Poughkeepsie’s Historic Waterfront: Landscapes of Transportation

By Miller Dauk, Geography & Science, Technology, and Society, Class of 2024.

Poughkeepsie traces its origins to its waterfront, where the city had its humble beginnings. Acquiring the nickname “the Queen City of the Hudson” was a testament to its economic and social ties with the river. The city’s ascent began in the 19th century, a period marked by industrialization and driven by the various modes of transportation facilitating the movement of goods and people. During that era, ferries, railroads, railroad bridges, dayliners, and trolleys played pivotal roles as connectors and facilitators of industry and commerce. This second entry in Poughkeepsie’s Historic Waterfront series delves into the transportation technologies and systems that marked the city and its waterfront. 

The transportation ecology of the Hudson River, integral to Poughkeepsie’s history, is incomplete without acknowledging the once-prevalent wind-powered Sloops and Schooners that graced its waters. Serving as the original “superhighway” of the region, the Hudson River was adorned with sailboats, in contrast to current highways teeming with automobiles. The Dutch settlers, leaving their mark, introduced Dutch Sloops –– sailboats with one mast, a mainsail, a jib, and usually a topsail –– that became a prominent mode of transportation. Smaller sloops handled light articles and parcels, while larger ones transported bulk cargo like bluestone, cement, lumber, coal, grain, ice, and brick. These sailboats faced competition from steamboats and mechanical engine boats which gained prominence in the late 19th and 20th centuries. Although sailboats persisted for some decades due to their speed under favorable conditions. Eventually, the consistency of steam and mechanical power was deemed the more favorable option.

Poughkeepsie’s ferry travel evolved through various power sources –– slaves, cables, horses, sails, steam, and diesel. In 1777, Anthony Yelverton initiated the first ferry, operated by slaves rowing between Poughkeepsie and Highland, ending in 1786. From 1793 to 1798, Noah Elting introduced a cable ferry, unique with two masts, sails, and peculiar practices like having horses swim behind for space efficiency. The transition to horsepower occurred in the early 19th century, leading to the establishment of the Poughkeepsie and New Paltz Ferry Company in 1819. Ferries were powered by horses on treadmills. Steampowered boats were introduced to Poughkeepsie when Henry D. Elting, son of Noah Elting, introduced the Dutchess and Ulster to the fleet in 1834. She ran from 1834-1856. In 1875, the ferry company was sold and its name was changed to the Poughkeepsie and Highland Ferry Company.

Painting of the Brinkerhoff coming into the Poughkeepsie docks, by Henry Meuser of Highland (AboutTown blog post)

The disbandment of the ferry boats that once serviced the Poughkeepsie area continued until 1941, the pivotal year. In the painting above, which depicts the Brinkerhoff ferry, the backdrop displays a distinctive bridge, the Poughkeepsie-Highland Railroad Bridge—a good segue to revisit the inception of the Poughkeepsie Railroad and the construction of the bridge.

The railroad first arrived in Poughkeepsie in 1850, known then as the Hudson River Railroad. Discussions about the railroad had surfaced as early as 1832, with investors led by Matthew Vassar contemplating an East-West route. However, concerns from riverfront businesses and industries arose, fearing potential disruption to commerce if the rail line cut through the area. The initial plan for an East-West route did not materialize, and another proposal suggesting a more inland North-South line faced similar challenges. 

These concerns extended to worries about rocky terrain along the water, leading to surveys outside the city of Poughkeepsie that considered a northern route into the countryside rather than along the waterfront. Ultimately, the finalized plans opted to keep the trains running closer to the river. This decision shaped the trajectory of the railroad in the region and influenced the growth and connectivity of Poughkeepsie in the years to come. In 1842, the Poughkeepsie town council created the Hudson River Railroad Central Finance and Correspondence Committee. It was no surprise that the committee was staffed by industrialists such as Isaac Platt and Matthew Vassar. This committee set about organizing local support for the construction and financing of the N-S rail line. 

A view of the original New York Railroad Station in Poughkeepsie, facing northward (Poughkeepsie Architecture: The Poughkeepsie Station. PK Public Library)

The original Poughkeepsie train station, depicted above, was a modest structure, comprising a one-story station situated on the west side of the tracks. Adjacent to this small station, the property also housed a roundhouse and a turntable, operational from 1873 to 1952. These facilities played a vital role for the trains of that era, providing essential daily maintenance and a safe mechanism for turning around to adhere to their scheduled routes.

The necessity for an expanded station had been contemplated since 1859, a mere nine years after its inception. However, it was in 1915 that the urgency for a new and larger station became a priority for the New York Central Railroad. The resulting station, opened in 1918, underwent design and construction by the same engineering firm responsible for the iconic Grand Central Terminal. Intriguingly, the contemporary parking garages that greet modern-day visitors now occupy the space where the old roundhouse and turntable once stood—a reflection on shifting priorities over time.

