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 5,590 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.

Of important note, Chestertown is also a town of artists. Chestertown has more artists, designers and people working in media than 90% of the communities in America. This concentration of artists helps shape Chestertown’s character.

Also of interest is that Chestertown has more people living here who work in computers and math than 95% of the places in the US.

A relatively large number of people in Chestertown telecommute to their jobs. Overall, about 11.14% of the workforce works from home. While this may seem like a small number, as a fraction of the total workforce it ranks among the highest in the country. 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.

Chestertown is also nautical, which means that parts of it are somewhat historic and touch the ocean or tidal bodies of water, such as inlets and bays. Quite often, nautical areas such as these attract visitors and locals who come to enjoy the scenery and various waterfront activities.

As is often the case in a small town, Chestertown doesn't have a public transportation system that people use for their commute.

The education level of Chestertown ranks among the highest in the nation. Of the 25-and-older adult population in Chestertown, 45.12% 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 $32,565, which is low income relative to Maryland, and middle income relative to the rest of the US. This equates to an annual income of $130,260 for a family of four. However, Chestertown contains both very wealthy and poor people as well.

Chestertown is an extremely 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, Italian, German, Irish, and Polish.

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