Soul Café: a WIN for everyone By Lisa J. Gotto

Just one of the things we love about Chestertown is our small business community. We love to frequent and support our local shops, restaurants, and service providers whenever we can, and we certainly love when we hear about a new business opening up.

As part of our recent travels in and around town we stumbled upon a sweet, new little spot called The Soul Café. Perhaps, you have yet to hear about the Café, but before you start asking how good and affordable the food is, we have to tell you it’s more of a BYO-type place, and it isn’t exactly new.

More of a traditional concept with a new twist, the Soul Café is located in a place that you’d least expect, tucked into about 230 square feet of the existing 10,000 square-feet of display space of the Women in Need Vintage & Thrift store at 106 Philosopher’s Terrace—a store and a community stalwart celebrating 25 years in operation in 2025

The Café, which has actually been open for well over a year now, is in-part the brain child of the thrift store’s director, Karen Dionisio. Designed initially to be a space for local artisans and craftspeople to display and sell their offerings within the confines of the greater thrift store, Dionisio fleshed the concept out further, added a donations-encouraged coffee bar and enhanced the space with some cozy little seating areas and curtains. With a lot of ingenuity and some existing (and charming) donated goods and furnishings, Dionisio created a place where “thrifters” can take a break from shopping and neighbors can sit and chat a bit when they inevitably run into one another there.

What is novel, is the concept of converting some of a thrift store’s square footage into a multi-use community gathering space that, Dionisio says, is attracting a respectable amount of repeat patrons. Those patrons could be among the many who support Women In Need, WIN, with their tangible donations on a regular basis, or those looking for items in the store, or basically anyone who enjoys the sense of community fostered around a cup of coffee and a space curated to encourage conversation and connection—and there has been a lot of both over the years at WIN.

It was connection that inspired Dionisio about three decades ago, to assist a friend in need who was struggling to find a way forward from an emotionally abusive marriage with little to no resources. Dionisio, who is a Chestertown native, said she was living in Virginia at the time with her young family, when she and some other friends saw their friend floundering and they all decided that they would pitch in in some way to get her back on her feet.

“We helped pay her rent, we helped find her a new place to live because she had to get out of where she was in Fairfax, Virginia, which is very expensive,” says Dionisio.

“So, it took a lot of us. There was a group of us. And to make a long story short, we carried her through her situation for about two years,” after which, Dionisio adds, she felt the need to come back to Chestertown to address some issues with her own family homestead. What was supposed to be just a temporary stay, turned into a much bigger mission.

It turned out that Dionisio’s friend would also relocate to Chestertown, and in doing so, would 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 like her that we needed to provide that kind of support and resources to. That’s really what started it, and so then we incorporated Women in Need,” explains Dionisio.

Many from the original group who assisted Dionisio would relocate to Chestertown, as well, and would play an integral role in the formation of the 501 C3 nonprofit as board members.

“They all loved it over here, so they relocated, which was great, because that made it much easier for us as board members to meet and to plan,” says Dionisio.

Those plans included assessing what the greatest needs in our local, rural area were. From those assessments several of the concern’s first programs were developed. One would address the issues that living and getting around in a widely rural area present if you don’t have access to an automobile.

In that first effort, Dionisio says, they received four or five donated vehicles.

“We provided the insurance, we kept them on the road, we lent them out to the women who were living outside of town who needed them to get their kids to school or needed them to get to jobs.

“And then we began to look at housing. We wanted to have a home where people could transition,” Dionisio explains. They wanted to ensure that access to a roof overhead was always available at least in the short-term so women could transition back to safer lives where they can start building agency for themselves and their children; lives where they would have access to the key things that everyone needs to perform life’s most basic, but necessary functions.

The programs that WIN was able to establish at that time would help people pay their rent, utilities and even prescription medication, when necessary. One of the ways they raised money to fund these programs was to hold a silent auction. Dionisio recalls a responsive community who were willing help make the auction a success.

“People donated a bunch of stuff to this silent auction.” It was from this effort, Dionisio says, they realized the funds that could be raised from goods liquidation, and they had so 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 so they could house and sell the goods they collected for the good of others in the community.

And so began the relationship between that 10,000 square-foot storefront on Philosopher’s Terrace, the Women in Need organization, and the community at-large.

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 what WIN’s mission is, 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 on many levels and with many people throughout the area.

“Karen helps out on the periphery, as well,” Caswell continues, pointing to the subtle ways the organization supplements their mission by working with other businesses and organizations throughout the community to address needs.

“For example, if the theatre is doing something at the Garfield or the high school, and they need props or furniture, Karen is more than willing to lend anything that she has in her inventory.”

Caswell relays that while she often shops the store for fabrics for the quilting and crafting she does, she sees the experience of shopping there as something much more, and she has also donated her own time to assist WIN with special projects and events.

“It’s that small-town awareness, liaisons, and comradery that happens in a community like Chestertown.”

And it is that sense of comradery that encouraged Dionisio to want to create The Soul Café, which she hopes will become that great little spot where small local groups can gather, grandmas can compare their WIN “finds” and where good friends can just sit and share a moment, a smile, and a cup of coffee.

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.

Lisa J. Gotto has written for What’s Up Annapolis, Star Democrat, and Kent County News, among other publications.