Meet Winchester's Town Manager

Winchester’s Town Manager, Josh Kelly, joined the Town of Winchester's service on April 19th, 2021, after being selected for the position by the Board of Selectmen in February 2021. He is Winchester's 29th Town Manager.

From 2015 to 2020, he served in multiple capacities within the Town of Waterford's government, where he was a resident. Josh was first elected to the Waterford Zoning Board of Appeals in 2015, followed by appointment to the Inland Wetlands & Conservation Commission in 2016, and he was elected to the town's legislative body, the Representative Town Meeting, in 2017. During and immediately after his graduate studies, he served as a Graduate Assistant and Management Analyst for the Town of Windsor, CT (2018 - 2019). Most recently he served as Town Administrator in Bolton, CT (2019 - 2021). A Connecticut native, Josh gained other related financial, community engagement, and project management experience through employment and volunteer opportunities with Suicide Prevention & Crisis Services of Ithaca, NY (2013 - 2014), the Office of Congressman Joe Courtney (2015), Wheaton College, MA (2015 - 2017), the University of Connecticut (2017 - 2018), and more.

Josh's priorities in Winchester/Winsted have included, but are not strictly limited to promoting further economic development and business growth in the downtown corridor; connecting at-risk residents with the social services they require to not just survive, but thrive; increasing Town communications to residents; and improving the town's critical infrastructure.

Josh earned a bachelor’s degree in Political Science with minors in Sociology and Public Policy from Wheaton College, MA in 2017 and a master’s degree in Public Administration from the University of Connecticut in 2019. He is a member of the International City/County Management Association, the Connecticut Town and City Management Association, and the Connecticut Council of Small Towns Board of Directors.

In his spare time, he volunteers for charitable and educational organizations, including Project Bright, and the Wheaton College Model United Nations Alumni Association, and enjoys hiking, kayaking, and reading. He has been a resident of Winchester since April 2021.

In the office, Josh can be reached at or at 860-738-6962. Josh also manages a number of social media and web-based sites in his capaicity as Town Manager, including a Facebook page, Twitter account, LinkedIn profile, and website.