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What's Up Magazine

Our Historic Downtowns

Jun 28, 2013 07:57PM ● By Anonymous


Founded in 1710, Easton has a long list of claims to fame—both past and present. The Third Haven Meeting House, the oldest Quaker meeting house and one of the oldest places of worship in Maryland, is located in Easton. During the days of the Eastern Shore Baseball League, Easton was home to four of the league’s franchises (the Farmers, Browns, Cubs, and Yankees). For more than 40 years, Easton has welcomed 17,000-plus visitors during its annual Waterfowl Festival, which is dedicated to wildlife conservation, the promotion of wildlife art, and the celebration of life on Maryland’s Eastern Shore. And the preservation of the historic Avalon Theatre, built in 1921, has given the entire Mid-Shore region an active artistic hub.

There are other successes, as well, says Easton Mayor Robert Willey, including the refurbishment of the Tidewater Inn and Easton Market Square, the growth of the Academy Art Museum as a thriving community arts center for students and visitors of all ages, and the relocation of destination-worthy Jean McHale Antiques, Design and Fine Art to Easton from Baltimore.

“Downtown Easton is starting to get some ‘glitz’ around it,” Willey says. “Downtown is the heart of Easton, and you don’t let the heart die.”

“Putting on the glitz” is not without its challenges, though, Willey says, noting that renovations of historic properties can be expensive, and shops located in the Historic District are necessarily smaller than mall stores because of the limited square footage available in older buildings.

“You also need activities to bring people into downtown, especially younger people,” the mayor says. And while Easton already has shopping, restaurants, and theaters that can draw people in, “we need to build on that synergy,” Willey remarks, adding that Easton’s civic and business leaders alike are exploring “progressive” approaches to bring more affordable housing to the downtown area, redevelop the 11 acres of waterfront at Easton Point into a public park, and provide improved public transportation.

Restaurant owner Amy Haines, who moved to Easton from San Francisco and opened Out of the Fire in 2000, is an enthusiastic supporter of Easton and is pleased at the progress she has seen in the years since she moved to town. “A lot of great things are going on now,” says Haines, who was drawn to Easton not only because it reminded her of her childhood in New England, but it also gives her the sense of community she was seeking. “I have the opportunity here to see so many people I know just walking down the street,” she says.

Haines, who also serves on the Board of the Talbot County Office of Tourism, recalls that downtown Easton wasn’t a big attraction in her early days in town, despite the fact that with its access to Route 50, it should be “bustling.” But times have been changing.

One of those changes has been the recent creation of the Easton Downtown Partnership, an independent group formed to attract new visitors and residents to Easton, as well as serve the existing businesses and their clientele. “We want to create a more cohesive feeling,” says Alice Lloyd, proprietor of the Bartlett Pear Inn and one of the organizers of the partnership, along with representatives from Cottage Studio and Gallery, Studio B Gallery, Miranda's Shoes, Due East, and the Clay Bakers.

Although the group is an independent organization, its members are working closely with Mayor Willey “for the good of both the town and its businesses,” Lloyd says. The group's accomplishments so far include the creation of an updated town map, the design of a new town logo, and a soon-to-be-live website ( More projects are in the works and more and more business owners are lending their support to the group’s goals and efforts.

“Easton has never before had such a partnership that speaks for all the businesses in town,” says Lloyd, a native Eastonian who believes historic downtowns aren’t “just about old things.”

“There is so much new and unique within the history of the buildings, the town itself, and the friendliness of the people who live and work here,” she says. “We're about keeping history alive, enriching the appeal of downtown, and confirming why we’ve all chosen Easton as a home base.”

Despite its newly invigorated sense of vitality, challenges still remain for downtown Easton, says Amy Haines, who would like the district to offer more green space, walkways, and second-story residences above the shops. She hopes the efforts to revitalize and promote downtown Easton will provide more people with the healthier lifestyle she says she has found since moving to town.

“When you live in a town like Easton, you know your neighbors, you know with whom you’re doing business, and you enjoy a more honest way of living,” she says.


Four years older than Easton, Chestertown was founded in 1706 and, soon thereafter, was named one of the Colony of Maryland’s six Royal Ports of Entry. A shipping boom followed and, considered at the time Maryland’s second leading port, the town enjoyed much prosperity. The growing merchant class of the time built the gracious brick mansions and townhomes, many of which still remain today; indeed, Chestertown is second only to Annapolis in its number of existing 18th century homes. Another point of pride is Washington College, founded in 1782 (George Washington himself was a founding patron) and the 10th oldest college in the U.S.

But despite its many past successes, Chestertown, like other historic towns—indeed, like most downtowns, large and small, throughout the country—has faced its share of difficulties in recent times. But to understand how to reinvent themselves, towns like Chestertown must understand why downtown districts have died in the first place, says Mayor Margo Bailey.

“Shopping centers were the first stake in the heart,” Bailey says. Chain stores finished off local mom-and-pop shops, then “big box” stores, located on the perimeter of downtowns, further siphoned off customers who were drawn to sites where they could get everything under one roof. Add to that the recession, outlet malls, and Internet shopping, and you’ve got very little reason to venture downtown.

Chestertown has fared better than many other downtown areas, according to Bailey, because generations of residents have protected the fabric of the town, maintaining the many historic residences and storefronts. “The town looks good,” Bailey says. “We have not rested on our laurels. When we could improve, we did so.”

