a Pop-Up Past

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Published on October 29, 2026
West Roxbury Welcomes Old Friend Pizza, a Detroit-Style Square Pie With a Pop-Up PastSource: Google Street View

Old Friend Pizza is opening this week at 5272 Washington St. in West Roxbury, bringing its Detroit-style square pizza to a permanent home after years of popping up around Roslindale. The dough gets a three-day ferment before it ever touches a pan, and the business is known for a crown of cheddar and mozzarella baked edge-to-edge against the steel.

The move marks the first brick-and-mortar location for a business that started as a roaming pop-up, according to Universal Hub. Old Friend Pizza is behind Alden Caldwell, whose cooking has shown up at popups in Roslindale, at Exodus Bagels and at The Substation, per the same report. The business had requested service hours of noon to 9 p.m. daily in the new space, which seats just ten people.

From a Bagel Airstream to a Permanent Pan

Before settling into West Roxbury, Old Friend Pizza built its following the hard way, working out of the Exodus Bagels Airstream, setting up at The Substation, and serving squares at the Roslindale Farmers Market, according to Boston Restaurant Talk. The business's own site confirms that trajectory, noting that it started as a roaming pop-up and now has a residency at The Substation alongside its first permanent location in West Roxbury, per Old Friend Pizza's website.

That residency has already put plenty of squares in front of hungry Roslindale regulars. The Substation has advertised nights featuring Detroit-style pan pizza from Old Friend Pizza alongside drinks from its bar, according to the venue's own events listing. The pizzeria also took over the kitchen at the Square Root in Boston for a one-night menu takeover built around scratch-made corner slices this past April, per an event listing on ma.to.

What's on the Menu

The signature formula, per Old Friend Pizza's website, centers on three-day fermented dough, Jersey tomato sauce, and cheddar and mozzarella stretched all the way to the edge of the pan. The online ordering page, which lists the shop's address as 5272 Washington Street in Boston's 02132 ZIP code, shows a menu that goes well beyond a basic cheese pie.

There's a vegan option built on tomato sauce, vegetables and a garlic swizzle with no dairy, according to the restaurant's ordering page on Toast. A chicken pizza comes topped with romaine and housemade Caesar dressing, while a more adventurous pie features oxtail cooked for five hours, shredded and finished with jalapeños and red onion, per the same listing.

Part of a Bigger Square-Pizza Wave

West Roxbury's new arrival lands in the middle of a broader Detroit-style pizza boom that has been building across Greater Boston for nearly a decade. The style first started making headway into Massachusetts in 2017, according to Eater Boston, pointing to Volo Craft Pizza's fall 2017 opening in Swampscott as a turning point that helped the format reach a wider local audience. Otto also began testing Detroit-style pies through pop-ups that same year before adding them to menus at some of its Maine and Massachusetts locations, the outlet reported.

The trend kept building from there. Somerville's Avenue Kitchen & Bar started offering Detroit-style pizza in 2019, and the format really caught fire in 2020 as people stuck at home went looking for comforting takeout, Eater Boston noted. Natick's Square Mfg. Co. opened at the end of that year riding the same wave. More recently, Detroit Pizza Co. opened as a takeout- and delivery-only spot at 600 A Washington St. in Brighton's Oak Square neighborhood, according to Boston.com, which described the Detroit-style trend as one that has spread across the country and is still expanding locally.

Old Friend Pizza's jump from pop-up circuit to a storefront of its own fits that pattern, giving West Roxbury a dedicated outpost for a style that's been building momentum in pockets of the region for years. Readers curious about the rotating specialty pies and the shop's pop-up roots can find more on Old Friend Pizza's website or follow along on Instagram.