Ossining - A Walk to the River
I decided to walk down to the Hudson River and have my lunch in my usual Sunday destination: The Boathouse. It was a nice day, and the Spring flowers were blooming.
Along the way I passed a number of historically significant buildings including: the Smith-Robinson house; Highland Cottage; a former Post Office; the Cynthard Building; the Olive Opera House; The First Presbyterian Church and more (which I've documented before). I also had the opportunity to take a look again at the Sing Sing Kill Greenway.
Looking down Broad Street.
The building at the center of the photograph near the river is the Smith-Robinson house. The Village of Ossining Significant Sites and Structures Guide, Page 108 has this to say about it:
Property Name: Smith-Robinson House
Other Name(s): Printex Building
Street Address: 34 State Street
Section, Block, and Lot: Section 97.07, Block 2, Lot 17
Architect/Builder: Unknown
Date of Construction: circa 1840
Architectural Style: Greek Revival (1825-1860)Greek Revival architecture came to prominence in America during the early 1800s as part of a renewed phase of interest in the architecture and culture of the ancient Mediterranean following a series of archaeological discoveries in the late 18th century. Greek Revival structures are often identifiable by the use of a temple front façade configuration, with a large triangular pediment and columns dominating the main façade. Some examples of the style may utilize the columns without the pediment, while others may have an appearance consisting of a blend of Greek temple features with other early 19th century styles.
The Smith-Robinson House is two stories in height, five bays wide, and five bays deep. A veranda with six one story Doric columns extends along the length of the main façade, along with a second story balustrade and balcony above. A raised basement story is visible below the veranda, and the original windows on this story of the structure were enclosed at an unknown date. The window configuration on the main façade consists of six over six wood sash double hung windows with stone sills and lintels. The main entryway has a transom window over the door and is flanked by side lights. The house is also architecturally notable for one of the most complete and well-preserved Greek Revival interiors in Westchester County. The building has a flat roof and is built from Sing Sing Marble.
Significance: Architectural and Cultural
The Smith-Robinson House is architecturally significant as one of three remaining Greek Revival structures in the Village of Ossining. The others are neighboring James Robinson House (see entry) and the Charles Snowden House, (see entry). It is also culturally significant for its association with James Robinson and James Smith, two wealthy mid 19th century Sing Sing Village landowners.
Narrative:
The Smith Robinson House, located at 34 State Street and built in the 1840’s, was constructed by a local businessman named James Smith as his residence. The original estate on which the house was built once extended east all the way to Highland Avenue and contained several acres worth of orchards. The property was later purchased by James Robinson, another wealthy local landowner who built the residence that bears his name in 1860. The house was used as a wallpaper factory for a time in the 1940s, in 1948 the house served as offices for the Printex Corporation, a now-defunct textile manufacturer. An expansion wing built in a utilitarian style was constructed in 1955, and a dedicated factory facility was built on the south side of the house in 1967. The house has had a series of owners and tenants since then and was used as a meeting space for the Catholic Community Club, Knights of Columbus and other nonprofit organizations for a time. Currently, it is vacant and unused but retains much of its original condition.
I took this photograph from Highland Ave., so everything you see would once have been part of the estate. A friend who’s quite knowledgeable about the history of Ossining (he’s even written a book about it) informs me that Broad Ave. was once the road to the main entrance of the Smith-Robinson House.
As mentioned above the Guide, which was published in April 2010, states “Currently, it is vacant and unused but retains most of its original condition”. This photograph was taken March 29, 2025, and you can see that much still needs to be done.
Trimming trees in Ossining
I imagine he had a wonderful view of the Hudson River with the Palisades and High Tor park in the background.
Two Dogs
I came across these two dogs during my walk. I don’t think they liked me.
The first one was the most aggressive, barking almost continuously.
The second one was more tentative. I think he felt that he had to support his friend, but his heart wasn’t really in it. He’d probably have been happier playing catch.
There was also a third dog, but he didn’t want to be associated with the other two and immediately took off inside the house, preventing me from taking a picture.
Highland Cottage.
Property Name: Highland Cottage
Other Name(s): Squire House, Squire School, Mud House
Street Address: 36 South Highland Avenue
Section, Block, and Lot: Section 89.19, Block 4, Lot 67
Architect/Builder: S. Marvin McCord, Architect
Date of Construction: 1872
Architectural Style: High Victorian Gothic (1860s-1890s)High Victorian Gothic architecture, which evolved from the Gothic Revival style, differs from that style in its use of contrasting polychromatic bands on the exterior wall surfaces and more elaborate decorative elements. This style was usually reserved for public buildings such as schools or churches. As it is related to the Gothic Revival architecture, structures in this style also contain such elements as steeply pitched rooflines, elaborate ornamentation, and a predominantly vertical orientation.
