20 Years of Fine Dining: The Painted Lady Marks a Major Milestone in Newberg

NEWBERG, Ore. — A 20-year anniversary for a restaurant is almost always cause for celebration. And for good reason: according to the Bureau of Labor Statistics, only 51.4% of restaurants survive five years, and just 34.6% make it to 10.

So one might expect the 20-year milestone to come with a month of lead-up announcements, a weekend filled with specials and events, balloons, sabered sparkling wine, and merriment all around.

But for Allen Routt and Jessica Bagley, owners of the Painted Lady Restaurant in Newberg, the 20th anniversary passed quietly, without so much as a publicly popped cork.

“We’ll wait for 50,” Routt said after harvesting artichokes from the restaurant’s garden for that night’s dinner. “One of the places I worked at recently celebrated its 50th anniversary. That is such an accomplishment. Twenty years is still impressive, and I’m so proud, but for us, it’s just another day.”

The Painted Lady officially opened its doors on May 27, 2005, meaning last week the restaurant passed two decades of fine dining in the Willamette Valley. When the couple first considered opening the restaurant in the early 2000s, Newberg—and Oregon wine country—looked very different.

Their journey began in Miami, where they met while working at Mark Militello’s restaurant, Mark’s South Beach, in 1999. They later moved to Napa and Las Vegas, but Jessica’s home state kept calling them back.

“We came up here in October 2004, and it was a day like today—crisp and beautiful,” Routt said. “We met some people, looked around, and thought, ‘Wow, there’s a lot of potential here.’”

After researching several towns across Oregon wine country, they settled on Newberg.

“We looked at Carlton, McMinnville—but Newberg had this great demographic and proximity,” he said. “It’s easy to get to from Portland, the coast, Salem, or Hillsboro. We thought it was perfect for the kind of destination dining we were aiming for.”

At the time, Routt said, Newberg was a very different community. The Allison Inn & Spa was still four years from opening. Many of today’s downtown businesses had yet to arrive. There fine dining presence was limited. The wine industry in the Willamette Valley was still emerging, and the food scene hadn’t caught up.

Still, Routt said, they sensed something brewing.

“We noticed a group of people here who really wanted something unique and different,” he said.

Much of the restaurant’s early support came from partnerships with local wineries, which helped lay the foundation for what the Painted Lady would become. Routt connected with now-established names like Chehalem, Bergström, and Argyle.

“They were so supportive right at the start,” he said. “Wineries in the area were excited about something new, and there was a feeling of collaboration. After my first meeting with Chehalem, they quickly pivoted to seeing if I wanted to help them with harvest. It was that kind of energy.”

In its early years, the Painted Lady hosted Wednesday night winemaker dinners that helped build relationships not only between the restaurant and wineries, but also among the wineries and the surrounding community.

“We’d close the dining room, partner with a winery, and serve a full pairing menu,” Routt said. “It helped connect us to the community and brought guests into town midweek.”

Routt said his cooking philosophy hasn’t changed much in 20 years. He continues to rotate the menu seasonally, focusing on the simplicity and flavor of each ingredient.

“I don’t know what it is about the dirt or climate out here, but everything grows so well in the Willamette Valley,” he said. “Sometimes, we just want to highlight the flavor of a perfect peach or fresh asparagus out of the garden.”

The restaurant’s signature dish is one he said he couldn’t remove if he tried: miso custard topped with Dungeness crab, pickled red onion, edamame, sesame powder and dashi.

“I think people like it so much because it’s poured tableside,” he said. “The experience can sometimes amplify the flavor.”

Looking back, Routt said a few moments stand out—like the early winemaker dinners and surviving the 2008 housing market collapse and the COVID-19 pandemic. He said they’re also proud of their Forbes Four-Star rating and AAA Four Diamond Awards, both of which they’re held for over a decade—and are the only restaurant in the state to do so. 

“Essentially, on an evening at The Painted Lady, everything sparkles,” states the Forbes Travel Guide. “Candles twinkle like stars, with one wall of glimmering lights and glassware set like a night sky constellation, antique mirrors and candle sconces adorn the walls and delicate white chandeliers dangle from a white-washed ceiling.”

But mostly, he’s proud of the restaurant’s quiet, consistent commitment to quality.

“We always knew Newberg had something special,” he said. “And I think people here were ready for something special, too.”