College Hill: History, Development, and Future Potential

By Anna Kaigle, Geography Major, Class of 2025.

Poughkeepsie’s College Hill Park has a history of development and land-use changes spanning the past 200 years. Themes of philanthropy, political power, and public space run through the hill’s story, from its beginnings as a preparatory school to its use as a public park. Placed at the center of this narrative are the wealthy white men who are credited with guiding the early development of College Hill, and often Poughkeepsie as a whole. But before unfolding the evolution of this local landmark, we should remember the contexts of colonization and slavery that allowed Poughkeepsie to grow into the city it is today and which have fueled the hill’s long prominence. 

College Hill resides on Mohican, Munsee Lenape, and Schaghticoke territory, so the history of the hill does not start in the 1830s when the Collegiate school was built at the summit. It began long before European colonizers invaded Uppu Qui-ipis-ing, now known as Poughkeepsie. Many of the industries, parks, and farms that gave rise to Poughkeepsie as a Hudson Valley hotspot found their footing on enslaved labor. Seeing that the gradual process of abolishing slavery didn’t come to fruition in the area until around 1827, we can assume that the forces used to build the school and manicure the lawns of College Hill employed a continuation of enslaved labor, even if often left out of narratives from the time.  

This hill is the highest point in the City of Poughkeepsie, making it a highly sought-after development opportunity in the eyes of city leaders. The hill has also been a contentious topic of debate concerning how best to achieve its full potential, as it has proved influential in shaping Poughkeepsie’s identity throughout history. The hill first appeared on the map in the 1830s, when the Poughkeepsie Improvement Party erected the building that came to be known as the Collegiate School.

A group of prominent white entrepreneurs, local civic leaders who formed the Improvement Party, had aspirations of making Poughkeepsie a bustling village with new industries, churches, streets, schools, and other infrastructures and developments. After purchasing land at the top of the hill in 1835, the Improvement Party aimed to create a prestigious American school to rival schools like the celebrated Rugby School in England. While the school only lasted for about 30 years, it found significant success after its opening in 1836. The school became well established and the student body grew significantly within the first few years after opening. Students came from Europe, Mexico, and from more local areas within the US as well, but it was a school for well-to-do children and families. For example, Franklin Roosevelt’s father attended the school on College Hill. There were visits by US President Martin Van Buren, Senator Henry Clay, and Frederick Douglass gave a speech in August of 1858, in honor of emancipation in the United Kingdom. 

The Collegiate School building (Photograph by Dutchess County Historical Society)

Charles Bartlett was principal of the Collegiate School for many years, which eventually passed down to his nephews, but it was put up for auction in 1865 to settle Bartlett’s estate after he had passed. George Morgan, a wealthy capitalist, then purchased the property. He became very involved in Poughkeepsie and New York social life and politics. Morgan put in a spring-fed lake on the side of the hill, which he had hoped the city would use as a source of drinking water. But ultimately the city resorted to the Hudson River instead, even though Morgan was elected mayor of Poughkeepsie in 1869 and New York State Senator in 1870. Morgan turned the old school building into a summer hotel, attempting to use the scenic Hudson Valley views as an attraction. However, the hotel proved unsuccessful and ultimately failed by 1873, which was possibly due to College Hill’s inability to compete with the nearby Catskill Mountain houses, and the popular vacation destination of Long Branch, New Jersey. 

In 1886, Jon Guy Vassar, nephew of Matthew Vassar, purchased College Hill with plans to repurpose the building as an orphanage, but his humanitarian endeavors came to a halt when he died in 1888. His heirs then disposed of the property, and many competing parties had their eyes on College Hill, with different visions in mind. Some believed the only way for the hill to reach its full potential was through hotel development and private enterprise. Yet, a large number of people pushed for College Hill to become a public park, and their dream came true after the property was put up for auction in 1892. William Wallace Smith (W.W. Smith), of the famous Smith Brothers Cough Drops, announced that he would pay for the park and donate it to the city. He announced this under the condition that alcohol would never be sold at College Hill Park, as this was a time when many people held the values of temperance near and dear. 

