The town site of Poughkeepsie - the name derives from an Iroquois word meaning “the reed-covered lodge by the little-water place” referring to a small spring that fed the Hudson River - was settled by the Dutch in 1659, just a few years before the English would seize control of the entire region. Poughkeepsie would emerge as the mid-Hudson Valley’s largest and most influential city on the east bank, growing rapidly and even enjoying a two-year stint as capital of New York after the American Revolution. In addition to the Hudson River the town sat on two other important Colonial transportation routes - the Albany Post Road and the New Hackensack Road. 

Lumber and grain milling were the first important industries and the town became a major center for whale rendering early in the 1800s. There were also glass factories, textile mills, ball bearing manufacturers and breweries. After the Civil War Poughkeepsie experienced a period of rapid industrial expansion, with a corresponding increase in population. By 1854 Poughkeepsie’s population grew to 20,000. But the city’s economic triumphs failed to register on the national radar. Instead, as Poughkeepsie boomed, homes and businesses began constructing individual wells and cisterns for sewage disposal. This activity caused groundwater contamination resulting in epidemics of cholera, typhoid fever, smallpox and diphtheria, which claimed hundreds of victims. To the City’s embarrassment Poughkeepsie was heralded in newspapers as “The Sickly City,” even as far west as Chicago. One account called Poughkeepsie, “A fine place to live, with fine schools and churches and railroad accommodations, well governed but oh, how sickly.” 

In 1870 a general election to decide the question of whether or not to develop a public water supply resulted in a vote of 544 to 43 in support of the proposal. On this basis a Water Board was formed which sought out an engineer for the project. In 1871 progress moved dramatically forward as Harvey G. Eastman was elected Mayor. Mayor Eastman was credited as the driving force that carried out the public wishes. Through his leadership, gift of persuasion and vision the first successful slow sand filtration plant in America was placed into service July 8, 1872. The success of this project was heralded as epidemics all but disappeared and the plant was copied across the land and to this day Poughkeepsie is recognized as the national leader in filtration.

Our walking tour of today’s “Queen City of the Hudson” will begin at the entrance of Harvey Eastman’s park and a memorial he donated to the city, a water-based memorial naturally...  

Soldiers’ Fountain
entrance to Eastman Park
South Avenue/Market Street and Montgomery Street

Unveiled in 1870 to the memory of the soldiers of the Civil War, the ornately figured fountain is an example of folk art in cast iron. I.P Victor Andre designed the 26-foot high monument. It has been said that the square in which it stands preserves more mid-Victorian civic atmosphere than any other civic square in the State. Harvey Eastman contributed the $70,000 for its construction. Eastman began his professional career teaching at the Eastman Commercial College in Rochester, which had been founded by his uncle, George Washington Eastman. In December 1855, he founded a school of his own in Oswego and then headed west to St. Louis. His anti-slavery leanings forced him to return east to Poughkeepsie where his Eastman Business College became one of the largest commercial schools in the United States. The school made him rich, and he became one of the leading citizens of Poughkeepsie, serving as mayor from 1871-1874 and again from 1877 until his death. His tenure as mayor is most notable in his ensuring the construction of a water filtration plant that eliminated Poughkeepsie’s reputation as “The Sickly City.”


Adriance Memorial Library
93 Market Street  

The French Renaissance building of white marble was constructed as the city’s library in 1898. The single-story Tennessee marble domed building features a parapeted roof, projecting cornice with modillions, plain frieze and central pavilion with four Corinthian columns. Decorative panels on the facade feature torch and swag motifs. The Adriance family, manufacturers and financiers, donated $100,000 for its construction as a memorial to their parents. John Adriance had begun his long business career in Poughkeepsie as a silversmith’s apprentice at the age of 14 in 1809. Adriance’s fortune was built on his development of the buckeye plow that helped tame American soils. Books were lent in Poughkeepsie as far back as 1839 and the library led a peripatetic existence around town until the establishment of this permanent home. The cannon on the lawn was carried on the ironclad USS Monitor that battled the CSS Virginia to a draw in the world’s first battle of metal-armored warships during the Civil War. It was built through the efforts of John F. Winslow and John A. Griswold and with money furnished by them. The cannon was donated by Winslow’s daughter, MaryC.W. Blake in 1926.