It’s worth noting that rail travel’s increasing prominence necessitated these expansions. The North-South railroad, still in use today, was not the sole mode of transportation for goods and people. The Poughkeepsie-Highland Railroad Bridge, established in 1889, provided an East-West route across the Hudson River, further diversifying the transportation options available to the region. The historical evolution of Poughkeepsie’s transportation infrastructure paints a vivid picture of the city’s growth and adaptability over the years

The railroad bridge, now known as the Walkway over the Hudson, originally opened in 1889 as the Poughkeepsie-Highland Railroad Bridge. Designed to transport western raw materials to eastern industrial centers, it earned the distinction of being the longest bridge in the world at the time of its construction. Initially, freight trains were the primary users of the bridge, but it soon accommodated passenger trains connecting northern cities such as Boston, Harrisburg, Philadelphia, Baltimore, and Washington DC by 1890.

The Poughkeepsie-Highland RR bridge served various purposes, welcoming an array of specialized train cars. Notable among them were trolley cars modified for both train and trolley tracks, operating between New Paltz and Poughkeepsie. The bridge saw the passage of Special West Point Football trains, circus trains, milk trains, and even trains transporting pigs and cattle. At its peak, the bridge handled an impressive 3,500 cars per day.

Tragically, a spark from a train’s brakes ignited a fire in 1974, leading to its eventual closure. The circumstances surrounding the bridge’s demise included a breeze that fueled the flames, the absence of guards or maintenance personnel, and a ruptured water line meant for firefighting that had not been properly maintained in the previous year. The loss severed Poughkeepsie’s rail connection to the west of the Hudson River. Yet, the railroad bridge remained structurally sound. Renovated as the Walkway Over the Hudson, the structure now stands as the longest pedestrian bridge in the world. While the walkway offers views of modern transportation technologies along the river, it serves as a reminder of the bygone era when historic dayliners used to dock in Poughkeepsie.

Around a decade after the introduction of the railroad, the Hudson River Day Line steamships became a common sight at Poughkeepsie’s Main Street Dock. Beginning in 1863, the Hudson River Day Line succeeded the Albany to New York City Steamboat lines. The company’s fleet initially included the Daniel Drew (built in 1860) and Armenia (built in 1847), with the addition of the new steamer, Chauncey Vibbard (built in 1864. The Hudson River Dayliners transported millions of passengers between NYC and Albany, making popular stops in Catskill, Kingston, Newburgh, Yonkers, and, of course, Poughkeepsie. The image below captures a moment on the deck of a Dayliner as it travels north from New York City, approaching the iconic Poughkeepsie-Highland Railroad bridge.

Passengers aboard a Hudson Valley Dayliner from New York City watch as a train crosses the Poughkeepsie-Highland Railroad Bridge, 1915 (Industrial History: Walkway/Poughkeepsie 1888 RR Bridge over the Hudson River. Blogpost).

The dayliners epitomized an elegant mode of travel through the scenic Hudson River Valley. Renowned for their features, these ships boasted mahogany and turned oak interiors and spacious decks. Passengers on the dayliners were treated to onboard experiences that included entertainment provided by a band or orchestra. The amenities also included writing rooms, newsstands, barbershops, and even a darkroom for passengers to develop photos taken during their journey. As the fleet expanded, additional ships like the Albany, New York, Hendrik Hudson, Robert Fulton, Washington Irving, Dewitt Clinton, Chauncey M. Depew, Alexander Hamilton, and Peter Stuyvesant joined the roster. Despite the emergence of faster travel options such as trains and automobiles, the Dayliner industry strategically positioned itself as a provider of luxury travel experiences. The Hudson River Day Line company sold its business in the late 1940s after the uptick of business during World War II. There were a few steamers still running on a dayliner schedule after this sale. The last survivor of the Day Line, Alexander Hamilton, until 1971 was the last steamboat to function on the Hudson River. 

A view of Poughkeepsie’s waterfront in 1907, showing the railroad bridge being reinforced in the background; the ferry steamer, the Brinkerhoff, is to the left of the dock, and the Marlborough steamer is on the right (Library of Congress).

To conclude this exploration of transportation technologies that once defined the Poughkeepsie waterfront before the dominance of automobiles, the trolley stands out as a significant component in the city’s transportation ecology. In their prime, people could effortlessly navigate the city by riding the trolley, connecting seamlessly from the city center to the ship docks and vice versa. The transition from ship to dock to trolley exemplified the convenience and utility of this mode of transportation. The trolley systems were established in 1894, and the construction process was remarkably swift, with crews laying tracks at an impressive pace of half a mile per day.