Shortly thereafter, W.W. Smith formed the College Hill Park Association to make landscaping improvements and maintain park grounds. In 1893 they widened the road to the summit, added a footpath up the western slope, and connected the reservoir to the summit. In 1894 they hired Aneurin Jones, former superintendent of Central Park and Prospect Park, to prepare a plan for College Hill. In 1896 the association considered their job done and deeded the park over to the city, where Poughkeepsie’s Board of Public Works took over further development of the park. Workers cleared underbrush for picnic areas, planted flower beds, and built a stone wall along Clinton Street. 

This was a time of excitement for College Hill as a public park. W.W. Smith boosted attendance with the summer concerts he hosted on the hill, while many landscaping developments took place. The city hired landscaping designer Downing Vaux, son of the celebrated Calvert Vaux, designer of Central Park, alongside Frederick Law Olmstead. Downing Vaux had ambitious plans for College Hill, including summer houses, spring houses, other shelters, more flower beds and shrubbery, 300 more trees,a fountain, turning the old school building into a museum, and most significantly, adding nearly 20,000 feet of walks and paths to increase pedestrian access. While these plans never fully came to fruition, it shows the importance of College Hill as a landmark, and the prominence of Poughkeepsie at the time.

In February of 1917, the beloved old Collegiate School building burned down when a chimney fire grew out of control, marking a dramatic shift in the appearance and trajectory of College Hill Park. It was a devastating sight, and citizens came to witness the ruins. It took until 1934 for new development to occur on the hill again, as 91-year-old Poughkeepsian Guilford Dudley bequeathed $20,000 to the city for constructing a shelter in honor of the former Greek Revival-style school building. Together with the depression relief money, the $77,000 project built the Parthenon-style pavilion we see at the summit of College Hill today. In 1982, the structure was placed on the National Register of Historic Places along with other historically significant buildings throughout the city. 

William W. Smith Memorial (Photograph by The Poughkeepsie Journal)

There were ideas of adding an elaborate entrance gate to the park, which never found traction, but resulted in the W.W. Smith memorial found at the top of the park today. In 1926, Mayor Frank Lovelace hired a memorial designer to create a $5,000 memorial bench, but once the pile of granite was placed, and stayed there for months, retired sculptor John Ettl took matters into his own hands. He had an affinity for sculpting busts, having sculpted President Lincoln many times throughout his life, and added a bust of W.W. Smith atop a large granite shaft in the middle of the memorial bench.  A large portion of the park as we know it today is occupied by the 30-acre golf course built in 1932. It was designed by local golf enthusiast Horatio Nelson, and funded by the state emergency relief fund to provide jobs to unemployed residents during the depression. 

Throughout the 1930s, College Hill Park “thrived” under the care of superintendent Frank Berry, who was passionate about plants and largely influenced by horticulturist George Saltford, who was the superintendent before Berry.  Berry was also supportive of the park being used for recreational and sporting activities, leading to its prominence as a sledding and skiing hill. In 1971 a combination of state and city funds made for a more formal skiing hill, but upkeep ultimately proved too expensive. Support for recreational activities remained, however, due to an appeal from residents of the nearby Smith Street Housing Project, which suffered from drug dealing, vandalism, and isolation from the rest of the city.

The ensuing “take back” College Hill movement was formed by five city departments, city council members, police officers, and citizens concerned about the presence of marijuana and related groups in the park. The efforts from this movement resulted in the current gated entrance to the park and its one-way road system, part of larger plans for more lighting, tree maintenance, and all-season family activities, which are not seen in earnest today. While well-intentioned in terms of creating a safe space and a park to be used in all seasons, the efforts of the “take back” movement have overall made College Hill less interesting and inviting than it once was. 

Throughout College Hill’s rich history of development, especially its development as a park for the good of the public, there is a common thread of philanthropist figures funding infrastructure and landscaping, fueled by humanitarian, and sometimes capitalist, values. The image of College Hill as a manicured garden, open to the public, with abundant walking paths, shrubbery, and tree coverage, and an impressive Greek Revival-style school building overlooking it all is an idyllic view of the space. This sounds lovely, and at the heart of what a park should be, but it also does not acknowledge who exactly the park was built for, and who was left out of this predominantly white space. We can see clearly in old renderings of the space, that it was made for middle and upper-class white folks to take strolls and picnic the day away on a lush lawn made possible by the efforts of the working class. While College Hill is still a public park and gets used as such, it does not live up to the plans made for it throughout its history. And that is okay, one thing that Holly Whalburg left us with is the notion that each generation must learn what College Hill means to the city. 

