In order to truly understand why it is notable that Olive as a town maintains a strong, cohesive place-identity (meaning a set of traits, traditions, and identifiers which those who assert themselves as residents share), the background of the town's history both as a physical location and as a social designation is key. This is especially true as these aspects of the more recent aspects of the town's past become the core of what ties the community together.
While not directly tied to why the Olive Identity has persisted, the history of what would become the town prior to the arrival of Europeans remains an important part of the history of the land.
As part of the Catskills, Olive and the Esopus Valley's landscape were formed through eroded plateau caused by the advancement and retreat of glaciers over hundreds of thousands of years during the ice age over 10,000 years ago. This would leave the aforementioned Esopus Valley relatively flat and easy to farm — at least compared to the essentially exposed bedrock of the mountains which would make of the eastern half of the area.
A topic of particular interest even to residents in the 1800s, indigenous peoples likely at least passed through what is now Olive and its nearby mountains well before the first confirmed artifacts found in town, dating to around 5,700 BCE. Even after this era, it is difficult to tell how frequently Olive's chunk of the Esopus Valley and Catskill mountains were utilized by groups like the Lenape, with very little accessible evidence of their presence. Not to say there is no evidence, there have been the 8 rock shelter sites —cave like-structures that were usually seasonal or short-term shelter used when hunting large game— in the area which have been excavated and confirmed by experts on top of rumors dating back to at least the early 20th century of a village site and burial ground located in what is now the Ashokan Reservoir's basin.
Notably, several local words and names are said to have been derived from "Native American" words, like Tongore and Onteora. Many of these words only have speculated meaning let alone confirmed origin, such as Ashokan/Shokan, which has been identified by different sources as originating from a Lenape language and others from Iroquois, which are not even considered to be in the same language family.
Regardless of how prevalent the Lenape, the Iroquois, or any older groups of indigenous peoples were in the area in the years before, by the time of the first European settler, there was no sign of any recent inhabitation.
Even before the first settler arrived in town, the land that comprises Olive was already deeded to a variety of individuals by the English monarchy starting in 1703. The Marbletown Patent along the Esopus Creek comprised the majority of the desirable land, although significant amounts of land would also belong to the Hardenburgh Patent to the south-west. Despite this granting of land to families like the Broadheads and Bogarts (still notable names in the region), it wouldn't be until 1740 that anyone settled in the area.
However, after this first settler, the Esopus Valley would quickly gain a sizeable population, comprised primarily of farmers although mills, quarries, and tanneries would also pop up in the area along with the businesses and stores that helped sustain the local population. By 1823, this population felt that the distance of travel required to get to the administrative centers of the various towns the Valley belonged to was too long and a movement to establish a new town.
This town would take land from Marbletown, Shandaken, and Hurley — and later exchange with land with Woodstock to its north — and would reach a population of over 3,000 by 1860. The town continued to thrive, with boarding houses also becoming popular as the Ulster and Delaware Railroad established a train station in hamlet of Shokan. However, this growth was not to last very long.
As Olive entered into the 20th century, an outside force would drastically affect the town. New York City's supply of clean drinking water had been a constant struggle for more than a century. As early as 1896, officials looked beyond even the Croton Reservoir System and eventually came to the Catskill mountains after much debate and legal struggles, Olive and West Hurley's section of Esopus Valley was chosen as the site of a new reservoir.
This was massively unpopular with the residents of the valley, which comprised the majority of the population of Olive and almost the entirety of hamlet of West Hurley. Although once the reservoir was an inevitability, many would begin legal action against the City for the amounts New York City was to pay for their property taken under eminent domain. Rightfully so, many felt that the amount they were promised was an vast underestimate of their property's value, especially given the generations of families that had run businesses and lived in the valley.
But many of these legal fights fell through and many families lost their main incomes as the land that would become the basin had to be raised to the bare earth, including the relocating of bodies of the residents' ancestors who had been buried in the valley. Some families left permanently, some were unaffected beyond the loss of their community's center, some simply relocated into the outskirts of the town. Some even managed to scrape a few more years on their land by renting their homes from New York City while the preparations for the Ashokan Reservoir's construction began.
In 1913, the final evacuation notice was issued to the few residents still residing in the basin, and with that, this project's story begins.