Each year in late July, Orland celebrates this heritage with the Vermont Settlement Festival.

Stocker chose this particular piece of land because of the rich burr-oak openings he found.

Pioneers coming from Windham County, Vermont, arrived shortly thereafter and built a Baptist church.

[7] In the decades leading up to the Civil War, Orland was a stop on the Underground Railroad, sheltering and protecting runaway slaves until they could complete the journey to Windsor, Upper 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.

"[8] 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.

[10] Fawn River State Fish Hatchery was listed on the National Register of Historic Places in 1997.

[11] During the 2019–20 coronavirus pandemic, confirmed cases of COVID-19 were reported on May 2, 2020, at a local meat processing plant run by Miller Poultry which resulted in sanitation of the plant and the implementation of safety measures such as temperature checks, social distancing & available personal protective equipment for workers.