My name is Owen Bailey and I am running to serve as 1st Ward Council member for Chestertown.




About Owen

I was born at Kent & Queen Anne’s Hospital (now the University of Maryland Shore Medical Center at Chestertown), and attended school in the area from Kent School to Washington College where I received a Master’s Degree in English in 2009. Last year my wife Nanna and I bought our home on Richard Drive, and in the time since we have enjoyed working on our home and garden, meeting our neighbors, and getting to know the neighborhood better on our walks with our dog Daphie.

My professional experience has primarily been working for nonprofits. While I was a master’s student, I worked at the Rose O’Neill Literary House, helping to bring guest authors to campus, working with students on the student run newspaper and literary magazines, and helping to organize visits from prospective students. In the summer of 2015, I made the jump out of the academic world into the environmental sector and joined the Eastern Shore Land Conservancy. Today I work at their office in Easton as the Facilities and Administrative Coordinator where I help manage the three buildings on our campus, work with our partners, and process donations.

I spend much of my spare time volunteering for various nonprofits in Chestertown. For four years I was the President of the Chestertown Book Festival, in which time we brought many talented authors, including nonfiction writers, children’s authors, and journalists. Currently I am the Membership Chair for the Friends of the Kent County Public Library as well as the Education Chair for Colchester Farms CSA. I value the role nonprofits serve in the community and see firsthand the positive changes they bring.

In my professional and volunteer career I have helped organize budgets, coordinate and work with volunteers and contractors, manage outreach efforts, plan fundraising campaigns, and manage grant writing and reporting.

For most of my life Chestertown has been my home and its residents have been my closest and most valued friends. This town has many wonderful qualities and assets, but there is much room for improvement as it can better serve its residents and guests.


1st Ward Platform

  • Represent all residents of Chestertown’s 1st Ward by being a committed, available, and active member of the Town Council
  • Increase recreational opportunities
  • Ensure residents have access to job training and employment aid
  • Work with the local police force to ensure public safety
  • Encourage smart development on river and throughout the town
  • Improve pedestrian safety
  • Improve storm water runoff throughout the town
  • Promote sustainability at residences and businesses
  • Hold quarterly meetings with residents of the 1st Ward


The Board of Supervisors of Elections for Chestertown, Maryland, by authority of the Charter for Chestertown, Maryland, gives notice that an election will be held on Tuesday, November 7, 2017 for the purpose of electing a Mayor and Councilmembers in the First and Third Wards.

All Town of Chestertown registered voters will be eligible to vote for Mayor. All registered voters in the First Ward will be eligible to vote for the Councilmember candidates in the First Ward. All registered voters in the Third Ward will be eligible to vote for the Councilmember candidates in the Third Ward.

Important dates:

There are no upcoming events at this time.