Middletown Upper Houses Historic District

Cromwell Town, Middlesex County, CT

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The Middletown Upper Houses Historic District was listed on the National Register of Historic Places in 1979. Portions of the content on this web page were adapted from a copy of the original nomination document. [1]


The Middletown Upper Houses Historic District (also known as Upper Houses River Port) is a small, relatively isolated, residential area located on the banks of the Connecticut River in the southeastern section of Cromwell. The Middletown Upper Houses Historic District consists of five streets which formed the nucleus of 18th century Cromwell, or Upper Houses of Middletown, and contains a concentration of buildings dating from the 18th and early 19th centuries. The area is bounded on the east by the Connecticut River, on the north and south by marshland, and on the west by Main Street (Route 9A).

The Middletown Upper Houses Historic District is residential in character. Houses from the 18th and early-19th centuries predominate; late-19th century and 20th century buildings are integrated into the community. There are 72 houses in the Middletown Upper Houses Historic District (Upper Houses River Port Historic District); nearly half predate 1810. The distribution is as follows: Center-Chimney Colonial (1700-1800), 14; Federal (1790-1810), 14; Greek Revival or Italianate (1820-1870), 7; Victorian (1870-1900), 15; Early 20th century (1900-1940), 7; 1940 to Present, 15.

Three barns, a brick smokehouse, garages and sheds, one large commercial building, and the remains of a brownstone loading dock are also included in the Middletown Upper Houses Historic District.

The Middletown Upper Houses Historic District is located on the relatively flat flood plain of the Connecticut River. Houses are primarily of 2 or 2-1/2 stories, frame, and modest in scale. They are sited on medium sized lots, with consistent setbacks from the streets, creating a relatively uniform scale throughout the district. There are no sidewalks, and plantings and landscaping tends to be informal.

The Middletown Upper Houses Historic District consists of five streets. River Road (following closely by the Connecticut River) and Pleasant Street run north and south. Wall, School, and South Streets cross on an east-west axis, with Wall and South Streets joining to Main Street on the west. This group of streets formed the center of 18th century Cromwell (settled ca.1651). A typical New England centralized agricultural village, Upper Houses entered a period of mercantile prosperity in the late 18th and early 19th centuries. During this period, the Middletown Upper Houses Historic District was the center of town, and included stores and artisans' shops on the banks of the river. The residences of merchants, sea captains, craftsmen, and farmers constructed during this prosperous era constitute a significant number of buildings surviving today. A brownstone loading dock is located on the river just north of Wall Street; at least one group of docks and warehouses were sited on the river bank at the foot of South Street.

Buildings dating between 1750 and 1810 are visually dominant in the area. The most common type of structure is the center-chimney framed house of two stories. Many display a single or double overhang. They vary in size: a number of houses on the north side of Wall Street are quite small (average 26'x30'); others such as 16 South Street and 45 River Road are large (about 30'x36'). The second most common type is that commonly called a "half house," displaying a three-bay facade with a side hall, the ridge of the roof parallel to the street, and an off-center chimney.

The architectural quality of buildings from this period (1756-1810) varies throughout the district. Although most are now covered with later siding, many display decorative features typical of the era. Modillioned or denticulated cornices and molded window caps are common. A number of doorways are of special interest, including the two doorways with fanlights on the Captain Ralph Hubbard House at 8 South Street, and the matching doorways on the Federal style houses at 6 and 10 School Street. Smoothly dressed brownstone ashlar laid without mortar is common for foundations, especially on facades.

Buildings dating from 1750 to 1810 set the general tone and character of the Middletown Upper Houses Historic District. Throughout the area are small concentrations of buildings which are particularly evocative of the sense and appearance of 18th century Upper Houses. These include, for example, four houses closely sited on the north side of Wall Street (#s 17, 21, 23, and 25), and four houses lined on the west side of River Road with a vista across the river to the east (#s 37, 39, 41, and 45). The two matching Federal houses on the north side of School Street (#s 6 and 10) and Bell Schoolhouse on the south side, were the first and only buildings constructed on the street. The scale and siting of these early streetscapes make a significant contribution to the historic character of the district.

By the 1820s, river trade declined, and although Upper Houses remained important in the life of the town, residential development in mid-19th century Cromwell (so named after achieving independence from Middletown in 1851) occurred primarily on Main Street to the north. The Middletown Upper Houses Historic District contains few houses of this period in the Greek Revival or Italianate styles. During this time, commercial development also began to center on Main Street just northwest of the boundaries of the Middletown Upper Houses Historic District, in what is now the center of town.

Between 1870 and 1900 some residential development occurred in the area, stimulated by quarrying and industrial activities in the town. Scattered throughout the Upper Houses River Port area are modest frame houses of very plain design, Victorian cottages of L-shaped form with cross-gable roofs and side porches, and a few larger houses of the Queen Anne style. Residential development continued sporadically in the 20th century, and consisted primarily of small frame houses either Colonial Revival in spirit or the post-World War II Ranch type.

