Beginning just before World War II, Jackson Street, the arterial that runs through Seattle’s Chinatown-International District (CID) and historically Black Central District, was a vibrant, nightclub-lined strip teeming with live jazz, energetic patrons, and bootleg liquor.
Jackson Street was a hotbed for jazz musicians, some of whom would go on to have international influence, including Ray Charles, Quincy Jones, and Ernestine Anderson. But, with the legalization of hard liquor in 1949, the end of music union segregation in Seattle in 1958, and the dawn of rock n ‘roll, Jackson Street’s jazz scene faded by the 1960s.
Soon, Seattle will have a permanent walking tour available to those who hope to learn more about this fascinating cultural legacy. On October 19, the Jackson Street Jazz Trail, a new self-guided tour of the jazz district that flourished on Jackson Street during this era, will launch with a multifaceted event at King Street Station as part of the Earshot Jazz Festival.
The free, all-ages event will feature a video presentation by Seattle jazz critic Paul de Barros, vintage photographs, and a performance by singer Darelle Holden, the granddaughter of Oscar Holden, an influential musician during the jazz heyday on Jackson Street. Following the event, de Barros will guide the first 15 people who sign up through the new trail.
A long journey to the trail
This 21-stop tour of Seattle jazz history is more than a decade in the making and based on information documented by de Barros in his 1993 book Jackson Street After Hours: The Roots of Jazz.
After an initial attempt to install a commemorative plaque for this historic jazz scene fell by the wayside in the early 1990s, Seattle Mayor Greg Nickels sought to revive the effort in the early 2000s by installing an informational sign at 12th Ave S and S Jackson St.
On a sunny day in 2005, the sign, featuring photographs of the musicians and explanations of the area’s significance, was unveiled in a public ceremony. By 2018, the sign was weather-damaged and defaced by graffiti. De Barros wasn’t happy about it.

“I'm looking at the sign, it's covered with tagging to the point that it's not even legible. You can't even read it. And so, I was really feeling angry about this, and feeling that it was no longer an honor to the musicians,” de Barros said.
So, with the help of Alex Rose, a creative economy advocate at City of Seattle Office of Arts and Culture, de Barros formed a coalition of community stakeholders to discuss the sign including representatives from Wing Luke Museum, Historic South Downtown, Earshot Jazz, Black Heritage Society of Washington, MoPOP, among others.
The coalition, now called the Jackson Street Jazz Trail Committee, decided that instead of tearing the sign down, they would give the damaged sign a new vinyl wrap, and they’d also create a trail through the historic jazz district that people could walk through on their own, guided by a website.
According to Stephanie Johnson-Toliver, president of the Black Heritage Society of Washington and a member of the Trail Committee, the jazz trail was inspired by Black and Tan Hall’s Seattle Green Book Self-Guided Tour. This self-guided tour launched in 2022 and spotlights Black-owned and Black-patronized businesses that existed on Jackson Street between the 1920s and the 1960s.
“There was talk of, oh gosh, we really need to focus on just the jazz clubs, right? And so it's been moving around community for a while and Paul decided to take it on,” said Johnson-Toliver, adding that while de Barros was a big reason this project got off the ground, the trail is a community effort in every sense.
“There were so many people who were contributing input and feedback...and you know what was really important too for me was that we were talking to the people that are in that community right now, the Friends of Little Saigon, The Wing Luke Museum. The intersection between the CID and Central District was very important,” Johnson-Toliver said.
Blazing the way
In 2022, the Trail Committee got a 4Culture grant to fund the sign’s refresh. They also began the process of commissioning a new vinyl wrap that would announce the trail.
The resulting sign, bursting with musical instruments and emblazoned with the text, “Jackson Street Jazz Trail,” was designed by public artist Marsha Rollinger and put up in July 2023. It includes a QR code that, as of the launch event, will take you to the interactive Jackson Street Jazz Trail website. The site includes an overview map of the trail and web pages for each of the trail stops, with backstory written by de Barros and historic photographs.

Following the first sign’s completion, the Trail Committee used the remaining grant money to do another QR code sign in the heart of Japantown, and decided it would honor of the influential women of the Jackson Street jazz scene. Tuyen Than, resident of Little Saigon, founder of CID Block Party, and co-owner of Drag & Drop Creative, was tapped to create it with her partner Ryan Catabay. This sign will be installed at 7th Ave S and S Jackson St. in the following months.
While these physical trail announcements sit along the trail path, the Jackson Street Jazz Trail officially starts at King Street Station at 3rd and Jackson St. This station is how jazz first came to the Emerald City when African Americans began to migrate to the area by railroad at the turn of the twentieth century.
From there, the trail highlights sites like 662 ½ South Jackson Street where The Black Elks Club once stood. It was at this Black social club that Ray Charles's Maxin Trio played its first gigs in 1948.
Other notable sites include: 209 Fifth Avenue South, previously the Dumas Club, the first African American social club in Seattle that opened in 1912; a lively smoke shop and venue called Two Pals; and the original site of the Black and Tan, one of the strip’s most popular and longest-running integrated clubs.
In the future, de Barros hopes there will be bronze plaques with QR codes at all the stops of the trail. For now, interested trail-goers should go to King Street Station, use their smartphones to hop onto the tour website, and then guide themselves through this historic jazz neighborhood.

