Giving Tuesday


Thank you for giving to Main Street Chestertown! Your gift will help us foster an inviting, diverse and prosperous downtown.

Chestertown is a great place to live, work and play, and Main Street strives to support and enhance the qualities that make it welcoming and vibrant. Over the past three years we have secured nearly $400,000 in state, federal and foundation grants for downtown projects.

Here are just a few of the projects that Main Street has underway to support a thriving and growing community:

  • Annual visitors map and event calendar.
  • Façade-improvement program offering grants of up to $20,000 to property owners and their tenants.
  • New events to bring residents and visitors downtown
  • Dickens of a Christmas Festival, now in its third year of lively Victorian entertainment, food and shopping.
  • Monthly Cars on High gatherings for auto enthusiasts and an annual Chestertown Car Show.
  • Spring Bluegrass Block Party
  • The design and manufacture of wayfinding signage for visitors. Coming summer 2020!
  • The purchase of a mobile stage for Town and nonprofit events. Coming spring 2020!
  • Intensive business consulting program for local businesses interested in creating a more dynamic shopping and dining destination downtown.
  • New planters and plantings to enhance the streetscape.

With your support we can continue to identify and pursue opportunities to enhance and invigorate downtown Chestertown. Read more about our mission, vision, and approach here.


Thank you!