GET UP TO DATE
BLOG
Facade Improvement Grant Program
The Fall 2023 application period will open September 1, 2023. The due date for applications will be September 30th, 2023. For more information or an application, please contact the Main Street office. ABOUT THE PROGRAM Main Street...
Transforming Chestertown: Streetscape Improvements to Enhance Charm and Vibrancy
Chestertown, Maryland, is preparing for an exciting transformation as streetscape improvements are set to enhance the town's charm and vibrancy. With a focus on revitalizing key areas, these improvements aim to create a more inviting and appealing...
5 Things to Do in May in Chestertown
In May, Chestertown, Maryland offers a range of activities and experiences to enjoy. Here are five things you can do: Attend the Chestertown Tea Party Festival: Join in the town's iconic annual event that commemorates the historic Tea Party...
Dickens of a Christmas Festival
At the Dickens of a Christmas Festival, visitors and locals alike enjoy a festive Christmas atmosphere with Dickensian performers, horse-drawn carriage rides, and musical performances. Local shops, restaurants, and businesses host special holiday...
How to get involved in Main Street Chestertown
There are a variety of ways to get involved with Main Street Chestertown. You can volunteer to help with clean-ups, community events, or join one of the many Main Street Chestertown committees. Additionally, you can attend special events, like art...
Top Five Reasons to Shop Small
1. Supporting Local Businesses: Shopping small helps to support local businesses and the economy of a community. By shopping small, you are helping to keep money local and stimulate the economy of the area. 2. Personalized Shopping Experience:...
Why Should You Become a Corporate Sponsor?
As a corporate sponsor, you have the opportunity to create a lasting connection with your target audience. You can use your sponsorship to reach new customers and build brand awareness. Corporate sponsors also have the ability to leverage their...
First Friday’s in Downtown Chestertown
First Friday in Chestertown is a monthly event that celebrates the town's vibrant arts and culture. Held the first Friday of each month, First Friday is an evening of music, art, food, and fun in downtown Chestertown. Local businesses and...
PLAN YOUR VISIT
FREQUENTLY ASKED QUESTIONS
Curious about frequently asked questions like "Where to park?" and "What time does First Friday start?" Click here to find all the answers you need in our comprehensive FAQ section.
UNLOCK THE CHARM OF CHESTERTOWN
Discover the insider knowledge on where to find the best cream of crab soup in town, indulge in the tastiest ice cream, and plan your visit to the art galleries. Let us guide you to create a spectacular experience in Chestertown that combines culinary delights, sweet treats, and a journey through the town's vibrant art scene.
DOWNLOAD WALKING MAP
Chestertown, Maryland was founded in 1706. It was established as a port town and played a significant role in the colonial era, serving as a bustling trade hub along the Chester River. Today, Chestertown retains much of its historic charm and is known for its well-preserved 18th-century architecture and vibrant cultural scene. Thanks for checking us out!
office@mainstreetchestertown.org
PHONE
(410) 778-2991
OFFICE
Chestertown Town Hall
118 N. Cross Street
Chestertown MD 21620
MAILING ADDRESS
PO Box 427
Chestertown MD 21620
Main Street Chestertown would not be possible without the support of our partners:
