Economic Vitality


Façade Improvement Program

With funding from the State Department of Housing and Community Development, Main Street Chestertown is offering 50/50 matching grants up to $20,000 for facade improvements.  Click for more info.

GCI Revolving Loan Program

Also known as the “Open for Business in Chestertown” program, the Greater Chestertown Initiative Revolving Loan Fund was established by the GCI, a local networking organization, and SFW Foundation to aid economic development in Chestertown.

It provides financial assistance through matching funds and interest-free loans to eligible individuals/businesses looking to start a new business, expand or relocate operations to Chestertown. Residency in the town is not required of the business owner(s); however, the business must be physically located in Chestertown. Download a packet about the program here.

Businesses of Chestertown: Cat Colloquium

By Ellen Uzelac Heard about Cat Colloquium, High Street’s new happy place? If you haven’t, you will. First, what it’s not. Cat Colloquium is not a cat café or a cat shelter. It’s a playful, whimsical space designed to support the community’s well-being – in [...]

Hegland Glass

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

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 [...]

Chestertown RiverArts

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

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 [...]

Erin Heckles – Twigs & Teacups

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

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

  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 [...]

Listening Room

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 Artist’s Gallery

            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 [...]

Ingrid Hansen – Figg’s Ordinary

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 & John Laucik – Chester River Wine and Cheese Co. and Welcome Home

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 [...]

Bob Ramsey – The Finishing Touch

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 [...]

Joyce Hale – Gabriel’s

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 – The Bookplate

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, [...]

Robbi Behr and Matthew Swanson – Idiots Books

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 [...]

Jaye Owings – Flow Salonspa

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 [...]

Carla Massoni – Massoni Gallery

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 [...]

Doug Rae – Evergrain

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 [...]

Resources for Doing Business in Chestertown

Downtown Chestertown Association (DCA)

is a non-profit, member-based organization that promotes businesses and professional services in and around Chestertown through activities that encourage residents and tourists to visit and shop locally. It also organizes and promotes numerous popular events such as First Fridays, Taste of the Town, Crazy Days, and Holiday Celebrations.


Kent County Office of Economic Development 

This county office is a valuable resource for those interested in opening or expanding a business in the county, including the county seat of Chestertown. It collaborates with state and regional programs of interest to business owners.
Contact: Ms. Jamie Williams, Economic Development Coordinator, at 410-810-2168, or


Maryland Business Lending Programs, Community Development Administration

Part of the Maryland Department of Housing and Community Development, this agency offers low interest loans to start or grow businesses in the state. Contact: Mr. Cheivelle Hill at or 301-429-7518


Upper Shore SCORE

The local chapter of this national organization offers business advice and counsel from retired business executives, free of charge. The offices are located at 122 North Cross Street, Chestertown, MD 21620. Telephone (410) 810-2969.


Maryland Small Business Development Center 

This partnership between the U.S. Small Business Administration and the University of Maryland has an Eastern Region Headquarters at Salisbury University and an office at nearby Chesapeake College in Wye Mills. To learn about its free consulting for new or existing business ventures, contact Regional Director John Hickman at , 410-546-33679; consultant Richard Loeffler,; or office manager Karin Spignolo, 410-827-5304.