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.

Business Intervention, Retention and Expantion (BIRE)

Main Street Chestertown was awarded a grant in 2020 to provide business coaching to new and existing businesses to help them build, improve and grow. Led by Garrett Glover, a serial entrepreneur in the restaurant and retail industry, the program gives Chestertown businesses guidance on how to make the most of their business’s potential.


E-Commerce Support

In response to increased demand for online shopping, curbside pick-up, and contactless shopping options, Main Street Chestertown has developed workshops and coaching for downtown businesses to add or improve their website and social media. Workshops include basic e-commerce website platforms and product photography. Participants receive one-on-one coaching as needed.

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.