2026 Facade Improvement Grant Applications Now Open!
Chestertown, Maryland
Eastern Shore Life At Its Best
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Rich in History.
Rooted in Community.
Voted The Best Small Town in Maryland to Chill Out
Immerse yourself in our rich history as you stroll down brick-lined streets, lined with 18th-century homes and historic landmarks. Explore our bustling arts scene, with galleries and studios showcasing local talent. Indulge in fresh, local cuisine at our quaint cafes and restaurants, or take a scenic cruise along the Chester River.
Whether you're seeking a weekend getaway or a leisurely vacation, Chestertown offers a charming retreat for every traveler.
Downtown Chestertown
Dive into downtown Chestertown's charm, boasting over 200 specialty shops, art galleries, restaurants, bars, and more. Discover the vibrant heart of our town!
To download this map as a PDF, click here.
Explore Downtown Chestertown with our new Interactive Map!
Downtown Chestertown now has a beautifully designed interactive map! Whether you're searching for parking, dining, shopping, or accommodations, it's all just a click away—making it easier than ever to discover everything our historic town has to offer.
Visitors Center
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.
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Your Guide to Chestertown
Latest News
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.