National Register Historic District

Trowbridge Square

Portsea Street

Portsea Street

The Trowbridge Square Historic District is New Haven’s most intact and cohesive example of a 19th century working-class residential. Roughly bounded by Columbus and Howard Avenues, Loop Road, Liberty Street, and the railroad tracks, the district is historically significant for its association with Simeon Jocelyn, one of New Haven’s foremost social reformers and real estate developers of the antebellum era. The district is architecturally noteworthy for its concentration of well-preserved modest houses, that illustrate the development of working-class residential architecture during the late 19th century.

The area in which the district lies had an unsavory reputation in the early decades of the 19th century. Separated from the city by the salt marshes of the West Creek (whose course is now marked by Route 34, the Oak Street Connector) and bordering on docks and tanneries, it was one of the shanty settlements that grew up on the fringes of town. At the turn of the 19th century, the high ground along Columbus Avenue was known as Sodom Hill. By 1812, development was contemplated. A map of that date shows a grid of streets laid out in the form of two large squares delineated by Howard Avenue, Columbus Avenue, Putnam, and Water Streets, each square similar in size to one of the nine squares of the city. The area is labeled “Oyster Point Quarter.” It is known that James Hillhouse owned a great deal of land in the Oyster Point Quarter which he was attempting to develop. It is also known that Hillhouse was concerned with ensuring an orderly growth of the expanding city and perpetuating the grid of the nine squares beyond its original limits. It seems highly likely that the initial blocking out of the neighborhood was strongly influenced by him. The project, however, was premature. The depression of 1807-25 intervened, temporarily arresting the city’s expansion, and little new building took place.

The modern history of the district dates from 1830. In that year, Simeon Jocelyn formed a business partnership with local builder/architect Isaac Thompson. The men purchased slightly more than 15 acres of developed land in the district; laid out Portsea, Carlisle, Putnam, Salem, and Liberty Streets; and sub-divided the majority of land along these new streets into small building lots. The layout of this subdivision, which the men christened “the Village of Spireworth,” was designed as a miniature version of New Haven’s original nine-square settlement plat. Like its model, the central square of the village (“Spireworth Square”) was reserved for use as an open public place. The project as a whole, which included Howard Avenue, was typical of the vertically integrated neighborhoods of the 19th century.

A native resident of New Haven, Simeon Jocelyn (1799-1879) was a Congregational minister who was strongly influenced by the era’s liberal gospel of responsibility, that charged the more fortunate members of society with the duty of educating, uplifting, and maintaining the poor, ignorant, and disadvantaged. Jocelyn’s subscription to this philosophy led him to become one of the city’s most active and outspoken proponents of temperance and abolition. For example, as a means of providing for the “spiritual betterment” of the city’s black population, he helped organize a black church known as the United African Society in 1820, and officiated at church services and related functions for the ensuring 14 years. In conjunction with several like-minded men, including his brother, the noted artist and engraver Nathaniel Jocelyn, Simeon spearheaded an unsuccessful attempt to establish a “college for colored people” in New Haven in 1831. During the antebellum years, he also emerged as a leading spokesman for the American Anti-Slavery Society, an organization which he helped found in 1833.

Like many prominent men of his era, Jocelyn was also active as a businessman and real estate speculator/developer. In cooperation with his brother, he operated a highly successful engraving firm in the city. The profits generated by this firm enabled Jocelyn to embark upon a number of real estate ventures throughout the city during the 1820s and 1830s; these ventures included the 40- acre Franklin Square subdivision in the eastern portion of the city, one of the largest planned subdivisions laid out in New Haven in the 19th century.

While the Village of Spireworth was not the largest real estate project initiated by Jocelyn, it proved to be the most significant of his ventures. It was the only project in which Jocelyn is known to have activity attempted to combine his passion for real estate speculation with the moral imperatives embodied in the gospel of responsibility. Jocelyn’s desire to establish and develop the village as a harmonious community in which the city’s poor and disadvantaged could achieve spiritual, moral, and economic “betterment” was reflected in the very choice of the new village’s name, which “… alluded to a slender spindling sort of grass that grows only in the poor soil.” It was also reflected in restrictive covenants placed in deeds granted for lots in the village during the 1830s and 1840s, which stipulated that no “ardent spirits” could be sold on the property, that the property could never be sold or rented to persons of “disreputable character,” and, in some cases, that sale or rental of the property to “colored” individuals would not be refused solely on that basis. The settlement of the blacks in the village during the 1830s and early 1840s was further encouraged by the construction and transfer of title for a small school (no longer extant) on Carlisle Street to members of the village’s growing black population, and the donation in 1834 of a lot on Salem Street opposite the square to these same individuals “solely for the erection of a House of Worship.”

