The Owners of Sugarpine Drive-In Have Purchased the Former Shirley’s Tippy Canoe Property

More than a year after beloved restaurant Shirley’s Tippy Canoe was ravaged by fire, the Troutdale property—which over the decades had become a Gorge landmark in its own right—will be revived after all.

The husband-and-wife team who opened Sugarpine Drive-In in 2018 on the banks of the Sandy River about 2 miles to the north closed on the 1.5-acre site earlier this month, as first reported by The Oregonian. Emily Cafazzo and Ryan Domingo plan to bring the restaurant back to its 1930s roadhouse roots following a ground-up rebuild that will include indoor and outdoor seating. Rehabilitating the business is part of the couple’s overall goal to reestablish the Historic Columbia River Highway as a culinary destination.

“In the original days of the Historic Highway, there used to be dozens of roadside pit stops, eateries, and confectionaries selling things like homemade ice cream, roasted and fried chickens, and fried fish sourced directly from the Sandy River,” Sugarpine chef and co-owner Ryan Domingo said in a press release. “One-hundred years later, we’re excited and incredibly honored at the opportunity to both celebrate the unique beauty, and build upon the culinary heritage of this small corner of the Pacific Northwest.”

Cafazzo and Domingo have tapped award-winning Waechter Architecture to orchestrate the new structure’s design. The firm is best known for its modern, streamlined looks at venues as varied as the Society Hotel Bingen to the Blu Dot Showroom, a high-end furniture store in the Pearl.

Though Sugarpine Roadhouse is currently scheduled to open in the summer 2022, you won’t have to wait that long for the duo to launch another culinary project. Starting Thursday, April 22, a pop-up food truck named Da Pine will begin serving customers at Glenn Otto Park, which is adjacent to the original Drive-In.

The mobile kitchen is designed to operate as something of a recipe incubator, so you can expect to see multiple types of cuisine coming out of the window that will eventually be prepared by other staff members. First up is Da Pine Grinds, or Hawaiian-style takes on Sugarpine’s designed-for-Insta-clicks fare. The menu is designed by resident grill master Darrin Domingo, chef Ryan’s brother, whose plate lunches, flavorful poke bowls and slushies are inspired by his family’s roots on the island of Kauai.

Sugarpine’s co-owners say that the expansions are a sign that the business has managed to defy the odds and prosper during the pandemic. The refurbished 1920s gas station continued to serve a record number of guests throughout the past year.

“We’re one of the lucky few who’ve been able to weather the storm and come out alright,” says chef and co-owner Emily Cafazzo. “The very nature of our business—the type of food, the service style, our location—made the impossible situation created by the pandemic somewhat manageable. If anything, the pandemic magnified some of the most essential benefits of the product and service we offer our customers: the chance to leisurely escape the city or the suburbs, take in some of the natural beauty of the Historic Highway, and share a positive, nostalgic experience with the people in your bubble.”