Because a large number of the original settlers hailed from Vermont, Orland was originally known as Vermont Settlement. Each year in late July, Orland celebrates this heritage with the Vermont Settlement Festival. In the decades leading up to the American Civil War, Orland was a stop on the Underground Railroad, sheltering and protecting runaway slaves until they could complete the journey to Windsor, Ontario, Canada. The home of Russell Brown was said to contain a secret apartment on the second floor, complete with a separate stairway, in which 15 to 20 slaves might hide. .S. U. Clark's hotel also was said to have a secret hiding place behind a basement cupboard, while the Butler family south of Orland "fed and sheltered scores of them and then took them on to other stations." At one time or another during the period leading up 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 1 hour in jail and paying a $30 fine (although other sources put the fine at $1000). Source: http://en.wikipedia.org/wiki/Orland%2C_Indiana