A Modern Town and Moving Forward
A Modern Town and Moving Forward
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Much has changed since 2010, and soon it may be time to begin a new chapter of Olive's history. With Olive Day continuing to act as a community staple and the massive boom in media produced to celebrate the town, it would be easy to assume that, like the previous era, the past fifteen years were relatively stable. However, massive changes similar in scale to those of the "New Era" period would make this far from the reality.
Facebook image posted by the official Olive Day page in 2025 detailing a brief history of the event, although incorrectly assigning the first Olive Day as occurring in 1972.
Same Yet Different
Same Yet Different
In 2016, one such change would happen for the organization of Olive Day: it became funded through non-partisan means.
For over forty years, the annual festival had been sponsored by the town's Democratic party, even as it drew an increasingly bi-partisan attendance, but push back had existed since as early as 2009. Some residents questioned whether or not the party had been paying for the park to be cleaned after the massive event, and others felt that such a staple event should not be one party's event. The opportunity for the town to take over for the event came when the Catskill Mountain Scenic Byway offered a grant to expand the number of events held along Route 28.
However, despite the change in organizer, little has changed for Olive Day beyond continuing to grow. The Frog Jumping competition has continued to be a extremely popular staple, more and more vendors began to sell their wares, and the car show drew unique vehicles from across the county. Even the cancellation of the 2020 Olive Day due to the COVID-19 pandemic did little to alter the town's attitude to the event.
In 2023, another major milestone for both Olive Day and the Town of Olive came around with the 50th annual Olive Day and the 200th anniversary of the town's founding and in order to celebrate, that year's festival was bigger than ever.
Between signs, picture opportunities, bouncy castles, a new museum room exhibit debuted at the Olive Free Library, and the extended hours of the event to facilitate the celebratory firework, the 2023 Olive Day was a showcase of how far the event and the town had come in the fifty years since that very first Olive Day.
While the festival since then have not continued many of the more involved celebrations, Olive Day has continued to grow and showcase many walks of life within the community and many former residents still making the trek back to town to see their friends and relatives.
Wherever Olive Day goes in the future, the impact it has had on the community is undeniable and in many ways it forms the backbone of Olive's annual calendar, especially once the Town Clerk's office began to make calanders in 2018.
The official t-shirt design for the 2023 Olive Day for the Bicentennial of the town. Image from the Olive Day Facebook page.
Some of author's own collection of Olive Day calendars (excluding currently hung up 2025 calendar). Image by author.
A Wealth of Memories
A Wealth of Memories
In 2018, a new souvenir graced the official Olive Day vendor table free for taking: the official Town of Olive calendar for the rest of the year and 2019 and would become a common sight at every year after that.
Within this calendar was a wide array of nostalgia inducing images from both the near and distant past and perhaps surprisingly, no photos of the town before the reservoir. Many months even pulled together images of a single topic from across the years, such as January which showcased a number of local businesses both present and past or June's celebration of past and present graduating classes from the town.
Within this calendar and every one after this, the town would mark important meetings and closures throughout the year and local businesses and organizations advertised themselves both through banners at the bottom of each page and through various entries throughout the year for major events, such as the Samsonville United Methodist Church Holiday Fair on November 9th, 2019.
Compared to the first calendar, the the other calendars are far less varied within their months' themes. with the majority of 2020's months dedicated to one of three things: nature, history, or a single program/event. Additionally, starting with the 2020 calendar, photographs from the previous year and images pulled from the archives from before the reservoir started to become common starting with this calendar, with pictures from the years in between becoming increasingly rare.
Other groups have also started to create Olive-centric calendars as well, with the Olive Free Library occasionally releasing one featuring photographs pulled from their own archives and another calendar published by local author, Nina Shengold, featuring her year long project to take photographs during her walks along the reservior.
A less widely distributed calendar was made for 2021 for the Olive Day which was canceled. Unfortunately, that edition is difficult to obtain and the author has not been able to analyze anything but the cover, which featured frogs social distancing and wearing masks.
Month of July in the 2020 calendar, featuring a variety of images from Olive Rec the previous year. Author even appears on the staff photo in the lower right, first row, third in from the left.
Month of April 2024 in both the Olive Free Library calendar and Nina Shengold's Ashokan Reservoir calendar. Items in author's own collection.
One notable calendard for their content inwas clude the 2024 (created in 2023 for the bicentennial) This calendar heavily focused on the "then and now" theme, celebrating the anniversary, although major events like the Memorial Day parade and Olive Day still received their own months. This lines up with themes present within the Olive Free Library 2024 calendar, showing how the Bicentennial played a major part of Olive residents' conscious that year.
Divisions and Change
Divisions and Change
While this project is not meant to discuss politics, the conflicts within Olive are important for understanding how important the media, programming, and events have been critical for keeping the town together. Several conflicts have been increasingly present in recent years: new-comer vs old-timer, political affiliations, and, most of all, the very vision of what Olive's future looks like.
The first of these is a sentiment that has been around for many years, although it has been exacerbated in recent times thanks to its interactions with other divisions. Where the line between old-timers and new-comers is a bit of a sliding scale depending on the individual's interpretation, but many of the old families consider anyone who moved to the town and sometimes even the children of those individuals as new-comers, regardless of their involvement in the community. But this affiliation runs deep for those who consider themselves old-timers, with some even considering any "new-comer" unfit for public office, especially the individual moved from New York City.
