[2] The largest community in Fayette County, it is located at the junction of State Highways 3 and 150.

[3] The town of Oelwein was laid out in a corn field purchased from pioneer settler Gustav Oelwein on the coming of the Burlington, Cedar Rapids and Minnesota Railroad (later called the Rock Island) in 1872.

Some years later the two dividing streets of Oelwein were named after his sons, Frederick and Charles.

The hamlet of Oelwein was instituted in 1873, and was incorporated as a town in 1888, with Dr. Israel Pattison becoming its first mayor.

The town suffered its chief setback in 1887, when nearly all of the old Main Street business district (now First Avenue SE) was destroyed by fire.

By January 1892, Oelwein was chosen to become the center of the Chicago Great Western Railway; the CGW made the town the site of their locomotive and car repair shop, where four lines converge.

[4] Oelwein was one of few Iowa towns to experience an influx of Italian immigrants who were employed in the railroad industry.

In 1968, the town suffered another setback when a large tornado swept through the main business district.

Transco employees donated their time to refurbish a Chicago Great Western EMD FP7 diesel locomotive that is displayed near the Hub City Heritage Museum, 26 2nd Avenue SW, the museum of railroad memorabilia.

The 2009 book Methland: The Death and Life of an American Small Town by Nick Reding (Bloomsbury Press) documents the drug culture and how it ties into larger issues of rural flight and small town economic decline placed in the historic context of the drug trade.

While Reding's book received positive reviews from the New York Times Sunday Book Review[5] and Washington Post's Book World,[6] it was severely criticised by Cedar Rapids columnist Laura Behrens, who wrote, "it is so ridden with errors of basic reporting that the credibility of its larger premises is crippled", pointing out several factual errors.

Recreational opportunities include public parks, campgrounds, children's playgrounds, and picnic areas.

Tennis courts, a skateboard rink, and softball diamonds are at Wings Park.

Dedicated to Walter P. Chrysler, who once resided in Oelwein, the part to the east offers a gazebo with picnic facilities, water fountain, flower gardens, and a planting of Thunderchild Flowering Crabapple Trees, received through an Arbor Day Challenge Grant and Oelwein Trees Forever.

The second part holds the Korean and Vietnam Veterans Memorials, donated by the Robert McNamara family in 1998.

The park offers picnic shelters with tables, open play area, tennis court, sand volleyball, horseshoe courts, restroom facilities, a dog park, modern and primitive camping, and a dump station.

Located at 4th Avenue and 4½ Street SW, this park offers picnic tables, an open play field, and is bordered by a natural wooded environment.

Located at 7th Street and 7th Avenue SE, this park offers 1.25 miles (2.01 km) of footpaths, picnic shelters and tables, playground equipment, horseshoe court, restrooms, and a large playfield.

This park is the home of a Gazebo and "Trail of Dreams" created by Oelwein Care Center.

Located at 4th Street and 5th Avenue NE, Wings Park is the home of the Oelwein Family Aquatics Center.

By 2019 it sustained a decline in income and in the number of students and established a GoFundMe to stave off closure.

[16] In addition, Oelwein is also home to the Regional Academy for Math and Science (RAMS).

RAMS provides a curriculum for high school and college students and serves as a summer regional center for gifted and talented programs.

RAMS also partners with the regent universities to offer summer coursework for teachers.

It features a variety of fitness and dance classes, circuit weight and cardiovascular equipment, a gymnasium and indoor track.