Highland Cottage is a rare application of the High Victorian Gothic style in a private home. The structure is two stories tall and three bays wide. The exterior is defined by its irregular massing and rooflines; the structure contains a tall, pyramidal roofed central tower and a shorter, mansard roof southern section contains a turreted dormer window on the roof and a large bay window on the first floor of the main façade. The one story northern wing contains a mansard roof and a porch extending along the main façade. The steeply pitched gables, the most prominent of which is located above the main entryway, are cast in Sing Sing marble. The most striking architectural feature of Highland Cottage is its concrete construction. The exterior walls are made of 18-inch-thick concrete, covered with a layer of stucco that was scored in a fashion that lends the appearance of stone blocks. The house’s doors are solid walnut, as is its trim. The detailed and elaborate exterior ornamentation is mostly concrete and was cast in specially designed molds.
Significance: Architectural and Cultural
Highland Cottage was added to the National Register of Historic Places in 1982. It is architecturally significant as one of the earliest surviving concrete houses in Westchester County and the only such house within Ossining. It is also culturally significant for its association with Henry J. Baker, Amos O. Squire and his daughter Evelyn Squire Culp, each of whom played an important role in Ossining’s civic life in the 19th and 20th centuries.
Narrative:
Highland Cottage, also known by the name Squire House, is a High Victorian Gothic style cottage constructed in 1872 by late 19th century financier Henry J. Baker (1818-1878), a New York City businessman who moved to Ossining. The house was built almost entirely from concrete, leading to the disparaging nickname “Mud House”. Workers experienced in the use of concrete in house construction were brought to Ossining from England to build the house, as concrete has always been rarely used in house construction in the United States due to the long-time availability of wood and brick masonry as construction materials in the United States. The cement used to form the walls was mined and processed in the Town of Rosendale in Ulster County, New York, the site of one the largest cement manufactories in the United States at the time.
Amos Osborne Squire (1876-1949), the most famous resident of the house, operated a private mental hospital called the Grandview Sanitarium inside Highland Cottage. Squire later became chief physician at Sing Sing Prison during the early 1900s and served as the medical examiner for Westchester County for twenty-three years and as the Village’s health officer during the 1920s. Squire’s daughter Evelyn Squire Culp (1907-2002), who was named Ossining Woman of the Year in 1970, played an important role in the civic life of Ossining during the mid 20th century in such organizations as the Ossining Historical Society, the Ossining Women’s Club, and the Ossining Garden Club, among others. Culp also ran the Squire School of Business at the house from 1952 to 1984 and taught office skills such as typing, shorthand, and other secretarial skills.
Culp donated the house to Westchester Preservation League in 1984 and continued to live in the house until 1996. The Preservation League later sold the house to a private owner.
Village of Ossining Significant Sites and Structures Guide, page 158.
Daffodils
I always thought that the name of the famous poem by Wordsworth was “Daffodils”, but apparently it’s actually “I Wandered Lonely as a Cloud”. I prefer “Daffodils”.
Here’s the poem:
I wandered lonely as a cloud
That floats on high o’er vales and hills,
When all at once I saw a crowd,
A host, of golden daffodils;
Beside the lake, beneath the trees,
Fluttering and dancing in the breeze.Continuous as the stars that shine
And twinkle on the milky way,
They stretched in never-ending line
Along the margin of a bay:
Ten thousand saw I at a glance,
Tossing their heads in sprightly dance.The waves beside them danced; but they
Out-did the sparkling waves in glee:
A poet could not but be gay,
In such a jocund company:
I gazed—and gazed—but little thought
What wealth the show to me had brought:For oft, when on my couch I lie
In vacant or in pensive mood,
They flash upon that inward eye
Which is the bliss of solitude;
And then my heart with pleasure fills,
And dances with the daffodils.
I didn’t have quite the experience that Wordsworth had:
I was in a suburban New York town, so I didn’t see “…a crowd, a host of golden daffodils”, just the few that you see in the pictures.
I wasn’t “beside the lake, beneath the trees” although I was quite close to the Hudson River.
The daffodils were not “fluttering and dancing in the breeze”.
There certainly weren’t “ten thousand” of them.
Still, I very much agree with the sentiments expressed in the final verse.
Not a Post Office
Despite what it says over the door this is not a PostO ffice. Although It clearly bears the words “US Post Office, Ossining, NY” over the door, but it is no longer the Ossining Post Office, even though it once was. Nowadays, the left part of the building is a hairdresser, and the right part a doctor’s office.
As the Great Depression set in and construction slowed, one more public building completed the Downtown Historic District. The post office had outgrown its space at the Barlow Block again and needed to move. As part of the national relief programs, many new post offices were built. Arthur Ware contributed a restrained Classical Revival one-story brick building on South Highland, between the Cynthard Building and the Presbyterian Church, on the site of what had been the last remaining house on the west side of Main in the district. It was completed in 1933, the newest contributing property in the district.
