Before European settlers arrived the valley was home to a tribe of Lenape Native Americans, who gave Oley its name.

In the Lenape's Unami language, "Olink" means kettle, which is roughly the shape of the valley, which was an important meeting place for Native Americans.

The first settler, named John Palmer Fleck of Wyomissing, Pennsylvania, moved to the Maxatawny region of the Oley Valley.

One day it was reported that a nearby farmer had been killed by Indians and the entire town gathered in the largest house.

That night, sentries were posted and all men with their muskets were positioned at small firing ports cut in the building's wall.

The farmer had no knowledge of his supposed death and informed the townspeople that in the middle of the night all the Lenape had disappeared from the Oley Valley.

One of the most prominent people in the history of early Oley was Mountain Mary Originally named Anna Maria Jung, she was a German immigrant who practiced pow-wow, also known as Braucherei, and she had an extensive understanding of herbal remedies for various ailments.

She kept one cow and did her own baking and some light farming, common for the era, but made her income primarily by keeping bees and making butter.

[3] Various exhibits were housed inside the school including the Home Economics, Fruit and Vegetable Departments, as well as some commercial displays.

The fair was also able to purchase 2.5 acres (10,000 m2) of land adjacent to the Oley Fire Company grounds which is used for additional parking.

The Fair has become a community tradition and some people work hard for the entire year to grow a prize-winning fruit or vegetable.

The fair is also famous for its food, which is prepared by volunteers, not commercial vendors, and is cooked in traditional Pennsylvania Dutch style.

In the winter of 2006, construction began on a 130 home 55 and older community built on 30 acres (120,000 m2) of land, next to the elementary and middle school.

Many people have complained that these developments harm the rural and historical heritage of Oley and increase the tax burden, and that local government has failed to enact appropriate zoning to protect and preserve farmland.