The introduction of the trolley system elicited mixed feelings within the Poughkeepsie community. While some were enthused about the prospect of a faster mode of “public” transportation (the trolley was privately operated but acted as a public service), others harbored reservations. Concerns ranged from aesthetic objections to safety apprehensions. Addressing safety concerns, particularly in a time when trolley accidents were reported elsewhere, the Poughkeepsie Eagle published an article praising the city’s motormen. The publication aimed to assure the public about the competence and responsibility of the trolley operators. The quote below from the article emphasizes the dedication of the motormen, seeking to assuage any fears:

“Our electric cars have been running several months, and so far the first accident involving loss of life has yet to be reported. In Brooklyn they are killing so many that the decrease in the population is said to be noticeable. We think our motormen are entitled to hearty praise for their care. One of them told us the other day that so far he had not even struck a kitten, but took occasion to stop to let dogs and cats get out of the way.” March 4,1895

By the 1920s, reports of trolley accidents in Poughkeepsie became more prevalent, yet the prevailing sentiment persisted that the city’s motormen remained reliable and safe. However, a new player emerged on the streets of Poughkeepsie—the automobile, which increasingly became the source of accidents during this period. Despite the challenges posed by the rise of automobiles and ongoing paving projects in the city, the trolley system continued to operate for several years beyond the 1920s. Its last ride occurred on November 25th, 1935. Until its closure, the trolley system remained a dependable means of transportation to the waterfront and the river transport stations.

A film from the Dutchess County Historical Society provides a valuable glimpse into this bygone era. Filmed in the 1930s by Edmund Rawson of Luckey, Platt & Co., the video captures the coexistence and interactions of various transportation technologies on Main Street Dock in Poughkeepsie. This footage serves as an example of how different modes of transportation not only shaped the waterfront but also served as vital nodes of connection, embodying the intricate transportation history in Poughkeepsie 

Today, the post-industrial landscape of Poughkeepsie’s waterfront has a rich transportation history. However, the contemporary waterfront bears witness to a subsequent transformation, with automobiles and car-centric infrastructure almost disconnecting the landscape from its industrial and commercial roots. The third essay, which will focus on the contemporary waterfront, will address Poughkeepsie’s rise and its impacts. It will examine the impact of urban renewal, car-centric infrastructure, the interplay between public and private spaces, and ongoing revitalization plans.

Getting there: 

Main Street dock was at the end of current Main Street, located in present-day Victor C. Waryas Park. As for public transportation, the Poughkeepsie Train Station services MetroNorth and Amtrak. Additionally, the Dutchess County bus service lines stop at the Poughkeepsie Transit Hub (outside the train station). There is a short walk to the park, around the train station, and down Main Street. For drivers, from either the East-West Arterial or the Mid-Hudson Bridge one can navigate to Route 9. Upon exiting Route 9,  drivers can be directed to Waryas Park through a series of smaller streets. 

To Learn More:

Sloops and Schooners:

HRMM Staff. “The Hudson River Sloop.” Hudson River Maritime Museum, Nov. 6, 2016.

Lange, Allynne . “Hudson River Cargoes and Carriers.” Hudson River Maritime Museum, Feb. 17, 2023.

William Edward Verplanck, and Moses Wakeman Collyer. The Sloops of the Hudson, 1908.


Glendon Lloyd Moffett. To Poughkeepsie and Back. Purple Mountain Press, 1994.

Johnson , Carol . “What the Newspapers Said 100 Years Ago – Hudson Valley One.” Hudson Valley One, July 22, 2021.

“Steamer Landings, Poughkeepsie, N.Y.” Library of Congress, Washington, D.C., circa 1908.

Wadlin, Vivian Yess . “A Ferry Tale.” About Town, Summer 2019.


Poughkeepsie Public Library. “Poughkeepsie Architecture: The Poughkeepsie Station.” Poughkeepsie Public Library District, 7 Jan. 2022.

Upper Landing History, “Chapter 6: Rail and Steam at Upper Landing.” Upper Landing Park.

Railroad Bridge: 

Debruler, Dennis. “Industrial History: Walkway/Poughkeepsie 1888 RR Bridge over the Hudson River.” Industrial History, 29 June 2018.

Goldsmith, Gail. “The Industrial History of the Poughkeepsie Railroad Bridge and the Central New England Railway’s Maybrook Line,” Hudson River Valley Institute, 2012.

Shannon Butler. “The Mid-Hudson Bridge – 90 Years of Crossing the Hudson.” Poughkeepsie Public Library District.


HRMM Staff. “The Hudson River Day Line – 1863-1971.” Hudson River Maritime Museum, July 30, 2016.

Lange, Allynne . “Introduction · Hudson River Day Line · Hudson River Valley Heritage Exhibits.” Hudson River Valley Heritage Exhibits, accessed Dec. 1, 2023.

Shannon Butler. “Steaming North – the Hudson River Day Line.” Poughkeepsie Public Library District.


Dutchess County Historical Society. Poughkeepsie’s Boats and Trolleys in the 1930s (Video).

Poughkeepsie Public Library District. “Trolley Time!” Poughkeepsie Public Library District, 2 July 2021.

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