Market Street Row
west side of Market Street opposite Noxon Street

Market is the city’s oldest street, running parallel to the Hudson River since 1709 when a royal decree made it part of the King’s Highway. Urban renewal and highway building in the 1970s swept away many of the surrounding homes but this little group dodged the wrecking ball. As such, the Mott-Van Kleeck House at the center of the trio is the oldest frame house in Poughkeepsie, built around 1780. The neighboring houses came along a century later, ornate Victorian structures with towers and dynamic massing. A tower was added to the Mott-Van Kleeck House in lock-step with its neighbors. Targeted by preservationists, the three structures have been redeveloped into office space. 

Hasbrouck House
75 Market Street

Frederick Clarke Withers was an successful English architect in America, especially renowned for his Gothic Revival church designs. But for this red brick house built in 1885 for Frank Hasbrouck, a local judge and historian, Withers dipped into his Romanesque Revival playbook. He created the city’s most distinguished building in that popular Victorian-era style accessed via a recessed front porch with dual round-headed arches divided by a spiral column with molded floral design and Corinthian capital. On the upper stories, there are brownstone windowsills and courses around the house. Other ornaments include an oriel window on the second story, pentagonal dormer on the third, and a parapet roofline. The house was shepherded into the 21st century by the United Way.

Not Amrita Club
southeast corner of Church and Market streets

Poughkeepsie’s most prestigious private club organized in 1873, meeting in rented rooms around the city until 1912 when it sunk $100,000 into this Colonial Revival clubhouse. Constructed of brick, the three-story structure is trimmed in marble. The club’s importance waned in the latter decades of the 20th century and disbanded in the 1980s. The building reverted to the city and endured a long spell of vacancy and has yet to regain useful footing. 

New York State Armory
northeast corner of Church and Market streets

New York State is dotted with 19th-century armories designed by Isaac G. Perry of Binghamton, the state architect at the time. This eclectic Romanesque-flavored design from 1891 is one of his best. Crafted with red brick and rusticated sandstone, the building is still in use as an armory, as home to the Company A, 101st Signal Battalion of the New York Army National Guard.

Young Men’s Christian Association
58 Market Street

After meeting for years in more pedestrian digs as the Young Men’s Christian Union, the YMCA moved into this spectacularthree-story Renaissance Revival home in 1908. William Wallace Smith of cough drop brothers fame covered the $200,000 in construction costs. Smith also spent $65,000 for an office building next door, paid to cancel the mortgage on the previous building and wrote a check for $10,000 for pocket change. The New York City firm of Jackson & Rosencrans drew up the highly decorative plans that included a molded cornice, corner quoins and a rooftop balustrade with an elaborate cartouche.  The YMCA has a glazed terra-cotta front facade, the only building in Poughkeepsie using that material. 

Farmer’s and Manufacturer’s Bank
43 Market Street at Cannon Street

The three-bay, two-and-a-half story brick building was opened to the public in 1835, the year after it was built. It stands as one of only two non-residential Greek Revival structures in downtown Poughkeepsie. Signatures of the then-popular style include the wide frieze and pilasters on the first story, eyebrow windows, balustrade and cupola. The brick is complemented by stone trim, particularly around the windows. First-floor ornamentation includes a stone entablature with dentil molding and four laurel wreaths. Save for a front porch that was removed in 1892, the building’s exterior has remained the same for over 175 years. The same could not be said for the bank; after becoming Empire National Bank it relocated.

