Sprucing Up

Painting A Cross Street Facade.Crop.KevinMoore

Main Street Chestertown Facade Improvement Grants 

Commercial building owners and their tenants in the Historic District can apply for up to $20,000 in matching grants to improve the look and integrity of their facades.

About the Façade Improvement Program

Main Street Historic Chestertown, with funding from the Community Legacy Program administered by the State of Maryland’s Department of Housing and Community Development, offers matching grants for façade improvements made to commercial buildings and storefronts in the historic downtown district. The Façade Improvement Program was created to encourage building renovation, historic preservation, and improved economic vitality. Quality aesthetics increase property values and sales revenues, improve the marketability of space within the buildings, and draw businesses and residents to the area.

Main Street Chestertown currently offers matching grants to cover up to 50 percent of the total cost of a facade improvement project, with a minimum grant amount of $1,000 and a maximum grant amount of $20,000.

NOTE: Work completed prior to a letter of commitment is not eligible for funding.

The Façade Improvement Program is overseen by a five-member review panel (the Review Panel), a group of volunteers with expertise in areas that include architecture, design, and preservation.   Main Street’s Executive Director is the staff administrator.

Who Can Apply?

Main Street’s Façade Improvement Program focuses on the revitalization of the historic downtown commercial district within the boundaries of the Chestertown Historic District.

Any owner of a commercial building in the Historic District, or a store owner/tenant of a commercial building in the District who has obtained the required authorization from the property owner, can apply for funding.

Highest priority is currently directed to commercial buildings on the following blocks:  200 and 300 blocks of High Street, 100 and 200 blocks of South Cross Street, 200 and 300 blocks of Cannon Street, and Park Row.

What Kind of Work Is Covered?

The Façade Improvement Program gives the greatest consideration to projects that significantly improve a building’s physical appearance and, thus, the attractiveness of Chestertown’s pedestrian streetscape.  Preference will be given to projects that will restore a building’s historical integrity, that will improve the exterior appearance of a retail store or restaurant, and that will involve coordinated efforts of contiguous properties. The Façade Improvement Program encourages projects to include professional design expertise from an architect and/or designer. Only improvements to the sides of the building that face the street or a public thoroughfare are eligible for funding.

Applicants must go beyond basic maintenance and make noticeable improvements in the design and aesthetics of their façades.  Such improvements include but are not limited to:

  • Awnings, window boxes, and planters
  • Door and window replacement and redesign
  • Restoration of finishes and materials
  • Decorative and functional exterior lighting
  • Masonry and siding
  • Signage
  • Reconstruction or replacement of historic features
  • Removal of inappropriate architectural elements and finishes.

Additional Guidelines

Applicants must own the commercial property specified on the application or be a business that leases space in the building and obtains the required authorization from the building owner as part of the application process.

Reimbursements will be based on actual project costs, not including in-kind labor or donated materials.

Want a pre-application conversation? Members of the Review Panel are willing to meet with interested property/business owners to discuss potential changes/renovations that will provide the greatest impact in terms of aesthetic appeal. To schedule a meeting, email manager@mainstreetchestertown.org or call the Main Street office at (410) 778-2991.


The application can be downloaded HERE.  Click HERE for a copy of the guidelines. Alternatively, the application can be obtained from Main Street’s Executive Director by email (manager@mainstreetchestertown.org) or at the Main Street office on the second floor of Town Hall, 118 N. Cross Street.

Applicants must submit:

  • The two-page application;
  • Two or more color photographs of the building exterior;
  • Detailed drawings of the proposed renovations/improvements; and.
  • Two or more bids on contractor letterhead.



The Facade Improvement Program is operated on a rolling applications basis. That being said, the Review Panel usually meets, as needed, on the last Thursday of each month. Applications must be received by end of day on the Friday prior to the meeting date to be considered at that meeting.

Within 30 days of receiving the application, the Review Panel will make every effort to have a recommendation to:  a) approve; b) reject; or c) suggest revisions to the proposed renovations.

The Review Panel forwards its recommendations to the Main Street Board of Directors for its review.  If approved by the Board, the application is then sent to the Department of Housing and Community Development, which in turn forwards it to the Maryland Historical Trust for its review as needed. The State agencies typically render their reviews within 5 to 30 days; the longer period applies to historically significant properties.

All applications must also be approved by the Chestertown Historic District Commission (HDC), which will ensure that all project materials and designs meet the standards for the Historic District. Applicants are encouraged to submit their plans to the HDC for review simultaneously with their submission to Main Street. HDC applications are available from Town Hall staff and online at TownofChestertown.com. HDC decisions must be promptly reported to Main Street’s Executive Director.

When the State agencies have all granted their approvals, Main Street will issue a letter of commitment for the project, including the amount of the grant and any conditions of approval.

The applicant will be responsible for obtaining all the necessary building and work permits for the project and for conforming to applicable safety standards.

Façade Improvement Program projects must be started within six months of the time of approval and completed within one year.

Once the project has been completed, the applicant will present proof of expenses (canceled checks, paid invoices, contractor’s sworn statements, etc.) to the Main Street office for reimbursement up to the amount of the grant. To qualify for reimbursement, the work must conform to the descriptions in the approved application.

With the requirements successfully met, Main Street Chestertown issues the reimbursement check to the applicant. Once the check has been cashed, Main Street submits its own reimbursement request to the Maryland Department of Housing and Community Development.