Preserving key history
In the process of working on this tour, de Barros has uncovered new insights into the neighborhood’s jazz legacy that he hopes can deepen the collective understanding of Seattle’s rich cultural history.
“When you take on a project like this, it never leaves your mind,” said de Barros, referring to his more than thirty-year exploration of local jazz history. “It's never finished. They're always these questions. When I went back into this [trail], I thought, well, maybe this is an opportunity to clear up some of the questions that I had.”
For instance, when de Barros was writing Jackson Street, he had questions about the location of Basin Street, a successful nightclub in the district owned by African American entrepreneur Dave Lee that offered jazz and gambling 24-hours a day.
He had an address for the club, 413 Maynard St., which in the 1990s led to the street level entrance of the Bush Hotel, next door to Hing Hay Park. He assumed that this door must’ve been the Basin Street at one time, but he wasn’t positive. He quelled his doubts and moved on.
“When I was writing the book, I didn't really have the time to go looking at archival photographs of buildings that have been torn down to try to figure out stuff like this. I was trying to get the story of the jazz musicians,” he said.
With the jazz trail project, it was necessary to dig into photographs from the Washington State Archives, so he took another look for Basin Street. De Barros discovered that the Olympus Hotel, which has since been torn down, used to stand where Hing Hay Park is now. That was where the Basin Street was, and in 1941, 413 Maynard Avenue South mapped to the Olympus Hotel building.

That wasn’t all he discovered: “When the Japanese internment happened in 1942, the Japanese businessperson who owned the Olympus Hotel sold it to Dave Lee...I think this was a fascinating revelation, that two communities of color that were both being oppressed by the United States government wound up being in competition at this particular point,” said de Barros.
As de Barros suggests, Jackson Street’s jazz district bustled during what was, for many in the neighborhood, an ugly time. After all, the communities of color who lived and owned businesses in the CID during this era were there because of racial tensions and redlining, a discriminatory practice that restricted where people of color could exist in Seattle.
“But the fact that they overcame that and that white jazz fans and musicians like Jimmy Rowles, the great piano player, could come down here and mix with [Black musicians] Palmer Johnson and Oscar Holden in a nightclub owned by [Chinese businessman] Charlie Louie...is inspiring,” de Barros said.
Looking back to go forward
Redlining as a formal policy in Seattle ceased by the end of the 1970s, but the legacy of this racial discrimination is still felt in the area.
After decades of loan rejection and inadequate investment, the CID continued to have deflated real estate values until around 2000. At that point, prices rose and gentrification began. Many families of color in these neighborhoods were displaced and cultural histories were buried beneath new development.
For those who live and work in these neighborhoods, the fight to uncover, preserve, and celebrate the history and culture in the CID and Central District is ongoing, and the new Jazz Trail contributes to that effort.
“We want to celebrate. Little Saigon and Japantown and Chinatown, like, the whole narrative of struggle and struggling is constant,” Than said. “And so having something that's really joyful and shows...that this isn't a scary neighborhood to be in.”
Johnson-Toliver found this project to be a powerful way to nurture the friendship between the communities in the CID and Central District.
“Many of the clubs that were through the CID were owned by Asian families or organizations, but then they would lend and lease these places to Black people who were then being the entrepreneurs of those spaces...” she said.
“And so having the opportunity to revisit that history and decide on what we still have in common... allowed us, in community, to revisit how we really did work together to be able to support our communities and our music and our recreation.”

Today, the CID is still recovering economically since the pandemic, and was named one of the “most endangered historic places” in the U.S. in 2023. The neighborhood deals with “profound challenges to public safety, a surge in homelessness, and an alarming increase in anti-Asian hate crimes,” according to Northwest Asian Weekly. This is particularly evident around 12th and Jackson Street, which was identified last July as a crime and drug “hot spot” by the Seattle Office of the City Auditor.
For his part, de Barros thinks of the Jazz Trail as an unofficial part of Mayor Harrell’s Downtown Activation Plan, a strategic plan announced in 2023 to reinvigorate and transform Seattle’s downtown. He hopes the trail will help to drive business and recovery in the area.
“We're not going to fix the problems by having people walking through with their phone following a jazz tour. I know that,” he said. “But it can be a positive element in the community, and we need as many as we can.”
Editor's note: Alexa Peters and Paul de Barros are working together on a book about modern Seattle jazz, which is not directly affiliated with the Jackson Street Jazz Trail.