Chestertown : Maryland


What It Is Like to Retire in Chestertown

Chestertown is small town of about 5,000 that is east of Baltimore on the Delmarva Peninsula, northeast of Annapolis on the Chester River.  The population is growing as more people consider it a quiet alternative to places like St. Michaels. In the mid-eighteenth century Chestertown was considered Maryland's second leading port after Annapolis. Chestertown is home to Washington College, the 10th oldest college in the U.S. The College has a large campus as you enter town. Then the charming downtown is set around a square and the Courthouse. Beautiful brick and wood houses are close together along some very cute streets. Chestertown was named  to the 2007 list of America's Dozen Distinctive Destinations by the National Trust for Historic Preservation. Photo of Chestertown from above courtesy of Wikipedia and Jennifer Schmidt in the public domain.


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.

Who Will Like Retirement in Chestertown

People who like small towns with a lot of history and access to the water might like Chestertown. Washington College offers the Academy of Lifelong Learning for adults with many classes from which to choose and volunteer opportunities.


Local Economy Is Driven by

There is some tourism in Chestertown. Many people commute to other places.

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.

Valuable Links

The Chestertown Tea Festival
Maryland retirement guide
Progressive Farmer award for Best Rural Place

Washington College Academy of Lifelong Learning


What people are saying about Chestertown

Chestertown MD
Chestertown has long been on my retirement radar but with recent changes, not so much anymore. One of the few good restaurants in town has closed as well as the movie theatre making it a 30 mile drive to the nearest larger town, Middletown, DE, for a movie and box store shopping. The hospital, which is now run by the University of Maryland Medical Center is constantly rumored to be closing. Wish the was more of a positive upswing to the town but it doesn\'t seem to be happening. It is charming, however, and for boaters and nature lovers opportunities abound.
Posted by Staci on October 12, 2017

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