Ashland officials kick off long-range, community-focused strategic planning effort

Sara Wilson, owner of SSW Consulting, leads Ashland’s first strategic planning session Wednesday, Jan. 29, at Pioneer Hall. Nearly 20 city officials attended the meeting. Damian Mann photo for Ashland.news.
January 30, 2026

City leaders and staff spent six hours outlining priorities for the decade amid financial strain, wildfire threat and demographic change

By Damian Mann for Ashland.news

Ashland city officials took a deep dive Wednesday, Jan. 28, into a first-ever community-focused, long-range strategic planning effort.

At Pioneer Hall, almost 20 city officials and councilors spent six hours scoping a path for a better future over the next five to 10 years despite ongoing financial and political pressures.

“We want to really lean into what this community needs,” Councilor Dylan Bloom said.

Councilors stressed reaching out to the community and to local institutions such as the Ashland Chamber of Commerce, Southern Oregon University, and the Oregon Shakespeare Festival.

Bloom said local institutions, many of which are struggling financially, have largely operated independently and he hoped to cultivate more collaboration.

“At the end of the day, we in Ashland have a tendency to be siloed,” he said.

Ashland officials developed a graph showing how the city has changed over time, from the hippie era in the 1960s to the more affluent community of today. Damian Mann photo for Ashland.news

With guidance from SSW Consulting of Lake Oswego, the officials reviewed the past to determine how the city reached a point where institutions struggle, and they produced a meandering timeline that looks like a design for a Rube Goldberg gadget.

Transformations of the city have occurred from the time Angus Bowmer founded the Oregon Shakespeare Festival in 1936 to the hippie era in the 1960s and 1970s, and the creation of the Ashland Food Co-op, which has become a community hub.

Earlier, housing was plentiful, and school enrollment was on the rise.

Over the past 20 years, housing has become expensive, enrollment has declined, and the threat from wildfires has mounted.

Sara Wilson, owner of SSW Consulting, said the community has grown older and wealthier, though there has been an uptick in younger adults ages 18 to 24 since 2022.

Themes developed during a strategic planning session of the Ashland City Council and city staff. Damian Mann photo for Ashland.news.

The city’s population was 21,343 in 2023 and is expected to grow by 23%, or 5,1268, between 2025 and 2070.

Minorities represent a small portion of the population, with Hispanics at almost 10%, though that percentage dipped slightly in the past few years.

Over the next few months, community outreach, workshops, brainstorming and creation of leadership teams will lead to an action plan that could be adopted by the council in August.

Wilson said her team has had some discussions with the community to gauge what interests residents.

“The ice rink was not well-received,” she said. The city was not able to open the ice rink this season, upsetting many local families.

Mayor Tonya Graham said that without fundamental changes to the city, “We’re going to continue to be wealthier and older.”

In addition, she said the city faces uncertainty from an increasingly unreliable federal government.

Councilor Bob Kaplan said he’d like to see a strategic plan that resembles the community wildfire plan, which addresses both the forests above town and creates more defensible space around homes.

“The city should become a fire break, not a fire source,” he said.

Against this backdrop, city officials developed a list of themes that might guide policies going forward.

One of the major themes was preparing for uncertainty by being flexible, nimble, innovating and developing partnerships with local organizations.

Other themes included support for children and families, providing adequate recreational opportunities, managing change, developing good-paying jobs, creating a more diverse economy, changing systems to streamline local government, building resilience, developing a strategic plan with a clear vision, and finding ways to ease financial tensions.

The city itself is likely to face further service cuts over the next few years.

Kaplan said the city needs to look internally at how it functions and also reach out to the community, businesses and institutions.

“What is it that only the city can do?” he said. “What is it that they need from us to be successful?”

Councilor Gina DuQuenne said community outreach must include one-on-one conversations with residents to determine their needs.

“It’s got to be bigger than a survey,” she said.

City Recorder Alissa Kolodzinski suggested that the council consider including staff in the development of the strategic plan, as it will be up to staff to implement it.

Wilson with SSW Consulting said it’s important to have staff “buy-in” and engagement.

“They’re the boots on the ground,” she said.

Councilor Kaplan said staff would provide a sense of realism to the goals of the strategic plan.

City staff also said it has become more difficult to hire and retain new employees. The city has had a 30% turnover in the past five years.

Ashland Fire Chief Marshall Rasor said, “There has been a shift in the younger generation wanting more time off.”

He said that has caused scheduling problems.

City Manager Sabrina Cotta said, “Different generations have different priorities.”

She said the city is generally viewed as less attractive to work in, with more “hostility” toward city employees.

Cotta, while discussing potential strategic planning, said some ideas are based on good intentions “but are difficult to put into practice operationally.”

When officials broke into three teams to develop separate visions of a better future, one of the teams concluded that lofty goals were difficult to attain unless the city’s budget problems were resolved first.

“We were grounded in reality,” said Councilor Derek Sherrell. “We need to make sure we have the funding to enact the plan.”

Sherrell said his team, which included city Finance Director Bryn Morrison and city Public Works Director Scott Fleury, focused on “living in the now.”

He said there are many issues that the city is unable to solve, such as the climate crisis, homelessness or burdensome state laws.

He said the city’s Charter could potentially be rewritten, and the city should focus on infrastructure and developing better finances.

“Until we get these things right, we won’t look to the future,” he said.

Another team led by Brandon Goldman, director of Community Development, offered a more aspirational scenario.

He said the future should offer more opportunities for families, including possibly a “baby boom,” a new Butler Memorial Bandshell, music festivals, the development of an incubator system to help new businesses get started, and “the ice rink in full use.”

“People born here can live here and die here,” he said.  City Manager Cotta led a team that also offered an optimistic future that envisioned a more family friendly community.

A local trolley, a pedestrian-only downtown Plaza, and 10 things to do at East Main Park were some of the ideas that would offer residents more options.

“Go us,” Cotta said.

After the presentations, Councilor Kaplan said, “I didn’t hear anybody say they wanted to lean into an elite community.”

Reach freelance writer Damian Mann at dmannnews@gmail.com.

Picture of Steve Mitchell

Steve Mitchell

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Ashland city officials met Wednesday to kick off the city’s first community-focused, long-range strategic planning effort, spending six hours reviewing the city’s past and debating priorities for the next five to 10 years.

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