The town's central business district contains several 19th century commercial buildings, many of which were built during the railroad boom of 1888–1914.

By the time the Great Depression was ongoing, business in Orangeville had started to decline, with the last bank closing in 1932.

Before 1837, the area was occupied by Native Americans who utilized it for hunting grounds; the Sioux tribe had a camp near Oneco.

Curtis died in 1843 and both mills stood idle until John Bower arrived in 1846, with his family, after having visited the area the year before.

A Dr. Thomas Van Valsah led a wagon train from Pennsylvania to Stephenson County in 1837.

[5] At the outset, Bower brought "wagon loads" of lumber from Galena and Chicago to the settlement, and by 1849 he had reconstructed and improved the gristmill.

George Hamilton built a store and soon farmers began to build houses, by 1850 a stagecoach served the area.

That year, the federal government decided that population growth in the two villages warranted the establishment of a post office.

On an appointed day, residents of both villages lined up on the sides of the street according to which town they supported as the location for the post office.

[3] After its incorporation the village continued to prosper, the downtown district was mostly complete by the 1870s, with all commercial lots purchased and improved.

Mel Trotter who established a chain of rescue missions during his lifetime, was born in the village on May 16, 1870, and lived there until he was five years old when his family moved to Polo, Illinois.

The only incorporated village along that line was Orangeville, the railroad came in 1888 and led to commercial building boom.

Between 1888 and 1914, numerous business developed along the corridor of Main and High Streets, those included: restaurants, drug stores, barber shops, banks, watch and clock repair shops, cigar factory, funeral parlor and casket factory, among several others.

By 1928, the decline in the business community of Orangeville was evident; the bypass, coupled with the depression continued to negatively affect the village.

[9] The village of Orangeville is located in northern Stephenson County, about two miles (3 km) south of the Illinois-Wisconsin border directly off of Illinois Route 26.

High Street slopes uphill from the Richland Creek and is populated by historic, 19th century buildings.

[7] At the summit of High Street's slope is the Central House, which is listed on the U.S. National Register of Historic Places.

All other buildings were erected around Central House, which was specifically located and designed to be the center piece of downtown Orangeville.

[5] The People's State Bank was the last major commercial building constructed in historic downtown Orangeville.

In 1980 Community Bank moved to the current church street location on the south end of town.

Though the building was originally constructed to serve as the meeting hall for the local AF and AM Lodge, from its opening it has always been used by all of Orangeville's fraternal organizations.

[3] The Orangeville AF and AM Lodge 687 was chartered October 1, 1872, and its sister organization, Eastern Star, Willow Chapter #434 was founded in 1899.

The Orangeville Independent Order of Odd Fellows, (IOOF) J.R. Scruggs Lodge 372 was formed on October 18, 1868.