Old Friend Pizza Moves Its Detroit-Style Squares From Pop-Ups to a 10-Seat West Roxbury Shop

Photo: Pi.1415926535, Wikimedia Commons, CC BY-SA 4.0. Washington Street in West Roxbury, the road where Old Friend Pizza opened (file photo, July 2021; not the shop).

Old Friend Pizza, a Detroit-style pizza business that built a following at pop-ups around Roslindale, now has its first permanent shop at 5272 Washington St. in West Roxbury. Universal Hub reported on Oct. 27 that the small, 10-seat space was opening that week, and the business’s own website now lists regular service there Wednesday through Sunday, 5 to 8 p.m.

From pop-up to storefront

Alden Caldwell started Old Friend as a roaming pop-up, cooking at events in Roslindale, at the Exodus Bagels Airstream and at The Substation, according to Universal Hub. The website says the business still holds a residency at The Substation, at 4228 Washington St. in Roslindale, usually Thursday through Saturday from 5:30 to 8 p.m., and still makes special appearances at the Roslindale farmers market. Boston.com spelled the chef-owner’s surname “Cadwell”; Universal Hub uses “Caldwell.”

Universal Hub reported that the Boston Licensing Board was to vote on a request to serve between noon and 9 p.m. daily, and that no hearing was needed because the address already held a licensed restaurant. The storefront’s most recent tenant was How’s Your Meat, and before that a series of restaurants, including Cristelle’s pizza and sub shop. The posted hours on Old Friend’s site are shorter than the licensed window, and the site warns that private events and sell-outs can change service, so it points customers to Instagram for same-day updates.

What makes the pizza Detroit-style

Detroit-style pizza is baked in a rectangular steel pan, with cheese pushed to the edges so it caramelizes into a crisp border. Old Friend’s site describes three-day fermented dough, a sauce built on Jersey tomatoes, and cheddar and mozzarella spread all the way to the edge of the pan, with four corner slices per pan. It says everything is made from scratch.

Boston.com described seasonal collaborations with local farms, including a pie with delicata squash from Heavens Harvest Farm in New Braintree, spruce tip maple syrup crème from Baird Farm and sage from the chef’s own garden. Regular options include a charred pepperoni and a cheese pizza, plus a chicken Caesar pizza that was a pop-up favorite. Boston magazine listed the West Roxbury storefront among November’s new locations of familiar restaurants and described the pies as slow-fermented, crisp-edged rectangles.

The Boston Report has not tasted the pizza; descriptions come from the business and the outlets cited. Menu prices were not shown on the official homepage when we checked.

A neighborhood pizza shop

Old Friend calls itself “your neighborhood pizza shop,” and the small dining room fits that pitch: with 10 seats, many orders are likely to be takeout. The shop is on the Washington Street corridor that runs from Roslindale toward Dedham. The West Roxbury and Highland stops on the Needham Line commuter rail are the closest train stations, though not walking-close for everyone.

The opening adds another square-pie option for Boston pizza fans outside downtown. For more neighborhood picks, see our guide to the best restaurants in Boston.

Sources

• Old Friend Pizza, official site: locations, hours and contact (checked Nov. 7, 2026)
• Universal Hub, “West Roxbury to get taste of Motown with new Detroit-style pizza place,” Oct. 27, 2026
• Boston.com, “5 restaurants we can’t wait to try in November,” Nov. 3, 2026
• Boston magazine, “Where to Eat in Greater Boston for November 2026,” Nov. 5, 2026