STAY UP TO DATE
Chestertown News
Stay Up to Date with
Main Street Chestertown
Explore the latest stories, events, and updates from the heart of Chestertown, Maryland. Our blog highlights the vibrant culture, rich history, and community happenings that make our town unique.
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.
Kent County and Main Street Chestertown Awarded Grants to Support America’s 250th Semiquincentennial Planning
FOR IMMEDIATE RELEASE April 30, 2025 Kent County and Main Street Chestertown Awarded Grants to Support America’s 250th Semiquincentennial Planning Kent County, MD: The Kent County Department of Economic and Tourism Development and Main Street…
Main Street Chestertown Unveils Downtown Master Plan to Shape Future Growth and Revitalization
March 4th, 2025 Chestertown MD Main Street Chestertown is proud to announce the public release of its highly anticipated Downtown Master Plan Phase 1, a comprehensive vision designed to guide…
Main Street Welcomes New Executive Director, Sonia “Sonny” Huntzinger
November 4, 2024 – Chestertown, MD — Main Street Chestertown is thrilled to announce the appointment of Sonia “Sonny” Huntzinger as its new Executive Director. With over two decades of experience in economic development, tourism marketing, and…
Companion Cities: Chestertown
In case you were wondering why there is a Canadian flag flying in front of the Chestertown Maryland Town Hall…..here’s how it came to be. Since 1987 Chestertown, Maryland has been the Companion City of the municipality of the district of Chester,…
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…
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…
Stay Up to Date With Main Street by Joining Our Monthly Newsletter!
Newsletter Archive
Upcoming Events
Interested in upcoming events in Chestertown, MD? Make sure to check out our Calendar of Events!
Support Main Street Chestertown
Your donation fuels everything from local festivals and beautification projects to business support and historic preservation.
Together, we build a stronger, more connected Chestertown—one event, one storefront, one block at a time.
Give today and make a lasting impact.