Orland is recognized as the first settlement in Steuben County, populated by immigrants from Vermont and originally known as Vermont Settlement. Each year in late July, Orland celebrates this heritage with the Vermont Settlement Festival. Orland was settled in 1834 after a Vermont man named John Stocker had gone prospecting for his family and the families of his neighbors. 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. The town established a post office in 1837.