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 place where college students are a big part of the character and culture of the town. Small towns have often struggled with declining populations over the past few decades, but the presence of such a large college student population has helped Chestertown to fight this trend. Not only does the college population add spending and jobs to local economy, but it also contributes a very tangible, youthful energy to the town.

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 education level of Chestertown ranks among the highest in the nation. Of the 25-and-older adult population in Chestertown, 43.15% have at least a bachelor's degree. The typical US community has just 21.84% of its adults holding a bachelor's degree or graduate 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.