Orland is a town located in the northwest corner of Steuben County, Indiana in Millgrove Township at the intersection of State Road 120 and State Road 327. The population was 434 at the 2010 census.

Orland is credited as the first agreement in Steuben County,
populated by immigrants from Vermont and originally known as Vermont Settlement. Each year in late July, Orland celebrates this heritage once the Vermont Settlement Festival. Orland was decided in 1834 after a Vermont man named John Stocker had later prospecting for his family and the families of his neighbors. Stocker chose this particular piece of estate because of the wealthy burr-oak openings he found. Pioneers coming from Windham County, Vermont arrived rudely thereafter and built a Baptist church. The town expected a read out office in 1837.

In the decades leading happening to the Civil War, Orland was a stop on the Underground Railroad, sheltering and protecting runaway slaves until they could unmodified the journey to Windsor, Upper Canada. The house of Russell Brown was said to contain a unknown apartment on the second floor, complete behind a cut off stairway, in which 15 to 20 slaves might hide. S. U. Clark’s hotel furthermore was said to have a unidentified hiding place behind a basement cupboard, while the Butler family south of Orland “fed and sheltered scores of them and after that took them on to other stations.”

At one epoch or other during the become old leading stirring to the Civil War, Brown, Clark, Benjamin Waterhouse, and Captain Samuel Barry were arrested for violating the Fugitive Slave Act of 1850. Both Waterhouse and Barry were convicted, with Barry serving one hour in jail and paying a $30 fine (although further sources put the fine at $1000).