Main Street Recovery Grants

Main Street Historic Chestertown
Main Street Recovery Grants
for COVID Relief and Innovation


Main Street Historic Chestertown is offering grants of $1,000 to $10,000 for downtown Chestertown businesses affected by the pandemic. The grants are intended to provide relief for COVID-19 losses as well as help with the cost of adaptive strategies and innovations.  Please see the guidelines below and the link to the online application. The application portal will be open for ten days, from Friday, Feb. 5 through Monday, Feb. 15.

Please note: The application form will not allow you to save information before you submit, so please have all information ready before you begin. To download a preview of the questions, click here or email



To be eligible for the recovery grant program, a business must:


  1. Have a physical location in the Main Street District, which operates with the same boundaries set for the Chestertown Historic District (see map here).
  2. Be a registered business in good standing with the State of Maryland and the Town of Chestertown.
  3. Have no more than 25 employees.
  4. Be a for-profit retail, restaurant, personal- or professional-service business. Nonprofits, medical practices and home-based businesses are not eligible.



  • Commercial mortgage, rent and utility bills
  • Payroll
  • Resources to establish or enhance online sales and marketing functions
  • Special expenses related to COVID-19 services, adaptations or innovations (such as patio heaters, tents, HVAC upgrades, technology and online sales upgrades, etc.) not covered by previous federal, state, or county grants
  • Working capital for inventory
  • Fixtures, furnishings and equipment for improved merchandising and customer experience

Successful applicants will be required to spend grant funds within three months and will be required to show proof of the expenditures, i.e. receipts, invoices, product shots, etc.



Applications will be accepted on the Main Street Chestertown website from 9 a.m. Friday, February 5 through 5 p.m. Monday, February 15.

Applications will be reviewed by a subcommittee made up of representatives from the Main Street Chestertown Board of Directors and volunteer mentors from the local chapter of SCORE. Board members who own or are employed by a business that applies for a grant must recuse themselves from all aspects of the review and award process.



Criteria for selecting grantees and setting grant amounts will be based on the perceived impact  the funding will have on the business and the perceived impact the business has on the local quality of life and the visitor experience. Because of limited funding, not every applicant will receive a grant.

Strong candidates for larger grants will be those businesses that are open more hours, will retain more jobs, fill a consumer need or niche, and exhibit the ability to pivot, innovate and adapt to changing circumstances.

Questions? Contact



Download pdf of guidelines HERE.