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Companion Cities: Chestertown

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,...

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Downtown Master Plan Release

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...

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Explore Chestertown’s Outdoor Sculpture Tour

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...

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A Beacon of Faith: The History of Emmanuel Church

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...

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Chestertown Tea Party Celebrates 250 Years of Resilience

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...

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A Guide to Chestertown Farmers & Artisans Market

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...

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Get Married in Chestertown

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...

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Facade Improvement Grant Program

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...

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5 Things to Do in May in Chestertown

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...

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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...

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How to get involved in Main Street Chestertown

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...

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Top Five Reasons to Shop Small

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:...

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Why Should You Become a Corporate Sponsor?

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...

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