What will drive the new economy—which, in turn, will revitalize the downtown core, according to Bailey—is younger people who want to live just steps from restaurants and shops, and if possible, work from home. To attract those prospective residents, Chestertown is taking a hard look at its assets and determining what its strengths are and how it can capitalize on them. One example, Bailey says, is Chestertown’s waterfront, which, she admits, “hadn’t been used to its best advantage.” To make sure residents and visitors alike will have a multifunctional waterfront area, the town bought the existing marina to ensure that it didn’t fall into private hands.

“We have a river, we have a college, and we have an arts community,” Bailey says, noting that community activists and government officials are working together in partnerships, such as the Chestertown Renewal Initiative, to bring into being a vision for Chestertown’s future that “won’t change our essence, but will enhance what is already here.”

Rebecca Flora is a recent transplant to Chestertown, who moved to the area from Northern Virginia because she was attracted to its “core assets”—its architectural integrity, walkability, outdoor recreation opportunities, and sense of community. “There’s a different pace…a different kind of feeling…when you cross the (Bay) Bridge,” says Flora, whose professional life as a consultant on the creation of sustainable communities mirrors the personal values that led her and her husband to relocate to Chestertown.

Flora, who has become active in town affairs, suggests that downtown districts such as Chestertown’s can evolve and thrive if they maintain what makes them unique and don’t try to be something they’re not. “A town like ours will always have a small economy,” Flora says. “But we can attract people (like myself ) who, by virtue of today’s technology, can live and work almost anywhere, and we can provide unique services (such as the town’s artisanal bakery, Evergrain Bread Company) that you won’t find elsewhere.”

Longtime resident and business owner Carla Massoni—who has lived in Chestertown since 1985 and has owned a hotel, restaurant, two retail stores, and now a fine arts gallery—is also working closely with other community leaders to see how the town can leverage what it does have to offer, which includes beautiful farmland, cultural attractions (such as the annual National Music Festival held every June), history, and education.

“One of the original missions of Washington College was to ‘educate responsible citizen leaders…’,” Massoni says. “Small towns will continue to survive due to their own citizen leaders. “We have inherited a rich legacy, we have preserved our past, and now we must embrace the future,” she says. “We must appreciate and enhance our assets, stay creative, be nimble, but also understand our limits and possibilities for growth in our little region of the world.”


The origins of Annapolis date back to the mid-1600s, and throughout the centuries, Annapolis has enjoyed the advantages that come from its harborfront location, a wealthy society, its seat as the capital of Maryland (and briefly, temporary capital of the United States), and home to both the U.S. Naval Academy and St. John’s College. With all those advantages, however, Annapolis is no different from any other city, large or small, in today’s society, according to Sean O’Neill, president of the Annapolis Business Association. Simply put, he says, “We have to adapt.” That means, among other things, embracing social media and new technology—“Those who do will do better,” O’Neill says— and thinking of creating ways to get people downtown. “Our future depends on what we as a city want to do,” O’Neill says. “We all have to be on the same page.”

The downtown district of Annapolis is unique, O’Neill says, because it has been a center of commerce for centuries. “When you walk down these streets, it’s likely that Thomas Jefferson could have been walking down the same streets,” he says. “That history lends an element of charm and romanticism that not all towns can offer.” And, of course, the attractive waterfront only enhances Annapolis’ lure for residents, business owners, and visitors.

But those same elements of charm can prove difficult when trying to keep up with the times, O’Neill says. In a town made for horse and buggies, where do you park the SUVs? And when you have an active Historic Preservation Commission, how do you renovate 18th century structures to accommodate work-space living and modern technology?

“Our aging infrastructure needs to be renovated to attract quality businesses,” O’Neill says. That being said, the downtown area does maintain high occupancy rates, both for businesses and residences.

The reason for that, says Mayor Josh Cohen, is Annapolis’ “authenticity. A mall can’t compete with a living, breathing town,” he says.

To enhance the downtown area, the city’s Main Street Program has been restarted, but is now called MainStreets Annapolis Partnership, having expanded to include not just Main Street itself, but the shopping districts of State Circle, Maryland Avenue, West Annapolis, and Eastport. The objective of the partnership, which is made up of local citizens and businesses, is to promote the customer experience, according to the mayor.

A new campaign called “Walk Annapolis” is one way to enhance that experience. “We want to emphasize Annapolis’ walkability,” Cohen says. “Downtown Annapolis is no bigger than a mall, and you have the benefit of being in a real environment.”

Cohen hopes to extend this vision by eventually enacting the Annapolis City Dock Master Plan, which calls for broad and substantial redevelopment of and improvement to the layout and structure of the waterfront cityscape. The master plan created by the City Dock Advisory Committee was revealed in December 2012, proposing gradual improvement of historic layout, scale, and vistas; balance in transportation; greening and sustainability; increasing public art; and high quality walkable public open spaces. It now awaits residential and government scrutiny before it can be implemented.

Keeping an emphasis on mobility, the city’s four parking garages are now under new management and have been modernized (until recently, patrons couldn’t even pay by credit card), cleaned, and freshly painted; on-street coin-operated meters will be replaced with those that accept credit cards; a mobile app is being developed that will let visitors know how many and where parking spaces are located; and a free circulator trolley, which began operating two years ago, is now serving almost 120,000 people a year.

“We want to make it easier for people to get around downtown,” Cohen says. “There’s more work to do, but so far, our efforts have been successful.

“The key to both the past and the future of downtown Annapolis is its uniqueness, and the personal connection it offers to both history and the people who live and work here,” Cohen says. “It’s that connection that people are yearning for.”