STAY UP TO DATE
The Chestertown Chat
Downtown Master Plan Release
Press Release March 25, 2024 Main Street Chestertown and local partners are embarking on a Downtown Master Plan with Design Collective, Inc., a Baltimore-based consulting firm, to envision the future of Chestertown’s Historic District. Working in...
Explore Chestertown’s Outdoor Sculpture Tour
Public art is set to transform Chestertown, with sculptures soon to grace every corner of our historic town. Anchored by the extraordinary Woicke Collection of 24 contemporary sculptures, generously donated to the community, Chestertown's public...
A Beacon of Faith: The History of Emmanuel Church
Emmanuel Episcopal Church stands as a timeless testament to faith, community, and history. Established in 1692, just years after the founding of the town itself, Emmanuel Church has been a cornerstone of the Chestertown community for over three...
Chestertown Tea Party Celebrates 250 Years of Resilience
In May 1774, a group of courageous patriots in Chestertown, Maryland, took a stand against British tyranny and sparked a movement that would change the course of history. This year marks the 250th anniversary of the Chestertown Tea Party, a pivotal...
A Guide to Chestertown Farmers & Artisans Market
Nestled in the heart of historic Chestertown, Maryland, the Chestertown Farmers Market is a vibrant gathering place where locals and visitors alike can experience the best of the Eastern Shore's agricultural bounty. From fresh produce and locally...
Get Married in Chestertown
A Guide to Getting Married in Maryland's Historic Gem Nestled along the banks of the Chester River, Chestertown, Maryland, exudes historic charm and timeless beauty, making it the perfect setting for a romantic wedding. From its quaint streets...
Discover the Charm of First Fridays 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...
Facade Improvement Grant Program
The Spring 2024 application period will open March 1, 2024. The due date for applications will be March 31, 2024. For more information or an application, please contact the Main Street office. ABOUT THE PROGRAM Main Street Historic...
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...