Chestertown is a somewhat small coastal town (i.e. on the ocean, a bay, or inlet) located in the state of Maryland. With a population of 5,563 people and two associated neighborhoods, Chestertown is the 117th largest community in Maryland.

And if you like science, one thing you'll find is that Chestertown has lots of scientists living in town - whether they be life scientists, physical scientists (like astronomers), or social scientists (like geographers!). So, if you're scientific-minded, you might like it here too.

Telecommuters are a relatively large percentage of the workforce: 9.40% of people work from home. While this number may seem small overall, as a fraction of the total workforce it is high relative to the nation. These workers are often telecommuters who work in knowledge-based, white-collar professions. For example, Silicon Valley has large numbers of people who telecommute. Other at-home workers may be self-employed people who operate small businesses out of their homes.

Chestertown is a small town where college students really create the town feel and character. So many small towns have lost population over the last 20-30 years that having the local college presence in the Chestertown area, with all of the energy of the students filling area dorms and apartments each fall, really helps Chestertown maintain a good economy.

One of the nice things about Chestertown is that it is nautical, which means that parts of it are somewhat historic and touch the ocean or tidal bodies of water, such as inlets and bays. Because of this, visitors and locals will often go to these areas to take in the scenery or to enjoy waterfront activities.

The citizens of Chestertown are among the most well-educated in the nation: 43.15% of adults in Chestertown have a bachelor's degree or even advanced degree, whereas the average US city has 21.84% holding at least a bachelor's degree.

The per capita income in Chestertown in 2022 was $30,459, which is low income relative to Maryland, and middle income relative to the rest of the US. This equates to an annual income of $121,836 for a family of four. However, Chestertown contains both very wealthy and poor people as well.

Chestertown is a very ethnically-diverse town. The people who call Chestertown home describe themselves as belonging to a variety of racial and ethnic groups. The greatest number of Chestertown residents report their race to be White, followed by Black or African-American. Important ancestries of people in Chestertown include English, German, Irish, Italian, and Polish.

The most common language spoken in Chestertown is English. Other important languages spoken here include Polish and Spanish.