As the 20th century became the 21st. The post office moved out of this building for a newer facility on the south side of Main Street, in the space cleared three decades earlier by urban renewal opposite the western extent of the district. Its former building (this one) was converted to retail use.
The Cynthard Building
Property Name: Cynthard Building
Street Address: 26 South Highland Avenue
Section, Block, and Lot: Section 89.19, Block 4, Lot 50
Historic District: Downtown Ossining Historic District
Architect/Builder: Unknown.
Date of Construction: 1929
Architectural Style: Renaissance Revival (1890-1935)The Renaissance Revival architecture of the last decade of the 19th century and early years of the 20th century represented a new wave of interest in the classical forms of renaissance-era Italy. This style, which was more faithful to the original Italian designs than the preceding Italianate (1840-1885) style, typically utilized low-pitched clay tile roofs, arched window openings and entryways, and bracketed eaves and employed a symmetrical aesthetic in the design configuration.
The Cynthard Building is one story in height, four and one half bays wide, and two and one half bays deep. The structure’s most prominent exterior feature is the two-part cornice extending across the upper facing of both the Main Street and Church Street façades. The upper part of the cornice features a repeating motif consisting of a pair of seahorses, while the lower portion has a series of repeating Mediterranean arches with a lion’s head at the base of each arch. The northeast corner contains a pediment with a decorative motif called a swan’s neck pediment, a type of design in which the pediment is open in the middle and is flanked by two S-shaped curved pieces. The pediment also contains a coat of arms in its center with Classical-style urns. The structure has a flat roof and is constructed with terra cotta.
Significance: Historical and Architectural
The Cynthard Building is historically significant as the site of the former Union Hotel, which stood in this location from 1800 to 1890. It is also architecturally significant for the original classical-styled features on the façade, which have been preserved in good condition since its construction in 1929. The building is listed as a contributing structure within the Village’s National Register of Historic Places-listed Downtown Historic District.
Narrative: The Cynthard Building, constructed in 1929 and located at the corner of Main Street and Church Street, is a commercial structure consisting of retail storefronts for small businesses. This site was originally the home of the Union Hotel, a popular stopover on the Old Albany Post Road during the 19th Century. The Hotel was in operation from approximately 1800 to 1890. Following the demolition of the hotel, the site was subdivided and a Romanesque-Revival masonry structure that served as the offices for a local doctor named William Sherwood stood on the northern portion of the site, where the Cynthard Building now resides. This structure was demolished during the first decades of the 20th century. The southern portion of the site was first home to a large Victorian home until the former Ossining Post Office (see entry) was built on the site in 1935. On March 14th, 2003, a a fire damaged the Cynthard Building, causing its closure for repair and restoration until 2006.
Village of Ossining Significant Sites and Structures Guide, page 213.
Hudson Valley Books For Humanity and more
This fairly nondescript building houses one of my favorite places in Ossining, the above-mentioned bookstore. When I walk down to the river I usually stop there for a while. It’s a very comfortable place with plush chairs and sofas. The people are very friendly, and their collection of new and used books is impressive. Most importantly, perhaps is that it is nice to have an independent bookstore that I can walk to from my house.
The building that houses the bookstore has an interesting history:
Property Name: Olive Opera House
Street Address: 63-67 Central Avenue
Section, Block, and Lot: Section 89.19, Block 5, Lot 63
Historic District: Downtown Ossining Historic District
Architect/Builder: Unknown
Date of Construction: 1865
Architectural Style: Second Empire (1860s-1880s) with substantial alterationsSecond Empire-style architecture was a style that originated in France and was named for Napoleon III’s campaign to modernize Paris in the mid 19th Century. This style, which is similar to the Italianate style, utilizes elements such as tall, arched window openings, columns flanking the main entryway, and cornices below the roofline. The primary distinguishing characteristic is the Mansard roof, a configuration in which the roof has a steep pitch on the lower section and a shallower pitch on the upper portion.
The Olive Opera House is a rectangular shaped structure three stories in height, three bays wide, and eight bays in depth. The building has been significantly altered from its original 1865 105 Village of Ossining Significant Sites and Structures Guide appearance. The original Mansard roof was replaced with a hipped roof with a bracketed cornice following damage sustained in the Ossining fire of 1872. The main façade of the Opera House was substantially altered twice: Once following the 1872 fire and again following the building’s adaptation for commercial use in 1922. The arrangement of windows on both the ground floor and upper stories of the main façade were reconfigured, with the original segmentally arched lintels and stone sills removed. Six of the original windows located on the east façade facing Brandreth Street remain. The current configuration of windows consists of a mix of casement and sash windows, with tall second story windows with stone sills on the main façade. The east elevation contains tall second story windows with arched openings and stone sills. The decorative metal pilasters on the first floor of the main façade are a remnant of the building’s original appearance. Overall, the building’s current appearance reflects the utilitarian adaptations made to it for commercial use once the original opera house closed down in 1922.
