After a summer largely spent welcoming new restaurants and gearing up for further openings, September concluded with the news that several beloved spots wouldn’t make it to 2027, including wine bar OK Omens—marking the end of the nearly 30-year legacy started by Castagna. Still, we also have a few places to look forward to, including a day-to-night cafe-meets-bar serving up Brazilian snacks. Read on for the roundup.

Say Goodbye To: 

OK Omens

OK Omens’ Dungeness crab salad and mackerel crudo. Photo by Josh Chang

It’s hard to think of a name more synonymous with the Portland restaurant industry than Monique Siu, even if many locals won’t immediately recognize it. The venerated restaurateur co-opened the famed Zefiro in 1990, helping usher in the early days of Portland’s culinary emergence. In 1999, she opened Castagna on SE Hawthorne with chef Kevin Gibson, then followed it up with the more casual counterpart Cafe Castagna. With chefs like Matthew Lightner, Olympia Provisions’ Elias Cairo, and the late Justin Woodward, Castagna grew to be one of Portland’s most celebrated restaurants, and its influence spread throughout the city.

In 2018, Siu, Woodward, and sommelier Brent Braun restructured (and remodeled) Cafe Castagna as the wine-focused bistro OK Omens, with a nearly obsessive focus on riesling and fun tasting notes. Castagna closed in 2020 due to the pandemic and officially shut its doors in 2023, but OK Omens continued to evolve. Woodward departed in 2024, and up-and-coming chef Joseph Papas stepped in the following year. Papas refocused on a minimalist menu driven by seasonal vegetables and Pacific Northwest seafood, including a spectacular Dungeness crab endive salad, plus one of the best $1 oyster happy hours in the city. But at 74, Siu’s next move is understandable: retirement. After decades shaping the city’s tastes, Siu will close her final restaurant on Saturday, October 17.   

Oven and Shaker

For the last 15 years, Oven and Shaker has been a staple of Pearl District dining. Chef Cathy Whims—founder of the legendary Italian restaurant Nostrana and six-time James Beard Awards finalist—teamed up with star bartender Ryan Magarian to open the pizzeria and bar in 2011. It wowed diners with its wood fired oven pizzas, melding traditional Italian flavors with Pacific Northwest elements, like its ultra-porcine Maple Pig and the goat cheese pizza with pistachio pesto. Magarian’s Pepper Smash #2, an aquavit cocktail with bell pepper and maple, became an instant Portland classic. Sadly, on September 22, Magarian posted on Instagram that Oven & Shaker’s last day would be October 30, and expressed his gratitude for the last decade and a half of service. 

Bistecca

Bistecca’s namesake bistecca alla fiorentina. Courtesy of Bistecca

2025 saw a tsunami of new Italian restaurants crashing into Portland, and one of the earliest in that red sauce wave was Bistecca in Slabtown. At the beginning of the year, chef Gabriel Pascuzzi, a Portland native and Top Chef contestant, closed his roast chicken restaurant Mama Bird and reopened it as an Italian-inspired steakhouse. Bistecca distinguished itself from other Italian spots with its bold menu, including fried arancini, a massive oxtail-topped burger, and the eponymous Bistecca alla Fiorentina. Early reviews were mixed, but Bistecca started building steam as it progressed. Late in 2025, Pascuzzi closed his adjacent fast-casual spots Tip Top Burger and Feel Good, reopening the shared space as Hey Luigi, a companion bar to Bistecca focused on pastas and cocktails. But, as he told the Oregonian, the Trump administration’s tariffs, rising gas prices, and other economic struggles are forcing him to close the business on October 17. Thankfully, he’ll be keeping things going at Hey Luigi.  

Say Hello To:

Modhaus

Part of Modhaus’s interior, taking inspiration from mid-century design. Photo by Gregor Halenda

As we’ve covered previously, these last few months have been the summer of food cart pods. Modhaus technically opened much earlier in the year, but the roll-out has been gradual, with food carts slowly joining the space. On Friday, September 18, Modhaus’ sprawling new indoor space officially opened, with 100 indoor seats, a full bar and café, and sleek mid-century design. An covered outdoor seating area, still awaiting finishing touches, will offer two fire pits, heaters, and 100 additional seats. The carts include fried chicken sensation Jojo, Filipino-American fast food-inspired joint Makulit, and Thai spot Chick & Pig, which moved from the Woodstock neighborhood to join the fun. The most recent addition: Tidal Boar’s Shuck Truck. Formerly stationed at Level Beer’s Northeast location, it’s likely Portland’s only dedicated oyster food truck. Modhaus is open at SE 38th and Division, seven days a week. 

Look Forward To:

Bossa

At one time, Portland had its fair share of coffee shops that transitioned into a bar in the evening, but most died off in the pandemic years. Bossa, from husband and wife Emanuelle and Tilion Lieberman, looks to bring back those vibes—with Brazilian flair. The pair have been hosting pop-ups at Sunblossom Farm in the Cully neighborhood, and will open Bossa as a brick and mortar on NW 21st, presumably in October. Visitors can expect Brazilian coffee and espresso drinks, plus tapioca crepes and pão de queijo—Brazilian cheese bread—during the day. In the evenings, find bar food and cocktails, including Brazil’s signature drink, the caipirinha. Also look forward to DJ dance parties and the possibility of truly late hours, like 2:30 am on weekends. 

Pronto Gelato

Pronto Gelato, a collaboration between the owners of Italian restaurant Campana and Italian coffee roaster Spella, will serve gelato, coffee, and pastries. Photo by Jenny Kang Photography

For over a decade, Staccato Gelato served its creamy desserts along with donuts and coffee on “Restaurant Row,” that strip of 28th crossing East Burnside. While it quietly closed months ago, gelato fans won’t have to wait long for its replacement. Pronto Gelato—from the team behind Woodlawn’s Italian restaurant Campana and Italian coffee shop Spella Caffè—is moving into the space by (hopefully) late October. 

Currently, you can find Pronto Gelato at Woodlawn Italian restaurant Campana, at Pronto Gelato’s seasonal scoop shop on 42nd and Alberta (which is currently closed for the season), and numerous shops and restaurants around town. But this new location will be its first permanent, standalone business, serving more than just gelato. Co-founder George Kaden of Campana says they’ve partnered with Michelle Vernier of Bella’s Italian Bakery in Lents and plan on opening at 8 am daily with Spella Coffee drinks, pastries, and breakfast sandwiches. The shop will remain open until 10 pm for gelato and other desserts that are still being dialed in, though Kaden says there will be cookies and probably tiramisu and cannoli. At open, Pronto Gelato will operate as a scoop shop, but the team plans on adding cold cases for retail gelato and, potentially, a bar. “If the neighborhood wants an aperitivo hour, we’re going to have that,” he says, but cautions that it won’t be for weeks, if not months, after opening.