Sprucing Up

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.

A Cross Street building gets a fresh coat. Photo by Kevin B. Moore.


Main Street Historic Chestertown (MSHC), with funding from the Community Legacy program administered by 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 program was created to encourage building renovation, historic preservation and improved economic vitality.  It is known that 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 grants to cover up to 50 percent of the total cost of a facade improvement project, with a minimum project cost of $2,000 and a maximum grant amount of $20,000. 

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

The Façade Improvement Project is administered by a three-member panel (The Façade Improvement Grant Review Panel), volunteers with expertise in areas that include architecture, design, sustainability and preservation. Current members are Barton Ross (chair), Ellen Hurst, and Ed Minch.  


The program gives the highest consideration to projects that improve a building facade’s physical appearance and, thus, the attractiveness of Chestertown’s pedestrian streetscape.  We encourage applicants to go beyond basic maintenance and make noticeable improvements in the design and aesthetics of the facade when possible.  Only improvements visible from the street are eligible for funding. They include but are not limited to:

  • Reconstruction or replacement of historic features
  • Removal of inappropriate architectural elements and finishes.
  • Door and window repair, replacement, and redesign
  • Exterior painting and restoring finishes and materials
  • Awnings
  • Decorative and functional exterior lighting
  • Masonry and siding repairs
  • Signage
  • Gutters and downspouts


The Main Street program focuses on the revitalization of the historic downtown commercial district and operates within the boundaries of the 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, with some notable exceptions: According to conditions set in our funding agreement with the State, we cannot approve grants to active religious institutions, pawn shops, gun shops, tanning salons, massage parlors, adult video/book shop, adult entertainment facilities, check-cashing facilities, gambling facilities, tattoo parlors or liquor stores.


Preference will be given to projects that will restore a building’s historical integrity, that improve the exterior appearance of a retail store or restaurant, and that involve coordinated efforts of contiguous properties. The Façade Improvement Grant Review Panel also will favor projects that include professional design expertise from an architect and/or designer.

Applicants must own commercial property or a business located within Chestertown’s Main Street District (the Historic District). If a business is leasing its space, it must obtain 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 will be happy to meet with you to discuss the potential changes/renovations that will provide the greatest impact in terms of aesthetic appeal.   To schedule a meeting,  email or call Kay MacIntosh, manager of the Main Street Historic Chestertown program (410-778-2991, kay.chestertown@gmail.com).

Applicants can pick up the application form at Town Hall, 118 N. Cross Street, or download it HERE.  Click HERE for a copy of the guidelines. There is no annual deadline for applications; applications will be considered in the order they are received and grants will be awarded until Main Street’s funding from the Department of Housing and Community Development is depleted.

Applicants will submit:

  1. The two-page application.
  2. Two or more color photographs of the building exterior.
  3. Detailed drawings and/or written specifications of the proposed renovations/improvements, with material samples, paint colors, etc.
  4. Two or more bids on contractor letterhead.


Within 30 days of receiving the application, the Façade Improvement Review Panel, will make a decision to a) approve b) reject or c) suggest revisions to the proposed changes.

Once an applicant’s plan is approved and the Main Street Chestertown Board of Directors has voted to authorize the grant, the Façade Improvement Review Panel will forward the application to the Maryland Historic Trust for its review, as required by the State. The Trust typically  renders its review within 30 days.

While awaiting the review by the Trust, the applicant should submit the plans to Chestertown’s Historic District Commission, which will ensure that all project materials and designs meet the standards for the District. Any revisions required by the Commission should be forwarded to the Façade Improvement Review Panel.

When the Maryland Historic Trust and the local Historic District Commission have both granted their approval, Main Street Chestertown will contact the applicant and 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.

To qualify for reimbursement, renovation 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.