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What's Up Magazine

Margo Bailey

Mar 23, 2011 03:00AM ● By Anonymous


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Bailey recently entered her 15th year as Mayor of Chestertown, a quaint, picturesque, Revolutionary War-era town situated on the banks of the Chester River.

“One of the biggest challenges we face as a town is how do we grow and still keep our sense of place? How do we stay connected as human beings?” says Bailey, when pointing out some of the challenges that face her as mayor of a town of 5,000 people. “How do we allow our town to grow and still keep it visually what we want it to be?”

Perhaps the challenge for which Mayor Bailey is most famous involves the town’s battle against Wal-Mart. Residents didn’t want the big-box retailer to build within incorporated town limits, so a decade-long legal battle ensued, eventually ending with no Wal-Mart and a new law restricting retail buildings over 60,000 square feet.

“When you live and work in a small town, you know the small business owners,” she says, when speaking about the Wal-Mart battle. “These are people who have lived here all their lives; they contribute to the community; they donate things and volunteer their time to nonprofits. Are we supposed to tell them, ‘Too bad, but we’d rather save 50 cents on a pack of Pampers’? There are too many businesses at stake.”

Bailey knows what it’s like to balance work and family. She’s raised four children: Nancy, 37, Carrie, 33, Maren, 29, and Owen, 24. And she has two grandchildren: Greta, almost 3, and Nick, 6 months.

So what is the key to the classic juggle between home and office? “I think the key is setting a time frame. Family always comes first,” says Bailey. “I never wanted to raise latchkey kids. I don’t work on weekends unless it’s an emergency, don’t take phone calls at night, and when my kids were coming home from school at 3:30 p.m., I was available to them.” She also credits her now-deceased husband, a former professor at Chestertown’s Washington College, who was home in the evenings while she attended town meetings and shared equal responsibility in raising the children.

Bailey grew up in Coconut Grove, a town in South Florida that provided inspiration for her later run as mayor. She graduated from the University of Maryland with a degree in English Literature, and then continued with English Literature graduate studies at Washington College. She wanted to major in dance, but her dad wouldn’t let her. She married Chestertown’s town manager in 1974, but the marriage didn’t work out. She stayed on in Chestertown to run things—first a family, then a newsstand (where she first began to listen to the local people and their needs), then the town itself.

The environment is a key issue on Bailey’s agenda. She was the first mayor on the Eastern Shore to sign the U.S. Conference of Mayors Climate Protection Agreement.

“We can’t turn this train around,” she says, describing today’s biggest town challenge on the global level. “We need to reduce our carbon footprint. It is so difficult to get people to change their living habits. You don’t want to have to keep legislating it. We’d really like to make some headway without adding more laws.”

Margo Bailey learned she had leukemia in 1990—and has fought the diagnosis ever since. After her unsuccessful first marriage, she found happiness in a second marriage. But last year, she lost both her second husband and, unexpectedly, her best friend. She has been threatened legally and personally as a result of several challenging professional and personal situations over the years, often by men who resent a successful woman in power.

She has a small office immediately inside the entrance to Town Hall. Her door is always open (“I close it,” she says, “only in a highly private meeting.”) so that citizens feel welcome coming in at any time to discuss a town issue or other concern. “If you can’t have that kind of accessibility here in a small town, where can you have it?” Bailey wonders. Chestertown was named by the National Trust for Historic Preservation as one of its Dozen Distinctive Destinations in the United States.

Mayor Bailey keeps her own schedule, choosing not to rely on staff for what she feels is an unnecessary administrative cost to the taxpayers. She also continues to work part-time at the local book shop so that she can remain connected to the community and local businesses. “We have a gorgeous waterfront small town,” says Bailey. “There’s a mix of artists, wealthy citizens, and business owners who help the town thrive. We must keep that mix.”With all the challenges that any mayor faces, what is it that keeps Margo Bailey getting up each day and showing up to lead her town? “Some people pay attention,” she states. “It is really nice once in awhile to get that rare ‘Thank you.’ It gives me a charge in a normally thankless world. Being mayor is a 24/7 job—you never stop thinking about it; it’s truly an all-consuming job. But I want Chestertown to continue to be the quaint town where I raised my kids.”

She smiles. “I think my son has climbed every tree in this town.”

Mary T. McCarthy is a professional writer and a former Centreville (county seat of Queen Anne’s County) Town Council Member. Mayor Margo Bailey provided tremendous inspiration during Mary’s three-year term in office.