EXPLORE
CHESTERTOWN
STREETSCAPE IMPROVEMENTS BEGIN
Chestertown’s exciting new streetscape improvement plan, set to transform the town’s aesthetic and enhance the overall experience for residents and visitors alike has begun! Don’t miss this exciting update on Chestertown’s evolution. Click the link to read the full blog post and envision the vibrant streetscape of tomorrow!
THE CHESTERTOWN CHAT
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.
CHESTERTOWN CAR SHOW
This October, get excited for the Chestertown Car Show! The show accepts all years, makes & models of cars, trucks in 10 classes. There will be over 10 trophies for specific classes, awarded on a judged basis. Food Trucks will be onsite. Beer and Wine will be sold by Mainstreet Chestertown. Registration opens soon!
STREETSCAPE IMPROVEMENTS BEGIN
Chestertown’s exciting new streetscape improvement plan, set to transform the town’s aesthetic and enhance the overall experience for residents and visitors alike has begun! Don’t miss this exciting update on Chestertown’s evolution. Click the link to read the full blog post and envision the vibrant streetscape of tomorrow!
CARNIVAL ON HIGH
Chestertown’s newest Signature Event, Carnival on High, is a highly anticipated summer celebration that ignites the town during July. Transforming High Street into a lively carnival, the event offers game booths and delectable food vendors!
CHESTERTOWN CAR SHOW
This October, get excited for the Chestertown Car Show! The show accepts all years, makes & models of cars, trucks in 10 classes. There will be over 10 trophies for specific classes, awarded on a judged basis. Food Trucks will be onsite. Beer and Wine will be sold by Mainstreet Chestertown. Registration opens soon!
UPCOMING EVENTS
Chestertown is known for some long standing popular events that draw visitors from around the world! Enjoy Chestertown's year-round festivities from the weekly Farmers' Market to our Dickens of a Christmas in December! Join us for our next event, we promise good entertainment, good refreshments and great people!
UPCOMING SIGNATURE EVENTS
EASTERN SHORE
LIFE AT ITS BEST
Main Street Historic Chestertown Inc. is a 501(c)3 non-profit organization which is dedicated to preserving, enhancing, and promoting historic downtown Chestertown, Maryland. Chestertown is located on Maryland’s Eastern Shore on the banks of the Chester River. Established in 1706, this small colonial town encompasses the arts, environment, and history. Come experience Eastern Shore life at its best!
GOAL #1
Main Street Chestertown will play a pivotal role in driving the expansion and diversification of thriving businesses within the downtown area.
GOAL #2
Main Street Chestertown aims to actively promote the growth of the downtown community by fostering an uptick in the residential population.
GOAL #3
To promote and support a diverse range of educational, cultural, entertainment and recreational activities that attract both residents and visitors to downtown.
GOAL #4
Enrich the streetscapes and waterfront of the downtown area, cultivating a welcoming environment for both residents and professionals alike.
2023 CORPORATE SPONSORS
VISIT
Chestertown, Maryland is a charming historical town that offers a delightful blend of history, natural beauty, and small-town charm. Visitors can explore the town’s well-preserved colonial architecture, stroll along the picturesque waterfront, and immerse themselves in its rich maritime heritage. With its vibrant arts scene, local boutiques, and a welcoming community, Chestertown provides a unique and authentic experience that is sure to captivate anyone seeking a tranquil and culturally enriching getaway.
RESOURCES
Find all the answers you need in our comprehensive FAQ section. Discover the best resources to explore Chestertown, ensuring a hassle-free experience during your visit.
LOOKING AHEAD
Looking towards the future of Chestertown, Main Street Chestertown is thrilled to spearhead efforts to nurture and expand the town, fostering its development and prosperity.
VISIT
Chestertown, Maryland is a charming historical town that offers a delightful blend of history, natural beauty, and small-town charm. Visitors can explore the town’s well-preserved colonial architecture, stroll along the picturesque waterfront, and immerse themselves in its rich maritime heritage. With its vibrant arts scene, local boutiques, and a welcoming community, Chestertown provides a unique and authentic experience that is sure to captivate anyone seeking a tranquil and culturally enriching getaway.
RESOURCES
Find all the answers you need in our comprehensive FAQ section. Discover the best resources to explore Chestertown, ensuring a hassle-free experience during your visit.
LOOKING AHEAD
Looking towards the future of Chestertown, Main Street Chestertown is thrilled to spearhead efforts to nurture and expand the town, fostering its development and prosperity.
BY THE NUMBERS
Facade Improvement Grants
Historical Landmarks
Downtown Businesses
Events Hosted Since 2018
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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
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