Hegland Glass This spring, Hegland Glass celebrates 10 years in business and 8 years as fixtures in downtown Chestertown. Leaving behind corporate careers, Dave and Patti Hegland turned their attention to creating contemporary kiln-formed art glass. In the decade since then, they've made a name [...]

Music Life and owner Bill Drazga have been fixtures in downtown Chestertown for more than seven years. When you step inside, you can see all kinds of musical instruments, from acoustic and electric guitars, to pianos, to band instruments. Not only can you find an [...]

Maria Wood - Chestertown RiverArts A conversation with Chestertown RiverArts new Executive Director, Maria Wood Chestertown RiverArts is one of the vibrant nonprofits that helps keep our community lively and fun. Known for First Friday receptions and gallery exhibits, the Recycled Runway, and the Clay [...]

Tiny Tots Boutique When Sharon Puckett and Dale Hornstein moved to Chestertown a few years ago, she noticed that there wasn't a children's clothing store. A grandmother herself, she decided to open a shop to carry the kinds of clothing and gifts she would want [...]

Twigs and Teacups has been a fixture of Downtown Chestertown since 1991 with its current owner Erin Heckles at the helm since 2014. Being part of the close-knit community downtown and having a good relationship with other shop owners is part of what Erin loves [...]

CHESTERTOWN ELECTRIC Part retail shop, part museum, Chestertown Electric has made a name locally and regionally as the go-to for rare, vintage and historical light and fan fixes and finds. Owner David Hoatson is an electrical engineer with more than 40 years experience in defense [...]

  Bee Crafty Collectibles is celebrating its third anniversary as a member of the Chestertown Main Street community on Friday, November 29! Owner Helen Cowley, invites you to celebrate her anniversary with a special sale, giveaways, and a chance auction. This little shop is filled with [...]

Housed in a charming wood frame house, "The Listening Room" audio store has something for both the casual listener and the serious audiophile. Whether you're looking for the latest "High and Wides" album or a top-of-the-line sound system, owner Michael Hoatson is ready to fill [...]

            The Artists' Gallery is a partnership of Evie Baskin, Bonnie Howell, Mary Ellen Mabe, Nancy R. Thomas, and Barbara Zuehlke. All of the artsist/owners are talented artists themselves and come from throughout the region. The gallery first opened 15 years ago and [...]

Photo by Lorentz Hansen     Figg's Ordinary began in 2015 as a small stand in the Chestertown Farmers' Market. Figg’s founder Ingrid Hansen began experimenting with gluten-free baking after her youngest daughter developed a sensitivity to gluten and struggled to find gluten-free products that were [...]

Robert Ortiz has been making fine furniture for over 30 years, 20 of those years right here in downtown Chestertown. Bob has created his own unique style, combining elements of the Japanese and Shaker woodworking traditions. He uses exquisite woods, that he hand-selects with his [...]

Jennifer Baker and John Laucik opened Chester River Wine and Cheese Company on Cross Street in 2015. Former corporate management consultants turned “everyman foodies,” they had left the rat race in Philadelphia behind for a life in Chestertown selling fine cheeses, charcuterie, and other gourmet [...]

Starting in 1978, when he was fresh out of college, Bob Ramsey has offered custom framing, fine art, artist’s materials, and select gifts on High Street in his hometown of Chestertown. He has framed everything from patchwork quilts to oil paintings, and today’s clients can [...]

In 2010, Joyce Hale built on the success of her clothing and gift shop in Galena, Maryland, and opened up a second location in downtown Chestertown. Offering an eclectic mix of items from scarves and jewelry to home décor, children’s toys, and party goods, Hale [...]

Tom Martin’s shop on Cross Street, full of new-to-you hardcover and paperback books across a wide range of categories, is an excellent place to browse for a new beach read or a collectible first-edition printing of Beautiful Swimmers. The Bookplate’s inventory also covers world history, [...]

In 2006, Robbi Behr, an illustrator, and her husband, writer Matthew Swanson, moved to Behr’s hometown of Chestertown to begin a small press. Named Idiot’s Books, Behr and Swanson created illustrated picture books for adults out of a barn in the Historic District. Their success [...]

Since 2009, Kent County native Jaye Owings has been fulfilling her passion for beauty and conservation at Flow Salonspa, where she and her talented team of stylists, spa therapists and nail therapists offer a holistic approach to wellness. An Aveda salon, Flow demonstrates a commitment [...]

For more than 25 years, Massoni Gallery has been a cornerstone of Downtown Chestertown’s art scene. Gallerist Carla Massoni curates a sophisticated blend of work by locally based, nationally renowned artists such as Marc Castelli, Greg Mort, Marcy Dunn Ramsey, and Vicco von Voss. Her [...]

Founded in 2011, Evergrain is a bakery and coffee shop established and operated by head baker and owner, Douglas Rae. A trained graduate of Johnson and Wales University, Rae returned to his hometown of Chestertown to put down roots in a business that would both [...]