Bardavon 1869 Opera House
35 Market Street

The Bardavon stands as the oldest continuously operating theater in New York State. The stage was opened as the Collingwood Opera House by its owner and operator James Collingwood in 1869. Prominent Poughkeepsie architect J.A. Wood provided the theater with a unique two-stage dome. It became the Bardavon in 1923 after being outfitted for the golden age of film and continued as a movie palace until 1975. The venerable exhibit house then faced the wrecking ball but its destiny as a parking lot led concerned citizens to save the theater and get it named to the National Register of Historic Places on August 20, 1977 ― and rechristened as The Bardavon 1869 Opera House. 


Poughkeepsie Savings Bank
21-23 Market Street

This was the third home for the bank that was chartered as the city’s first in 1831. The plans were drawn up in 1911 by bank architects Louis Mowbray and Justin Uffinger. They delivered a Classical Revival building, with slightly trapezoidal walls reflecting the constraints of the site. Its front facade, made of Pennsylvania marble on a granite base, uses two Ionic order columns flanked by Doric pilasters. The deeply recessed entryway and vestibule is done in cast bronze and ornamental glass.

Smith Brothers Restaurant
13-15 Market Street

Serendipity named them Trade and Mark, and their images have been commercially reproduced more times than any others. They were so successful they spawned a spate of cheap imitators such as the “Schmitt Brothers” and the “Smythe Sisters.” They are the Smith Brothers. James Smith was a Scot who emigrated to Quebec, Canada for fifteen years before migrating to Poughkeepsie, where he opened a restaurant on this site in 1847. He sold candy as a sideline, with his oldest son William hawking the confections so successfully he was known around town as “Candy Boy.” Legend has it that one day a peddler stopped in the restaurant, and not having the money for a meal, swapped a cough drop recipe for some food. Whatever the origins, by 1852 James Smith & Sons Compound of Wild Cherry Cough Candy was on the market “for the Cure of Coughs, Colds, Hoarseness, Sore Throats, Whooping Cough, and Asthma.” The claims were later toned down, but if there was anyplace that needed such a remedy, it was the bitter, windswept Hudson Valley. James Smith died in 1866 and the Smith brothers, William and Andrew, inherited the business. The next generation concentrated more on the cough drops than the restaurant. They converted a barn on the edge of town into the the first cough drop factory, and sold their Smith Brothers cough medicine in glass countertop jars. To discourage counterfeiters, the brothers molded the initials “SB” on each drop - and began advertising the fact. To further thwart imitators they developed a trademark based on their own bearded visages. To announce the government protection they printed the word “TRADEMARK” on the label where it was divided: the “TRADE” by chance appearing under William’s picture and the “MARK” resting under Andrew. The labels were pasted on the glass jars. In 1877 the Smiths produced one of the first “factory-filled” consumer products by selling their black licorice and cherry cough drops in small packages - each adorned by Trade and Mark. In their lifetime, William and Andrew Smith saw production of their cough drops soar from five pounds a day in the back of the restaurant here to five tons daily. Andrew died in 1895 and William in 1913. The business would remain in family hands until 1963, but the only Smiths anyone ever knew were Trade and Mark. The last Smith Brothers Cough Drop manufactured in Poughkeepsie was made in 1972. 

Dutchess County Courthouse
10 Market Street at Main Street

This site has been occupied by a county courthouse for nearly 300 years; this is the third to stand here and each had about a 100-year run. The original was constructed in 1720 and served until it was destroyed by fire in 1806. During a brief moment of glory that building hosted New York’s debate on ratifying the United States Constitution when Poughkeepsie served as the state capital in 1788. Its replacement wore out in 1903 and was replaced with the current structure that was designed by local architect William J. Beardsley and carried a $500,000 price tag. Beardsley gave the four-story building a Colonial Revival look with Palladian windows in the central bays and stone corner quoins and keystones over the windows. Because of a requirement in the original deed for the land, one of the original 1720 courthouse’s jail cells must remain in the basement of this or any subsequent court building. 

