The Best Places to Live & Explore…
For Every Lifestyle

Living a Boating Lifestyle in Chestertown, Maryland

Chestertown is an old seaport town of about 5,000 people. In the mid-eighteenth century Chestertown was considered Maryland's second leading port after Annapolis. There are still some pleasure boats based here who enjoy local cruising. It is located east of Baltimore on the Delmarva Peninsula, east of Baltimore on the Chester River.  . Chestertown is home to Washington College, the 10th oldest college in the U.S. Chestertown was named  to the 2007 list of America's Dozen Distinctive Destinations by the National Trust for Historic Preservation.

Where to Retire in Chestertown and Home Prices

There are active adult communities in the area (see link at top left). The median home value in late 2020 was $239,161 according to Zillow.

What Is Special about Chestertown

Chestertown is a beautiful old river town with a rich history and many historic homes and buildings. The town was named as one of America's best rural places to live. The Chestertown Tea Festival celebrates Chestertown's colonial heritage with  events including a re-enactment of the legendary Tea Party that was held shortly after the Boston Tea Party.

What Is Not Special about Chestertown

It's expensive to live in Chestertown.

Climate and Physical Environment

Chestertown is on the Chester River on the east side of the Chesapeake from Baltimore and Annapolis.The average July high temperature is 88 and the average January low is 25. September is the wettest  month with over 3" of rain.

Restaurants & Cultural Scene

The Chestertown Tea Festival is a big annual event. Washington College contributes to the cultural life of the town.


The Chestertown crime rate is similar to the U.S. Average.

Medical Facilities

Kent and Queen Hospital is located in Chestertown. Other hospitals are 25 miles away in Baltimore.


Chestertown is convenient to BWI International Airport in Baltimore.

Your Stories about Chestertown, Maryland

Add Your Story

Discuss this review of Chestertown in the Forum

If you have suggestions on how could improve these reviews, contact us.

Suggest a community that you think is a great place for this lifestyle.

Tell us Your Story about this lifestyle or city. Add a Video about it.

Find Your Dream Lifestyle


Rate This Town