Former Mayor Margo Bailey laying a wreath at Memorial Park on the 10th anniversary of 9/11. Photo by Dan Menefee

Former Chestertown Mayor Margo G. Bailey died September 1, 2020. She was 76 years old.

Born October 29, 1943, she was raised in Florida and moved to Chestertown in 1972. She was married to the late Bill Nicholson, then the town manager, with whom she had three daughters, Nancy, Maren and Carrie.

Bailey later married W. Michael Bailey, Economics Department Chair and the inaugural Hodson Trust Professor of Economics at Washington College. The Baileys raised their family at their home on Washington Avenue.

In 1991, Bailey followed her husband onto the town council after she had gaining political traction in the late 1980s fighting the RESCO incinerator plant proposal.

She ran for mayor in 1993, beating longtime councilman Vito Tinelli and David Proctor. Bailey’s success came from running an anti-Walmart platform. The project on the northern edge of town went down in flames in June 2001 after an eight-year fight. Bailey would fend off a comeback challenge by Horsey in 1997.

Bailey also mounted a green agenda that included her successful effort to ban plastic bags from Chestertown retailers in 2010.

Bailey announced her retirement in 2013, endorsing Chris Cerino among a crowded field of seven candidates.

“Margo was a consensus-building Mayor who was patient about achieving her social and political goals,” remarked longtime Chestertown Town Manager Bill Ingersoll, who remembered meeting Margo when her then-husband Bill Nicholson hired Ingersoll on Sept. 1, 1975.

“She died 45-years to the day I was hired by the town,” Ingersoll said.

When the Garnett elementary school needed a new playground, she organized the community into building a Robert Leathers creation that was designed with the input of the children,” Ingersoll said.

“Margo was a counter-puncher by nature and because she was the first female Mayor she often had to use those skills,” Ingersoll continued. “She was relentless with environmental concerns, receiving several national commendations and is well-known for her successful removal of lightweight plastic bags from our Town stores. However, Margo is most famous for leading the charge to keep Walmart from building a mega-store just outside of the Town’s boundaries.”

Bailey was honored as Grand Marshal of the 2015 Chestertown Tea Party Festival parade.

Bailey was predeceased by her husband, Michael in 2006. In addition to her daughters, she is survived by her son, Owen Bailey, and her stepsons Joel, Eric, Keith and Colin Bailey. Her youngest son, Owen, was recently appointed to the Chestertown Planning Commission.

“Margo was both a friend and a mentor.  She was a tireless advocate for Chestertown and worked extremely hard to improve the quality of life for all of our residents,” said Mayor Chris Cerino. “The Gilchrest Rail Trail, Bailey Park, Gateway Park, the Town’s recycling program, and the renovations at the Chestertown waterfront are just a few of the projects that she either initiated or completed during her twenty years as Mayor.  While Margo’s passing is sad news for all that knew her, the legacy of public service that she leaves behind will live on for many years to come.”

Details on funeral arrangements were not available at press time.

Kent Pilot Reporter Dan Menefee contributed to this story