Current Main Street Chestertown Projects

Facade Improvement Project

Main Street secures money from the Maryland Department of Housing & Community Development to sub-grant to business owners for commercial building facade improvements. All work is approved locally and by the Maryland Historic Trust. For more information and examples of past projects, visit our Facade Improvement page by clicking on the picture.

Facade Lighting Project

Similar to our Facade Improvement Project, this program works with business owners in the downtown commercial district to install historically appropriate light fixtures and lamping that create a cohesive pedestrian lighting scene. These additional lights will light walkways and sidewalks for increased safety and security. For more information, visit our Facade Lighting page by clicking on the picture.

Wayfinding Signage

Many visitors travel to our community and we want them to find all of the treasures that we love. To help them get around our town, Main Street is installing sign posts that point toward key locations such as the waterfront, Visitors' Center, and parking.

Security Enhancements

To keep all visitors safe and secure, Main Street has secured funding for additional exterior security cameras and upgraded police station monitoring systems. This equipment will assist the police in keeping our more remote areas of town (Rails to Trails, Wilmer Park, etc) safe for everyone to use.


Main Street works in conjunction with the Town, the Garden Club, the Tree Committee, the Recreation Committee, and others to keep our sidewalks and green spaces beautiful. Recent projects include rolling planters, landscaping at the African-American slavery plaque, and clean up of tree wells. We're always looking for helping hands!

Business Consulting Program

The B.I.R.E. (Business Innovation, Retention, and Expansion) Program is funded by Main Street. This program provides business mentoring services to our local businesses from a consultant from the University of Maryland Small Business Development Center.