Church Corner
1 Main Street on southeast corner of Market Street

For nearly two hundred years this prominent downtown corner was the site of a cemetery for the original church cemetery, hence its name. The buildings that rose here in the 19th century were architecturally non-descript. The stylish Art Deco facade seen today dates to the 1930s.


Poughkeepsie Trust Company
236 Main Street 

Local architect Percival Lloyd left nary a surface undecorated for this Beaux Arts confection for the Poughkeepsie Trust Company in 1906. The bank had started on this site five years before and was successful enough to sink $100,000 into this ornately carved stone landmark. The ground level is totally quoined and sports an intricate wrought-iron gate on the main door and decorative Doric columns. On the sides, a red-and-yellow brick diamond pattern runs from front to rear at the fifth story. At six stories, it laid claim to being the Hudson Valley’s first skyscraper and boasted one of the city’s first elevators. The county took over after the bank departed and it now houses the district attorney’s office.

Village Hall and Market
228 Main Street

This two-story, late Federal-style brick building was constructed in 1831 at the cost of $20,000 to serve as both village hall and a public market. Four bays wide and seven bays deep, the building is constructed on an ashlar base and sports a brownstone belt course between the two floors. A squat wooden belltower is perched on the roof. 


Cunneen Hackett Cultural Center
9 & 12 Vassar Street

Matthew Vassar was born in England in 1792 but sailed for New York with his family four years later and settled on a farm outside Poughkeepsie. Vassar took over operations of the small family brewery when he was 18 and gradually increased capacity over the years. Vassar was one of the first brewers with national aspirations and he amassed a sizable fortune in the process. His wealth trickled down through the community, most notably in the founding of one of America’s leading women’s colleges in 1861. These two landmark Italianate buildings were developed by Vassar’s nephews, John Guy Vassar and Matthew Vassar Jr. The rambling structure at #9 was used as a home for aged men and the ornate villa at #12 performed as a museum and library, now a theater. The buildings were constructed near the site of the family’s landmark brewery.

Second Baptist Church
36 Vassar Street at Mill Street 

This Greek Revival wooden building fronted by a quartet of fluted Doric columns has served many masters since its construction in the 1830s. The first was a splinter group from the Presbyterian Church that bought it from Matthew Vassar’s family. By 1842 the First Congregational Church was meeting here. Later it was used by the local Masons and in the 1860s it was doing duty as a synagogue for the Congregated Brethren of Israel. The church design is based on a pattern in an 1833 builder’s guide; the entablature is framed by a boxed cornice, and a small round window with segmented frame is at its center.


The Italian Center
227 Mill Street 

Seeking a way to preserve and promote their Italian culture, two organizations of immigrants were formed In 1889, the “Stella D’ Italia (Star of Italy) and “The Prince of Piedmont.” The two societies merged to become “Societa Progressiva” (Progressive Society) in 1918. This picturesque Stick Style brick house was acquired as a clubhouse in 1924.


United States Post Office
55 Mansion Street at head of Market Street

You might think that between the Great Depression and World War II that Franklin Roosevelt wouldn’t have time for much else. Not so. Eric Kebbon, the government architect in charge of designing a new Poughkeepsie post office, discovered that when he submitted plans for a typical Greek Revival structure but found his sketches rejected. Seems Franklin Roosevelt had a vision for Dutchess County and that vision involved country stone and he was going to battle for it to become a reality. President Roosevelt explained why he fought so hard for the architecture of the new buildings: “We are seeking to follow the type of architecture which is good in the sense that it does not of necessity follow the whims of the moment but seeks an artistry that ought to be good, as far as we can tell, for all time to come. And we are trying to adapt the design to the historical background of the locality and to use, insofar as possible, the materials which are indigenous to the locality itself. Hence, fieldstone for Dutchess County. Hence the efforts during the past few years in Federal buildings in the Hudson River Valley to use fieldstone and to copy the early Dutch architecture which was so essentially sound besides being very attractive to the eye.” Roosevelt laid the cornerstone himself at a dedication ceremony during celebrations of the 250th anniversary of Poughkeepsie’s settlement on October 13, 1937. Five hundred workers would labor over the next two years building the 63,000-square foot post office. The final building included a lobby with murals painted by WPA artists depicting six scenes in local and state history and the Smithsonian Institution would choose it as one of ten New York post offices among the five hundred most beautiful in the country. 


