
From left to right, store associate, Sondra Mack, Admin, Cheryl Hurt, and WIN’s director Karen Dionisio
Among Chestertown’s longest-running businesses, you will find the Women in Need Vintage & Thrift Store, or, WIN, in a popular, little shopping plaza just off the town’s main thoroughfare, Washington Avenue. This year, the community-based enterprise celebrates 25 years in operation; one that appropriately began with recycled treasures and has become a treasure and a source of hope and goodwill itself.
The thrift store is the brainchild of its director, Karen Dionisio, a native of Chestertown. For Dionisio, there was a sense of purpose when about three decades ago she recognized a friend was struggling to find a way forward from an emotionally abusive marriage with little to no resources. Dionisio rallied her friend group to help the woman get back on her feet.
“We carried her through her situation for about two years,” after which, Dionisio adds, she felt the need to address some issues with her own family homestead. Doing so shed light on the larger issue of women who are at-risk and low on opportunities when leaving untenable relationships.
“We recognized that this was a ministry basically, that there were many women that needed to support and resources. That’s really what started it, so we incorporated Women in Need,” Dionisio explains. Many from the original group would play an integral role in the formation of the 501 C3 nonprofit as board members.
The nonprofit then went to work assessing needs within their primarily rural community. And as the story goes, one good deed led to another. WIN would create programs to assist women with all facets necessary for building new lives for themselves and their children, including basic transportation and housing matters, would help people pay their rent, utilities, and even prescription medication.
One of the ways they raised money to fund their efforts was to hold a silent auction. Dionisio recalls a responsive community willing to help make the auction a success. It was from this effort, Dionisio says, they realized funds could be raised from goods liquidation. With much to liquidate at that time, they asked the landlord of their present space, which was sitting empty at that time, if he would consider letting them use it for just a few weeks to sell their surplus goods.
And so began the relationship between the 10,000 square-foot storefront, Women in Need, and the community. WIN was able to officially begin renting the space in 2000, and it has been a beehive of community-supported activity ever since.
“I have been patronizing the store ever since it opened,” says long-time Chestertown resident, Sue Caswell.
“I’ve always been committed to recycling and re-using, and that piece of WIN’s mission struck a responsive chord, and I am also very committed to any woman who has encountered challenges, and could use a hand in meeting those challenges in a variety of ways.”
Beyond the obvious give-and-take going on at the store, Caswell says, she also appreciates how involved Dionisio, and her organization have been within the community at-large.
“Karen helps out on the periphery, as well,” Caswell continues, pointing to the subtle ways the organization also works with other businesses and organizations, such as the local theater and high school, among many others, to address needs.
More recently, Dionisio partnered to create a multi-use community gathering space using some of the thrift store square footage. Her intention was to create a fun little spot where local groups can gather, grandmas can compare their WIN vintage “finds,” and where good friends can just sit and share a moment, a smile, and perhaps, a cup of coffee.

The Soul Café
Her effort, dubbed The Soul Café, has provided a place for local artisans and craftspeople to showcase and sell their offerings. With a lot of ingenuity and some well-curated donated goods and furnishings, Dionisio created a place where “thrifters” can take a break from shopping, and neighbors can sit and chat around the donations-encouraged coffee bar, when they inevitably run into one another at the store.
This novel gathering concept, Dionisio says, is attracting a respectable amount of repeat patrons. Those patrons are among the many who regularly support Women In Need with their tangible donations, or those looking for items in the store, or basically anyone who just enjoys the sense of community fostered there.
When asked what her favorite “find” at WIN has been over the years, Caswell posited, “You mean besides friendship?”
And a better find we do not know.
To learn more about all the ways WIN works within the community, visit win-foundation.org. Store hours are Thursday & Friday, 10 a.m. to 6 p.m., and Saturdays, 10 a.m. to 4 p.m.