This was not helped by the fact that Olive has had an escalating issue with second home ownership for many years, with many of the homes in town rarely occupied thanks to their owner's primary residence being elsewhere. While many of these second-home owners become part of the town community and some even move to Olive permanently, it isn't uncommon for even new-comers to occasionally mention the "cidiots" who come into town and disregard the town's good in favor of their own needs. This contention exponentially increased during 2020 in the early days of global pandemic as many residents of New York City bought houses for far more than what they were worth in order to escape the crowded city, increasing the price of houses while very few got involved with their new locale.
While not directly related, in recent years, the rift between the political parties has only grown. While some of this is tied to the wider partisanship divide of the United States, in Olive the divide has inserted itself into wide conversations regarding the town in ways it never had before. Some of those along the right political spectrum have been increasingly vocal about their disapproval of the current trajectory of the town, such as the buyouts of buildings within the Boiceville Flood zone, the upcoming Shokan Sewer district and its water treatment plant, and the continued increase of funding directed to the Olive Free Library. Although, some old-timers also bring their own objections to these matters as moving away from the rural heart of the town.
While right-leaning and Republican complaints are easy to assess thanks to their vocality on social media against these issues, it is far more difficult to assess the feelings of Democratic and left-leaning residents to these issues. Although from my own experience, many of these residents feel that these initiatives are key to the community moving forward and continuing to thrive, although many of them are also concerned over the housing prices and the saturation of second-home owners in the community.
Extending Olive Branches
Extending Olive Branches
Regardless of the divisions that have been building, this project is about the ways in which the community has been brought together between the continuing attendance of Olive Day and the release of the various town-devoted calendars, more and more content and efforts have been made intended to honor Olive as a town and to draw the community together.
This oil painting by Kate McGloughlin featured at the 2025 Olive Day in an auction
In the last fifteen years, a wide variety of books, artwork, and other forms of media have been produced about the town. One such book was Melissa McHugh's entry into Arcadia Publishing's Images of America series.
Written by the current director of the Olive Free Library and the archivist who brought the OFL's archive into the modern age, Town of Olive, features a wide variety of images from the OFL's collection and tied into the previously mentioned bicentennial exhibit currently displayed in the library's museum room. Kate McGloughlin, a local artist and a true Olive old-timer, would write the foreword.
A constant community presence, McGloughlin's artwork is frequently the centerpiece of art galleries and auctions. Her pieces depicting the Ashokan pull both from the beauty of the landscape and her family's history as one of the many who were forced out of their homes when the construction of the Ashokan began. She also worked together with the local author, Gail Straub on a number of books combining their talents and mullings on the Olive and the reservoir.
Speaking of the construction of the reservoir, in 2018, Arm-of-the-Sea Theater would debut City That Drinks the Mountain Sky Part 2. Not technically a sequel to part one, the majority of the Part 2 is similar to the original but with updated costumes, props, and dialogue.
Where it truly differs is the extension that brings the narrative into current day, with a focus on how the watershed can only be improved by local residents and New York City working in tandem, rather than a one-sided decisions that had been made by the City in previous years.
Considering the recent updates of the Memorandum of Agreement between NYC and the Watershed communities has given life to many of the demands of the watershed, this message only continues to be relevant.
In 2021, Arm-of-the-Sea Theater filmed City That Drinks the Mountain Sky Part 2 in order for it to be streamed to a variety of schools across New York. In January this year, they made the video available for free on their Youtube page.
Perhaps the most notable effort to connect the town, however, was accomplished in 2025 after years of working towards it.
On September 27th, the grand opening of the Shokan Branch of the Olive Free Library was held at its new home in Olive's American Legion Hall and Senior Center. The culmination of years of fund-raising, grant applications, renovation, and one sadly failed attempt to create a booktruck, the OFL had finally created a space easily accessible to the bulk of the population to check out books and participate in programming.
While much smaller than main branch and open on limited hours, this opening is indicative to the larger efforts of Olive residents to continue building community and place-identity.
Where Now?
Where Now?
This project has been devoted to looking at how Olive has maintained its town-wide identity despite the many divisions that its has faced since the evacuation of the Ashokan basin. But this question raises another; where to next?
Frankly, I'm not sure, but what I do know that is if I and the other residents of Olive continue to love our town and truly want the best for it, we will continue to thrive against whatever will come.
Perhaps one way we can do this is by maintaining our memories of the past through media like we've done since the 1950s and look to the future and our beautiful town since the 1990s. After all, this very project is just another piece of media that will be history in the future. Add onto this my hope that this project will be able to become a host for oral histories that fill in the missing gaps between my knowledge and the physical evidence, and while I do not claim that this project will be the savior of the town, I do hope it will be a resource.
For the readers who live outside of this small town, I ask that you consider your own town's identity and what your community has or has not done to encourage it. Perhaps its time for you to write a history of your own or start an annual festival, or even just connect with your neighborhood. Every place and time is special in its own right and as we continue into the future, we lose the memory of the way it is.
Thank you for reading, everyone.
Ludmilla (Milla) E.
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