Executive Director of Portland Trails Announces Departure
Kara Wooldrik to Step Down at the End of 2022 After a Decade of Leadership



Portland Trails, a non-profit urban land trust that transforms Greater Portland into a healthier and better-connected community through a 70+ mile trail network, announced today that Executive Director Kara Wooldrik has decided to step down from her role at the end of December 2022.

Portland Trails Board Chair, Kate O’Brien, said “Kara has passionately served in leadership of Portland Trails for 10 years and has been instrumental in ensuring the people of Greater Portland have safe and equitable access to a high-quality trail network that encourages active transportation and connection throughout our communities.  While we are sad to see her go, we are grateful for her many contributions and look forward to opening up the organization to our next generation of leadership.”

In her decade as Executive Director, Kara oversaw the expansion of the trail network so that every residence in Portland was within a ten-minute walk of a trail or greenspace, connecting communities throughout Portland, South Portland, Westbrook, and Falmouth. Specific highlights from her leadership tenure include:

  • - Initiated the innovative 15x15 Annual Meeting format in 2013
  • - In 2015 started placemaking initiatives in East Bayside, including Gould Street Commons, Boyd Street trail, Anderson Street connector trail and the start of the City At Your Feet Scavenger Hunt to create more access to recreation and transportation opportunities in neighborhoods that had been underserved public spaces.
  • - By intentionally prioritizing the daily lives of every resident, Portland Trails, in collaboration with dozens of partners has created a network of trails and greenspaces that is within a 15-minute walk of all Portland residents.
  • - Partnered with the City of Portland to create the weekly Sundays on the Boulevard events.
  • - Partnered with dozens of businesses across Greater Portland to, encourage walking and cycling to workplaces, community centers, businesses, concerts and events throughout the year
  • - Challenged Board and Staff to expand Diversity, Equity, Inclusion, and Belonging understanding, and relating it to the Portland Trails Mission, including participating in the First Light Learning Journey.
  • - Led Portland Trails through the pandemic, keeping our organization funded and trails open and accessible when the community needed it the most.
  • - Spearheaded our multi-year Neighborhoods Project, to make the trails welcoming for all our community members
  • - Expanded relationships with area employers to increase engagement through financial support and year-round volunteer community-building activities.
  • - Oversaw land acquisition and trail expansion:
    •         - Berle Mile Pond - Falmouth
    •         - Conant Property - Westbrook
    •         - Canco Woods - Portland collaboration with neighborhood organizers and Trust for Public Land
    •         - Two 1-mile extensions of the Stroudwater Trail


“Over the past ten years, I have been honored to build and lead an organization that continues to have such a tremendous impact on the health, wellbeing, and sustainability of the Greater Portland area,” says Kara.  “What a gift it has been to steward this organization of passionate people from diverse sectors and perspectives. Across our different fields, geography, business cultures and missions, we have worked together on a shared vision to create healthier communities. And that still inspires me every day! I am incredibly grateful to the thousands of members, volunteers, partners, and funders for their continued collaboration and support.”

Kara’s efforts and impacts have been as much behind the scenes as they have been in the public eye. She’s helped us shift how we measure and frame Portland Trails’ efforts, impacts, and outcomes. Moving us from “miles of trails and acres preserved” to “healthier and more connected communities created” has helped facilitate a widening recognition of the many benefits that a trail network like ours can have on individual lives, communities, and local economies. By bolstering our organization’s internal operations, systems, practices, and culture, Kara has helped ensure that the Portland Trails you’ve come to know and love is stronger than ever.

Kara’s influence on trails reached even beyond our shores. In 2019, she leveraged her Portland Trails expertise at conferences and workshops in Japan and South Korea to offer insights into the various benefits of trail networks and the community-building nature of constructing trails.   In Japan, she joined an international team to consult with local officials on the ways trail networks can help facilitate transportation and wellbeing during and after natural disasters.  In South Korea at the Asia Trails Conference, she was the keynote speaker on creating town-city trail networks.  After her departure from Portland Trails, Kara plans to stay active with the World Trails Network.



Former Board Chair Andy Abrams said, “The Greater Portland community benefits every day from Kara's vision to make our trail network even more sustainable and meaningful. Her recent work to educate our Board and Staff to challenge our responsibility to Wabanaki people is just one example of her well-informed influence. Her quiet, thoughtful and strategic ability to convene and collaborate and build relationships with leaders across Greater Portland and across the world has been important to strengthening the health and sense of community of this place. The impact of her efforts will continue to be felt over the next 100 years.”

The Portland Trails Board will be conducting a national search for a new Executive Director, commencing January 1. The new leader will be well positioned to participate in the 2023 Strategic Planning process.

A job description will be available shortly on https://clone.trails.org/about-us/jobs/