Poughkeepsie Journal
85 Civic Center Plaza at Market Street 

With editions hitting the Poughkeepsie streets in 1785, the Journal stakes its claim as the oldest newspaper in New York and one of the oldest in America. It was a weekly then and did not go daily until 1860. Although it looks as if the publication may well have spent all its 225 years in this striking fieldstonebuilding, the Journal built this headquarters along the guidelines of Franklin Roosevelt’s post office across the street.  

First Baptist Church
260 Mill Street at Market Street

Poughkeepsie go-to architect James S. Post designed this red brick Gothic Revival church with a dollop of Ruskinian multi-chromatic decoration in 1875.   

Mid-Hudson Civic Center
14 Civic Center Plaza at Main and Market streets

This 1970s project was developed as an anchor for the Main Mall that operated as an outdoor pedestrian shopping plaza along Main Street. Automobile traffic as reintroduced in 2001. The Civic Center and adjacent Grand Hotel have survived the failed experiment though. The complex includes a 3,050-seat concert hall, an ice arena and an exhibition space. 


Elting Building
292 Main Street at Liberty Street

Roelof Elting, who came from Holland about the year 1660, was the patriarch for this venerable Hudson Valley family. The Elting building, with its unique mini-tower, was constructed in 1892 for Elting’s clothing store. 

Luckey, Platt & Company Department Store
southwest corner of Main and Academy streets 

Charles Luckey came from Ithaca and found work as a clerk in a small dry goods store operated by Isaac Dribble and Robert Slee. In 1866, at the age of 34, he was made a partner in the concern. Elsewhere in town, in 1863, Edmund Platt was receiving a $100,000 gift from his father for his 20th birthday. With this money, he bought into the retail business and in 1872 Charles Luckey and Edmund Platt co-founded Luckey, Platt and Co., destined to become one of the most successful department stores in the country. The emporium was an innovator in establishing a set price policy, telephone customer service, and doing business only in cash. This massive, gray, five-story Classical Revival structure was designed by Percival Lloyd and opened in 1923. The roofline features a parapet roof with a molded cornice below dancing with small lion’s heads. The frieze contains anthemion brackets, egg-and-dart and dentil moldings. Further down the facade are found pilasters with foliated capitals. Immediately adjacent on either street are older, more Italianate buildings which housed the store’s operations before the construction of the main building. Luckey, Platt & Company was shuttered in the face of competition from suburban malls in 1981 and the grand dame of retailing survived a long stretch of vacancy to be redeveloped for office space.


Lady Washington Firehouse
20 Academy Street

The Lady Washington Hose Company was created in 1863 when the city bought new fire engines for the Niagara and Cataract companies. The firehouse was built in 1908, designed in eclectic style by local architect Percival M. Lloyd. The yellow brick building sports a corbelled soffit holding a Japanese-style tiled roof and a central bay window over the garage. A castellated side tower invokes a Gothic feel. After its days as a firehouse came to an end it performed duty as a warehouse before landing on the National Register of Historic Places in 1982.

Christ Episcopal Church

20 Carroll Street at Montgomery and Academy streets

The red sandstone tower of Christ Church, designed by William Appleton Potter, is one of the best examples of 19th Century English Gothic architecture along the Hudson River. The church was erected in 1888 and the tower was added a year later. The Tudor rectory was built in 1903. This is the third meetinghouse for the congregation that organized in 1766.