The first American automobile race takes place over the 54 miles from Chicago's Jackson Park to Evanston, Illinois. Frank Duryea wins in approximately 10 hours.

The Chicago Times-Herald race was the first automobile race held in the United States. Sponsored by the Chicago Times-Herald, the race was held in Chicago in 1895 among six motorized vehicles: four cars and two motorcycles. It was won by Frank Duryea's Motorized Wagon. The race created considerable publicity for the motocycle, which had been introduced in the United States only two years earlier.

Jackson Park is a 551.5-acre (223.2 ha) urban park on the shore of Lake Michigan on the South Side of Chicago. Straddling the Hyde Park, Woodlawn, and South Shore neighborhoods, the park was designed in 1871 by Frederick Law Olmsted and Calvert Vaux and remodeled in 1893 to serve as the site of the World's Columbian Exposition. It is one of the largest and most historically significant parks in the city, and many of the park's features are mementos of the fair—including the Garden of the Phoenix, the Statue of The Republic, and the Museum of Science and Industry.

Evanston is a city in Cook County, Illinois, United States, situated on the North Shore along Lake Michigan. A suburb of Chicago, Evanston is 12 miles (19 km) north of downtown Chicago, bordered by Chicago to the south, Skokie to the west, Wilmette to the north, and Lake Michigan to the east. Evanston had a population of 78,110 as of 2020.

James Frank Duryea was an American engineer and inventor who, with his brother Charles (1861–1938), made the first American gasoline-powered automobile.