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.

Downtown Master Plan

Main Street is embarking on a Downtown Master Plan with our local partners and a consulting firm to plan the future of Chestertown’s Historic District. Working in concert with the Town’s Comprehensive Plan and the Town’s Strategic Agenda, the Downtown Master Plan will focus on multiple aspects, including infrastructure, streetscape, utilities, tourism, and much more!

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.

Downtown Master Plan

Main Street is embarking on a Downtown Master Plan with our local partners and a consulting firm to plan the future of Chestertown’s Historic District. Working in concert with the Town’s Comprehensive Plan and the Town’s Strategic Agenda, the Downtown Master Plan will focus on multiple aspects, including infrastructure, streetscape, utilities, tourism, and much more!

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.

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GOAL #4

Enrich the streetscapes and waterfront of the downtown area, cultivating a welcoming environment for both residents and professionals alike.

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.

Cross Street in Chestertown, Maryland

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.

Cross Street in Chestertown, Maryland

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.

Cross Street in Chestertown, Maryland

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!

EMAIL

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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