Heritage Shores
Bridgeville, Delaware
Chestertown, Maryland
What It Is Like to Retire in Chestertown
Chestertown is small town of about 5,000 (2020), that is east of Baltimore on the Delmarva Peninsula, and 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., with a large and beautiful 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 Historic District courtesy of Wikipedia and Acroterion, photo of Downrigging at Chestertown courtesy of Wikipedia and CeeBert2004, photo of Washington College Campus courtesy of Wikipedia and Washingtoncollege, Licensed under CC BY-SA 3.0/
Where to Retire in Chestertown and Home Prices
There are active adult communities in the area. The median home value in late 2023 was $345,766, 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.
Crime
The crime rate is similar to the U.S. Average.
Medical facilities
Kent and Queen Anne'sHospital is located in Chestertown as well as the University of Maryland Shore Medical Center. Other hospitals are 25 miles away in Baltimore.
Transportation
Chestertown is convenient to BWI International Airport in Baltimore.
Valuable Links
Historic Chestertown The Chestertown Tea Festival Washington College Academy of Lifelong Learning Maryland retirement guide
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