The site of present-day Valparaiso was included in the purchase of land from the Potawatomi people by the U.S. Government in October 1832.

Chiqua's town or Chipuaw[5] was located a mile east of the current Courthouse along the Sauk Trail.

Located on the ancient Native American trail from Rock Island to Detroit, the town had its first log cabin in 1834.

Valparaiso Male and Female College, one of the earliest higher education institutions admitting both men and women in the country, was founded in Valparaiso in 1859, but closed its doors in 1871 before reopening in 1873 as the Northern Indiana Normal School and Business Institute.

[9][10] There was also substantial activity by the Ku Klux Klan, which negotiated to purchase Valparaiso University in 1923.

[11] The first African-American family to move to Valparaiso faced intimidation and eventually left the city when a visiting relative was murdered.

Today, while the city no longer has a passenger train station, it is still very much a part of the "Crossroads of America" due to its proximity to I-65, I-80, I-90, and I-94.

Additionally, the Canadian National railroad still runs freight on the tracks, including through the downtown area.

The festival also features foot racing events and multiple concerts in addition to typical fair activities.

The Porter County Fair consists of carnival attractions and hosts a variety of shows such as a demolition derby, motocross races, and live musical performances.

[22] There are a number of buildings and districts in the city listed on the National Register of Historic Places.

Bicentennial Park (Burlington Beach Road & Campbell St) – Provides a full range of activities, including a playground, basketball courts, ball diamond and picnic shelters.

Central Park Plaza (Lincolnway and Lafayette St) – is the centerpiece of the Downtown Valparaiso revitalization and opened the summer of 2011.

It has an outdoor amphitheater for concerts and other special events as well as a splash pad in the center of the park for kids to play.

Fairgrounds Park (Calumet & Evans Avenues) – Has the largest complex of ball diamonds and soccer fields in the city.

The park is surrounded by a paved walking circuit that is well occupied on nice days.

Foundation Meadows (Campbell Street & Bullseye Lake Rd) – One of the city's newer parks.

Glenrose South has been the home of the Valparaiso Fourth of July Fireworks display and celebration since 2005.

Kirchhoff Miller Woods, (Roosevelt Road & Institute St – a community park that provides for basketball, baseball, tennis, picnicking and a playground.

Rock Island (Coolwood Dr &, Frontage Rd) is a "tourist attraction" found in front of the Strack & Van Til grocery store just off of the US 30 highway.

The curb that splits the right and left turn lanes has been responsible for a number car crashes and accidents.

This has since been considered an inside joke, featuring its own Google reviews as an official tourist attraction.

[25] Rogers-Lakwood Park (Meridian Road (N Campbell Street)) – Provide opportunities for swimming, fishing, and hiking trails.

Currently, (March 2012) most of the identified bike routes are part of the county's system of recommended roads and streets.

These travel east 2 miles (3.2 km) on Glendale, ending on North Calumet at the Walgreens corner.

[28] Valparaiso University was founded in 1859, and occupies 310 acres (130 ha) on the south side of the city near downtown.

Indiana State Road 2, which connects South Bend and Lowell, passes through the southeast corner of the city.