The Chestertown Chat
Stories, events and news from downtown Chestertown, written by the people who live, work and shop here.
‘The Great Scrooge Off’ and Ghost Scavenger Hunts Top New Additions to Chestertown’s Annual Dickens of a Christmas Festival
Downtown transforms into 1840s London Dec. 4–5 for the historic town’s most immersive holiday weekend yet. Main Street Chestertown is proud to announce Urgo & Associates at 98 Cannon St. […] Read More
Main Street Chestertown Invites Applicants for Board of Directors
Main Street Historic Chestertown is inviting civic-minded community members to apply for open seats on its Board of Directors. As a 501(c)(3) non-profit organization partnering with the town and Kent County, Main Street Chestertown is dedicated to preserving,…
Spooky Season Arrives in Downtown Chestertown
Black Cat Art Trails, Scarecrows, Cult Classic Theater, and Tall Ships Pack the pre-Halloween Season.
$1 Rides and High Usage Mark Milestone First Year for Chestertown Community Bike Share
Marking a major milestone for local transportation, downtown vibrancy, and town connectivity, Main Street Chestertown is celebrating the one-year anniversary of its community Bike Share Program. Launched in September 2025 in partnership with the Town of Chestertown…
Bespoke Chocolate Opens With New Renovations
Things just got a whole lot sweeter in Downtown Chestertown! Bespoke Chocolate has officially opened the doors to its new, expanded location at 103 S. Cross Street, marking an exciting new chapter for the beloved local business. The move and transformation were made…
Robin Sesplankis, Dedicated Public Servant, Named Visitors Center Manager
ongtime staff member Robin Sesplankis has been promoted to Manager of the Kent County Visitors Center. Known for her memorable travel advice and warm hospitality, Robin steps into the role as the Center prepares to surpass 2025 visitation numbers, having already welcomed over 2,000 global travelers this year.
National Recognition and Waterfront Planters Showcase the Collective Spirit Keeping Chestertown Vibrant
This week, Main Street Chestertown is celebrating the collective spirit – from organizational leadership all the way to the hands-on dedication of individual neighbors – that keeps our historic downtown thriving. We’re pleased to announce we have again…
Main Street Chestertown Welcomes New Executive Director, Dominique Ellis Falcon
Main Street Historic Chestertown is thrilled to announce the appointment of Dominique Ellis Falcon as its new Executive Director. With a 20-year career spanning tourism marketing, coalition building, operational leadership, strategic communications, and community…
A Day Trip to Chestertown for Culture, Cuisine & Cocktails
Chestertown, Maryland is the kind of Eastern Shore town that rewards a slow wander. Spend the day exploring coffee shops, bookstores, galleries, Chesapeake history, waterfront views, cocktails, oysters, and live theater.
Growing Toward the Future: Opportunities to Upgrade and Invest in Your Downtown Business
Chestertown’s downtown businesses have new opportunities to invest in their future. From Enterprise Zone tax incentives to Facade Improvement Grants, local business owners and property owners may be able to access funding and support for upgrades, renovations, and long-term growth.
Main Street Chestertown Earns National Accreditation For Excellence in Revitalization
Main Street Chestertown has once again been nationally accredited by Main Street America™ for excellence in downtown revitalization. This top-tier recognition celebrates local leadership, historic preservation, and sustainable community development in Chestertown’s historic district.
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