A view of downtown Chestertown on High St. featuring the new facade at Flow Salon in Spring 2026

Growing Toward the Future: Opportunities to Upgrade and Invest in Your Downtown Business

Give your business a glow up! Chestertown’s downtown businesses have some exciting opportunities to invest in their spaces, strengthen their operations, and position themselves for long-term success. 

With Kent County’s recent renewal of the Chestertown Enterprise Zone and Main Street Chestertown’s ongoing Façade Improvement Grant Program, downtown Chestertown property owners and business operators have even more tools to support meaningful reinvestment in downtown.

Whether you’re refreshing your storefront, renovating a commercial property, expanding your business footprint, hiring new employees, or planning long-term capital improvements, now is an excellent time to explore what incentives are available.

Enterprise Zone Renewal: Incentives for Growth

Kent County has officially renewed the Chestertown Enterprise Zone designation for another ten years, preserving access to a powerful state-backed economic development incentive for eligible businesses and property owners. The program is intended to encourage reinvestment, support expansion, and help local businesses remain competitive as they grow. Businesses located within the designated zone may qualify for real property and state income tax credits tied to capital investment and job creation. 

If you are planning a renovation, expanding operations, or hiring new staff, the Enterprise Zone may help offset those costs.

Façade Improvement Grants: Invest in Your Storefront

For businesses located within Chestertown’s Historic District, Main Street Chestertown’s Façade Improvement Grant Program offers another way to invest in your property’s appearance and curb appeal.

Eligible applicants may receive up to 50% matching funds toward façade improvement costs, including a 100% match on the first $1,000 of eligible improvements, with grants ranging from $2,000 to $20,000 depending on project scope and funding availability.

Improvements may include exterior restoration, storefront enhancements, signage, paint, windows, lighting, and other approved façade upgrades. Projects must be approved before work begins.

Get Started

Not sure where to start? Main Street Chestertown is happy to help guide you through the process. For more information, please contact director@mainstreetchestertown.org

Businesses and property owners interested in either program should begin by confirming eligibility and discussing project plans with the appropriate administrators:

Enterprise Zone Program |  Kent County Department of Economic and Tourism Development: https://bit.ly/4mzAm3Z

Façade Improvement Grants | Main Street Chestertown: /facade

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Chestertown, Maryland was founded in 1706. It was established as a port town and played a significant role in the colonial era, serving as a bustling trade hub along the Chester River. Today, Chestertown retains much of its historic charm and is known for its well-preserved 18th-century architecture and vibrant cultural scene. Thanks for checking us out!

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