Recent happenings on College Hill prove its relevance and an effort to renew its livelihood. A Greenway grant helped to maintain the reservoir and paths around it, the community repainted the basketball courts in 2018, and a collaboration with the Vassar Eco Preserve and Student Conservation Coalition restored the pollinator garden on the hill. One of the most notable recent events was a reenactment of the speech Frederick Douglass gave on College Hill in 1858. In August of 2021, Hamilton Actor Paul Oakley Stovall gave the reenactment, alongside other performances organized by Celebrating the African Spirit, a Poughkeepsie-based group that aims to commemorate the contributions of enslaved Africans and their descendants in building the City of Poughkeepsie. This event attracted a large turnout and exhibited groups from all along the Hudson Valley, showing how College Hill can be used as a meeting spot and community hub for Poughkeepsie. 

Looking into the near future, it is apparent that College Hill has much potential to be a vibrant community hub. The MASS design office in Poughkeepsie has proposed community projects around the city. A handful of projects have been proposed for College Hill, such as using the old baseball field as an amphitheater, making a food truck stop on the flattened top of the underground reservoir, and creating a “champions walk” along the reservoir to honor unsung heroes (a project which has since moved to the Corey Ingram Roundabout). Another proposal aims to create artistic light and sound installations in the emptied underground reservoir, known as the cistern. 

Inside the cistern under College Hill (Photograph by Samuel Stubblefield)

The cistern was built into the side of College Hill in the 1920s, along with new water and sewer mains, under the leadership of Thomas Lawlor, the Superintendent of Public Works. As College Hill has long been an element of Poughkeepsie’s water management, this project aimed to provide drinking water for the city of Poughkeepsie. Although this was a significant project, it was short-lived, like many other projects on College Hill, including the Morgan Lake built in 1872. The cistern went out of use and shifted to an overflow space, but is now almost completely drained, which opens the possibility for the space to be used in another way. As mentioned, one such possibility is for large-scale art, light, and sound exhibits, as the tall cement pillars, rounded ceiling and floor, and echoing acoustics make for an interesting space, even a marvel of sorts.

Comparing College Hill today to the ambitious plans made for it in the past might lead to a rather negative view of its current condition. History has taught us that redevelopment will always be a priority for city leaders and public parks will always be in high demand. When we look beyond urban renewal projects, when we move past simply studying the city from afar, we see a sense of community and hope for the future. College Hill may not be everything W. W. Smith once hoped it would be, but it remains an important historic landmark with reminders of Poughkeepsie’s aspirations for progress. 

Getting there:

Drive or take the L bus from the corner of Collegeview and Fairmont and get off at the closest stop to the corner of Main and N. Clinton St. Drive or Walk along Clinton St for about a half mile until you reach the entrance to College Hill Park. It will be on your right. 

Learning more:

Anthony P. Musso For the Poughkeepsie Journal. “College Hill Park Was Once a College, Hotel.” Poughkeepsie Journal, 22 Sept. 2015.

“College Hill – Dutchess County Historical Society.” Dutchess County Historical Society, 23 May 2023.

Hertz, Larry. “Hidden History – Slavery in the Hudson Valley?” Vassar College, 10 Feb. 2021.

“The Past and Future Potential of College Hill.” YouTube, Walkway over the Hudson, MASS Design, Dutchess County Historical Society, 21 Oct. 2021, accessed 9 Dec. 2023. 

“Revive College Hill Park Coalition.” Revive College Hill Park Coalition, accessed 9 Dec. 2023. 

Spillane, Matt. “‘Hamilton’ Actor Reenacts Frederick Douglass Speech in Poughkeepsie.” Record, Poughkeepsie Journal, 2 Aug. 2021.

“Uphill Battle: Our Epic, Eternal Struggle to Tame Poughkeepsie’s Water.” YouTube, Dutchess County Historical Society, 11 Mar. 2021, Accessed 9 Dec. 2023. 

Wahlberg, Holly. “Statement of Significance: Historic College Hill.” Revive College Hill Park Coalition, 2016.

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