The most populous city in the county, Baraboo is the principal city of the Baraboo micropolitan statistical area which comprises a portion of the Madison combined statistical area.

Baraboo is near Devil's Lake State Park and Aldo Leopold's Shack and Farm.

[8] The current community was established by Abe Wood in 1838, and was originally known as the village of Adams.

[12][13] In the 1860s, the city had surpassed a population of 2,000, and many businesses started to form, including grocery stores, banks, and hotels.

In 1884, the Ringling Brothers Circus was established in Baraboo by circus performers and tourers the Ringling brothers, after they settled in the city in 1875 and performed their first show in Mazomanie, Wisconsin in 1882.

[14] It was later demolished and now the land is a part of the Sauk Prairie Recreation Area.

[15] Hank Snow's 1959 song "I've Been Everywhere", famously covered by Johnny Cash, mentions visiting Baraboo.

Cirrus, a manufacturer of single-engine aircraft, was founded in a rural Baraboo barn in 1984 by the Klapmeier brothers.

[16][17] After a few years of designing the VK-30, they relocated to the Baraboo–Dells Airport and in 1994 moved the company to its present-day home in Duluth, Minnesota.

[20] The nearby Baraboo Hills are designated one of the "Last Great Places" by the Nature Conservancy because of its rare rocks, plants and animals.

The hills were created by glacial action, and in some points poke up from the flat terrain to form a stark contrast.

Some of these features were created when a glacial pocket was formed during the Wisconsin glaciation where the advance of the glacier halted, along the edge of what is known as the Driftless Area.

A city hall building opened in 1967,[24] and another location finished construction in 2018 at a cost of $9 million.

The middle school has a swimming pool that can be accessed by the public with a seasonal membership option.

The current school building, designed by the Wisconsin Rapids company Billmeyer and Sons and with a cost of over $500,000, has 11 classrooms.

The second building for the school opened on a filled-in ravine in 1912, northeast of its associated church.

The Baraboo-Wisconsin Dells Airport (KDLL) serves the city and surrounding communities, and is located on Bus.

The Wisconsin & Southern Railroad provides freight rail service to Baraboo via the Reedsburg Subdivision, the nearest Amtrak passenger rail station is in neighboring Wisconsin Dells.