July 12, 2025
Winter Park Town Manager Keith Riesberg announced his planned resignation today after nearly seven years of leading the Town of Winter Park organization. Since his appointment in 2018, Riesberg has been instrumental in guiding Winter Park through a period of significant evolution and development.
“Keith’s leadership over the past five years during my time as Mayor has been nothing short of transformative for Winter Park,” said Mayor Nick Kutrumbos. “He brought vision, professionalism, and a deep commitment to our community, guiding us through a time of tremendous opportunity. While we’re sad to see him go, we’re incredibly grateful for the strong foundation he’s helped build. His impact will be felt in Winter Park for many years to come.”
Riesberg’s tenure is marked by several key accomplishments:
Expansion of Workforce Housing
Under Riesberg’s leadership, the Town initiated several critical projects to address the community’s shortage of affordable housing. Hideaway Junction Phase II and the Fireside Creek Apartments provided new, affordable workforce housing with both ownership and rental options. Creating the Fraser River Valley Housing Partnership through a voter-approved property tax provided a long-term solution to funding future affordable housing initiatives.
Enhancement of Transit Infrastructure
The Town has made significant strides in improving transportation, including developing a new transit center at Cooper Creek Square to enhance connectivity within the town and to the resort and expanding regional partnerships to increase The Lift bus service to Granby. The completion of a $23 million transit maintenance facility has positioned The Lift bus service to deploy electric buses, which is set to begin later this year. Additionally, steps for forming a regional transit authority are underway to finance and operate new public transit infrastructure, including the town-to-resort gondola.
Imagine Winter Park Comprehensive Plan and Foundation Planning Initiatives
With Riesberg at the helm, the Town adopted the “Imagine Winter Park” comprehensive plan to guide future development and establish a common vision for land use, public services, and economic development. The Downtown Plan, Three Mile Area Plan, and the Parks, Trails, Campground and Open Space Master Plan soon followed. Each provides a specific framework for short-term, mid-term, and long-term actions to guide the evolution of Winter Park and ensure its alignment with community goals.
Annexation of Key Properties
The Town annexed key properties over the past seven years, including Beaver Village Condominiums and Cooper Creek Village. These properties provide easements that will be required for the gondola connection to Winter Park Resort and the ski-back trail to downtown.
Trail Expansion and Investment
Over the past seven years, Winter Park has significantly expanded its trail network, reinforcing its reputation as a top outdoor recreation destination. Key projects include repaving 1.6 miles of the Fraser River Trail, planning for the Fraser River Trail’s relocation adjacent to the river, and improving the Vasquez Creek Trail to stabilize the riverbank and allow people to actively engage with the river.
Winter Park Unlocked Master Plan
Perhaps the most extraordinary initiative in recent years is the advancement of the Winter Park Unlocked Master Plan. Winter Park Resort’s visionary $2 billion redevelopment initiative will make notable improvements to the resort and the community, including 350+ acres of new skiable terrain, new public amenities such as trails and parking, a gondola connecting downtown to the resort, and new hotels, restaurants, and public spaces.
To ensure the sweeping transformation serves the best interests of the community, the Town has played a significant role in shaping plans and investments. The formation of the Winter Park Urban Renewal Authority (URA) in 2024 allows the Town to guide smart development by focusing on funding infrastructure and public amenities that align with the community’s vision.
The Town exercised further leadership with the creation of the Regional Infrastructure Cooperation Agreement (RICA) to support the resort’s expansion and infrastructure needs. The collaborative agreement between the Town of Winter Park, Alterra Mountain Company, and associated metro districts focuses on funding and constructing necessary infrastructure projects.
“I’m incredibly proud of what we’ve accomplished together in Winter Park,” said Town Manager Keith Riesberg. “It’s been an honor to serve this community and work alongside such dedicated staff and leadership. This was a deeply personal decision, driven by the desire to be closer to family. While it’s difficult to step away, I leave knowing the town is on a strong path forward.”
Riesberg’s last day will be September 12, 2025. He will continue his career in public service as City Administrator of Rolla, MO.
The Town Council will initiate a comprehensive search process to identify a new Town Manager who will continue to advance Winter Park’s strategic objectives.
Learn More and Apply
To learn more about the Town Manager position and the qualities Winter Park is seeking in its next leader, please review the recruitment brochure. The deadline to file your application through Columbia ltd is September 14, 2025.
