Chesterton was originally called Calumet, and under the latter name was platted in 1852 when the railroad was extended to that point. Chesterton was incorporated as a town in 1899.
The Chesterton Commercial Historic District and the George Brown Mansion are listed on the National Register of Historic Places.
Chesterton High School, or CHS, serves the tri-town area. Chesterton High School operates Chesterton's only local radio station, WDSO 88.3.
Two private schools also operate in Chesterton: St. Patrick Catholic Elementary School and Fairhaven Baptist Academy.
In Chesterton, there are 5 public elementary schools. These are Liberty Elementary School, Bailey Elementary School, Yost Elementary School, Jackson Elementary School, and Brummitt Elementary School. These schools serve grades K-4. After 4th grade, students from Jackson and Liberty will move to Liberty Intermediate School for 5th and 6th grade. Students from Bailey, Yost, and Brummitt will move to Westchester Intermediate School for 5th and 6th grades. After the 6th grade, all students from Liberty and Westchester will go to Chesterton Middle School for 7th and 8th grades. After 8th, students will move to Chesterton High School for their Freshman, Sophomore, Junior, and Senior years.
The town has a lending library, the Westchester Public Library.Media
Chesterton has a local newspaper, the Chesterton Tribune, which is published weekdays and delivered in the afternoons. The newspaper has served the Chesterton area since 1884 and has been published daily since 1961. As well as WDSO-FM, providing local news every hour, on the half-hour
The South Shore Line, operated by the Northwest Indiana Commuter Transportation District, is headquartered in Chesterton. The South Shore Line stops north of Chesterton at the Dune Park station with multiple trains per day to Chicago and South Bend. V-Line's Orange Line route stops near the South Shore station, indirectly connecting Chesterton to Valparaiso University on weekends.
Chesterton's park system includes several large public parks downtown and sports fields. The town is also served by the Porter County Park District and the nearby Indiana Dunes State Park. Several trails connect Chesterton with Porter and the Indiana Dunes National Lakeshore (which is connected to the Indiana Dunes State Park).
Coffee Creek flows through an area that includes downtown Chesterton. The Coffee Creek Watershed Preserve includes a restored section of the creek and its associated wetland.