Significance: Historical
The Olive Opera House is National-Register listed as a contributing structure within the Downtown Ossining Historic District. Its significance stems from its importance to the community life of 19th and early 20th Century Ossining as the premier site for entertainment and the arts in Downtown Ossining.
Narrative:
The Olive Opera House, located at the intersection of Central Avenue, Brandreth Street, and Main Street, served as the prime entertainment center for downtown Ossining from its opening in 1862 until its closure in 1922. In the 19th century, the term “opera house” referred to a multi- purpose space designed to serve as the locus of entertainment and the arts in a community. The 1872 fire that destroyed the Barlow Block also severely damaged the Opera House, and at that time it was almost completely rebuilt, and it continued to serve as an entertainment destination for another fifty years. In 1922, the opera house closed down and the building became a factory for the Steward Manufacturing Corporation. Today, the site serves as a workspace for local artists.
Village of Ossining Significant Sites and Structures Guide, page 105.
Unusual doorway to the Ossining First Presbyterian Church
Property Name: First Presbyterian Church
Street Address: 34 South Highland Avenue
Section, Block, and Lot: Section 89.19, Block 4, Lot 52
Historic District: Downtown Ossining Historic District
Architect/Builder: Isaac Gale Perry, Architect; Peter H. Terhune, Contractor.
Date of Construction: 1870
Architectural Style: High Victorian Gothic (1860s-1890s)High Victorian Gothic architecture, which evolved from the older Gothic Revival style, differs from that style in its use of contrasting polychromatic bands on the exterior wall surfaces and more elaborate decorative elements. This style was usually reserved for public buildings such as schools or churches. As it is related to the Gothic Revival architecture, structures in this style also contain such elements as steeply pitched rooflines, elaborate ornamentation, and a predominantly vertical orientation.
The First Presbyterian Church is two stories in height with rectangular massing. The front façade is dominated by two front towers on either side of the main entryway. Typical of the High Victorian Gothic style, the church makes use of the polychrome theme with the contrasting brick colors on window sills, lintels, surrounds, buttress caps, and surrounding the main entrance. The gothic pointed arch motif is used for window openings and entryways. The gabled main entrance, which faces South Highland Avenue, is surrounded with elaborate limestone work. The church originally was constructed with a tall steeple on the southeast tower that was subsequently removed in the 1950s when the building was renovated and modernized. The church is constructed with brick and limestone.
Significance: Architectural and Cultural
The First Presbyterian Church is National Register-listed as a contributing structure within the Downtown Ossining Historic District. It is architecturally significant as a well preserved example of High Victorian Gothic architecture within Ossining. Other structures of this style include the First Baptist Church (see entry) and the First Presbyterian Church (see entry). This structure is also culturally significant as the home of the First Presbyterian Congregation of Ossining.
Narrative:
The First Presbyterian Congregation was formed in 1763 and originally occupied a site located in what is now Sparta Cemetery on land donated by Frederick Phillipse, owner of the vast Phillipse Estate that stretched from modern-day Kingsbridge, Bronx to the Croton River. The original building was damaged during the Revolutionary War, prompting the congregation to build a new structure in the village of Sing Sing on the site of the current Trinity Episcopal Church at 7 South Highland Avenue in 1803. As the congregation grew, this church was expanded until it was no longer adequate to house all those who wished to worship there. The present church was constructed from 1868 to 1870 for a cost of approximately $95,000 by contractor Peter H. Terhune of Binghamton, NY and designed by architect Isaac Gale Perry. Perry was later appointed as the State Architect for the State of New York and designed the final phase of the New York State Capitol in Albany from 1883 to 1899 as well as the New York State Armory in Poughkeepsie in 1891.
Village of Ossining Significant Sites and Structures Guide, page 196.
Sing Sing Kill Greenway
Ossining’s Sing Sing Kill Greenway is a concrete walkway opened in 2016 that runs down the Sing Sing Kill gorge. It’s a unique experience walking down the gorge with steep hills on either side of you and the brook beneath you. You’re practically in the middle of Ossining’s Old Village, but in a different world.
The “main” entrance is adjacent to the lower parking lot at the Ossining Community Center at 95 Broadway. The walkway runs about 1/3 of a mile down the gorge and ends up on Central Ave. If you parked at the community center then at that point you either turn around and go back up the gorge, or you can take the longer route up to Main St, take a left onto the Croton Aqueduct Trailway then head back down to the Community Center.
The greenway has some wonderful views of Ossining’s famous Double Arch Bridge
My final destination
So, I finally got to my final destination: The Boathouse, right on the Hudson River. I generally go there for Sunday lunch. To me it feels like a little piece of New England.