By the mid-1830s, a number of property owners who held land abutting the eastern and southern sides of the village (such as Henry Hotchkins, who owned and operated a ropewalk slightly south of Putnam Street) began extending village roads through their properties and subdividing their land for sale as small building lots. While most deeds granted for these new lots specify their location as “Mount Pleasant” rather than “Spireworth,” from a social, economic, and architectural standpoint, by the mid- 1840s the blocks lying immediately east and south of the village’s original nine squares were beginning to emerge as integral components of a still lightly populated, but nonetheless physically expanding, low-income neighborhood. For example, the 1845-46 New Haven City Directory lists 66 individuals living in the area. Of these individuals, about half were occupying two dozen small frame houses built within the village’s original nine squares; extant examples of these houses include 154, 158, 169 Cedar Street, 66 and 68 Liberty Street, and 168 and 172 Portsea Street. The remaining half lived in similarly modest frame houses built in the blocks along the fringe of the village core, such as the range of houses erected between 1838 and 1845 for Elijah Prindle along the southern side of Portsea Street, east of Liberty Street. This city directory also indicates that virtually all of those living in the area were employed as common laborers performing menial tasks. By this time that area’s population was predominantly black (58%), but blacks and whites were thoroughly integrated in terms of residential location within the district.

Despite the activities of Jocelyn and his brother Nathaniel, and developers such as Prindle and Hotchkiss, by 1851 less than 50 houses had been built within in the expanded village area. The reasons for the limited development are still not fully understood; it may have been due in some measure to the severe depression of the real estate market accompanying the financial panics which swept the nation in 1837 and 1839. Having made extensive investments in local real estate ventures in the years immediately preceding these panics, developers such as the Jocelyns found themselves financially over-extended by the early 1840s and, unable to recover, bankrupted shortly thereafter.

By the early 1850s other speculators and developers had acquired most of the still-substantial portions of undeveloped land at Spireworth/Mount Pleasant. The most significant of these were members of the Trowbridge family, who had owned large tracts of land along the harborfront since the Colonial era, and Gerard Hallock. Thomas Trowbridge and Gerard Hallock spearheaded the construction of the South Congregational Church on the northwestern corner of Liberty Street and Columbus Avenue in 1851; they also appear to have provided the wherewithal to make improvements to the district’s square, such as the erection of the extant granite and cast-iron frence, about this same time. While Hallock engaged in some speculative housing construction and sold lots in the southern portion of the district to small-scale builder/developers over the ensuring decades, it was Thomas Trowbridge and other members of his family who promoted the district’s speculative development between the 1850s and the 1890s, a fact reflected by the renaming of the district’s square for the family in the 1880s.

The Trowbridge family’s involvement in the development of the area after 1850 appears to have been motivated by financial investment and gain. However, their work over the course of the remaining decades of the century did follow the area’s early development pattern in at least one major respect—virtually all of the houses which the Trowbridges built during this period were designed for sale or rental to members of the city’s growing lower-income, working-class population.

The Trowbridge family was responsible for the construction of a high number of the small worker’s cottages built around and near the square during the second half of the 19th century. For example, in the 1850s, the family had a range of small dwellings constructed along Carlisle Street opposite the square; they had the northern side of Portsea Street opposite the square built up in the 1860s; during the 1870s they built the groups of small cottages lining Salem Street at the square’s western end and along southern side of Carlisle Street just east of the square; and in the 1880s, the family built the small Queen Anna-style cottages on Cedar Street facing the eastern end of the square.

By the mid-1860s, the Trowbridge family and Gerard Hallock had also begun to sell off some of their holdings in the district to local developers, the most significant and active of whom was Andrew C. Smith. Smith’s initial involvement in the area seems to have been as a builder; he appears to have constructed a number of the houses erected for the Trowbridges in the early 1860s. By the late 1860s, Smith had purchased most of the land lying along both sides of Cedar Street between Putnam and Spring Streets from the Trowbridges and Hallock, as well as a number of other scattered lots throughout the district. On most of these lots, he erected Italianate-style houses with low-hip or gable-to-street roofs. While somewhat larger and featuring slightly more elaborate exterior details than the workers cottages built in the area, Smith’s houses nonetheless exhibit a modesty of scale and design typically associated with 19th-century worker housing.

The continuing growth and development of the district as a working-class residential locus from the 1860s through the end of the 19th century was associated with the concurrent development and expansion of the New York, New Haven, and Hartford Railroad. In the 1860s, the railroad erected major repair and terminal facilities along the mud flats of the city’s harbor, which lay adjacent to the eastern side of the district. The construction and expansion of these facilities over the ensuring decades fostered an ever-increasing need for unskilled, semi-skilled, and skilled labor, which created a constantly growing demand for cheap housing in the area.

As in other growing industries in New Haven during the second half of the 19th century, the railroad’s principal source for unskilled and semi-skilled labor was the city’s growing population of Irish immigrants. By the mid-1870s, Trowbridge Square and its environs developed into one of the city’s principal lower-income Irish working-class neighborhoods. The district’s emergence as a predominantly Irish area was tangibly reflected by the purchase and conversion of the 1851 South Congregational Church in 1875 by the district’s Irish Roman Catholics for use as the Church of the Sacred Heart.

The district’s growth and consolidation as an Irish working-class neighborhood continued through the earliest years of the 20th century. Throughout most of the district, new construction was limited to erecting infill structures, such as the few multi-unit brick apartment buildings and frame tenements erected along Columbus Avenue just west of Salem Street (232-34, 246, 248 and 258-60 Columbus Avenue) and Portsea and upper Salem Streets (223-25 Portsea Street, 47-49, 48-50, and 52-54 Salem Street) in the late 1880s and 1890s. The only significant redevelopment of sites to have occurred prior to the 20th century was located in the block framed by Columbus Avenue and Liberty, Portsea and Cedar Streets, where the parishioners of the Church of the Sacred Heart demolished a group of the 19th century frame structures before erecting school, convent, and rectory buildings in the mid-1890s. During these latter decades of the 19th century, developers built houses for sale or rental along Rosette Street. Laid out in the 1880s, Rosette Street was the last street opened in the district. Located just north of the railroad culvert which forms the district’s southernmost boundary, and lined with small modest Stick-style and Queen Anne/Colonial Revival-style cottages, this street formed the southernmost terminus of concentrated residential development in the Trowbridge Square district prior to the turn of the 20th century. The overall physical character of the district experienced relatively few changes in the early 20th century. The most significant of these changes was the demolition of roughly 16 houses, including a group of small workers’ cottages erected for the Trowbridges across from the southern end of the square in the 1850s; these cottages were replaced in 1925 by the Trowbridge Recreation Center, a brick Neo-Classical-style structure designed by the locally prominent architectural firm of Brown and Von Beren.

During the early 20th century, the principal ethnic background of the district’s population began to shift. As members of the area’s upwardly mobile Irish-American population began to move out of the expanding middle-class “streetcar suburbs” along the city’s northern and western fringes, they were increasingly replaced by Italian immigrant families. City directories indicate that by the onset of World War II, the district’s population was dominated by Italian-American workers and their families. Following World War II, the ethnic character of the neighborhood began to shift again. As more and more of the districts Italian-Americans moved to developing suburban areas in adjacent towns, the district began to experience an influx of black and Hispanic families.

The district derives the distinctive architectural character primarily from its retention of well-preserved streetscapes comprised of extremely small and modestly scaled, Victorian residences built over the course of six decades for members of the city’s working-class population. Encompassing a relatively complete range of popular vernacular residential building styles and forms from this era, the houses that dominate these streetscapes not only continue to reflect the area’s historic development, they also serve as one of the city’s most comprehensive catalogues of 19th-century vernacular house types.

The Trowbridge Square Historic District was listed in the National Register of Historic Places on September 12, 1985.


Explore New Haven’s historic districts HERE