Presently, the Middletown Upper Houses Historic District (Upper Houses River Port Historic District) contains a mixture of buildings; those of the earliest period are dominant. These early buildings set the general character of the district, and the setting and street layout maintain a traditional feeling. In general, later structures maintain the scale and siting of earlier buildings, and do not detract from the historic area as a whole.

Many of the buildings in the Middletown Upper Houses Historic District have suffered from neglect and unsympathetic alterations in recent years. Asphalt or asbestos shingles and aluminum siding have been applied to most of the pre-1900 structures. Most of the alterations, however, are of a reversible character, and the trend of recent activity in the district has been toward restoration of the historic character of individual buildings. The major non-conforming intrusion in the district is the Connecticut Hardware Supply Company, a large two-story concrete building on River Road.

The Middletown Upper Houses Historic District as a whole has a quiet residential character and a pedestrian scale. It is visually and functionally isolated from the rest of the town. Traffic and commercial activity is concentrated on Main Street (Route 9A) to the west. Wetlands and marsh on the south and north contribute to the secluded, slightly pastoral sense. The dominant natural feature, and a critical visual element of the Middletown Upper Houses Historic District, is the Connecticut River which affords a splendid vista of the gradually rising hills of Portland to the east.


The Upper Houses River Port National Register Historic District in Cromwell, Connecticut is a significant and distinguishable entity which illustrates the earliest periods of development in the Connecticut River Valley: the settlement of the valley through centralized villages primarily engaged in agriculture; and the commercial activity connected with sea trade which transformed these early communities into mercantile towns. The area contains a significant collection of 18th and early 19th century buildings. Although exhibiting some residential development from the late-19th and 20th centuries, the siting, scale, street placement and setting of the area are representative of the primary period of significance. The Middletown Upper Houses Historic District continues to maintain its integrity as a unit because of the isolating effect of those features which also enhance its setting: the Connecticut, River to the east, meadows to north and south, and Main Street to the west.

The streets which formed the nucleus of 17th and 18th century Cromwell comprise the Upper Houses River Port National Register Historic District. Mattabeseck (a tract of land 16 miles by 9 miles square encompassing the present towns of Middletown, Cromwell, Middlefield, Portland and East Hampton) was first, settled in 1650 or 1651 at places north and south of the "riverett" or Little River. These early settlements later became the towns of Cromwell and Middletown. Pleasant Street, in "Upper Middletown" or "Upper Houses," was laid out on slightly elevated ground on the fertile flood plain of the Connecticut River. It was just above the meadows and the Little River which separated the "Upper Houses" from the "Lower Houses," and became the backbone of a nucleated agricultural village typical of the period. Home lots were granted on either side of the street, and outlying lands were distributed as surveyed and needed. South Street and River Road south of South Street were laid soon after, and together with Pleasant Street and upper Main Street formed part of the highway which ran from lower to upper Middletown and continued to Wethersfield. By 1670 there were eleven proprietors and their families residing north of the Little River. By 1703 the population at Upper Houses had reached approximately 250, and was granted permission to form a separate parish, the North or Second Ecclesiastical Society of Middletown.

By the middle of the eighteenth century, Upper Houses, like many other Connecticut River towns, began to participate in the mercantile activity, which transformed its social and economic life. The West Indies and coasting trade brought prosperity and economic development to the village. By mid-eighteenth century there was at least one ship-building yard in Upper Houses, and a house constructed by the Stocking family. By the 1770s there were at least three shipyards, and a number of wharves and warehouses were located on the river, near the ends of Wall and South Streets.

By the beginning of the 19th century, the Upper Houses river port area had become a thriving, albeit small-scale, seaport. It was the center of Upper Middletown, and teemed with commercial enterprises and activity on the riverbanks. New streets had been developed from the original 17th century nucleated settlement. Wall Street (Freestone Avenue) had been laid probably early in the eighteenth century. By 1795 River Road was extended from South Street to Wall Street and further north, providing greater access to the wharves and warehouses there. School Street was laid out in 1803. Original home lots were divided and new residences built for merchants, sea captains, craftsmen and farmers.

Dr. Dwight, in his Travels Through New England, described Upper Houses in 1796: "The Village which bears this name and contains a considerable part of the inhabitants, is a thrifty settlement on the southern declivity of a beautiful hill... The houses, about 80 in number, are generally well built, and the whole place wears an air of sprightliness and prosperity. An advantageous trade was carried on by the inhabitants, particularly with the West Indies. From the summit of this hill the prospect of the scenery is eminently delightful." (Vol.1, P.224)

After 1820 sea trade in Upper Houses declined, and small scale manufacturing and brownstone quarrying (begun in 1852) achieved economic importance. Some shipbuilding continued; in the 1820s the Connecticut River Steamboat Company was organized by three distinguished residents of Upper Houses, including William C. Redfield (1789-1857), scientist, naval engineer, and founder of the American Society of Science. This company financed the building in a local shipyard of the Experiment, the second steamboat registered at the Hartford custom house. In 1824, LaFayette disembarked at Upper Houses from the Oliver Ellsworth, the third passenger steamboat on the river, built by Redfield for a Hartford company in New York. Brownstone was shipped from the stone dock, and the Meriden and Cromwell Railroad had a waterside depot across River Road from the present Connecticut Hardware Supply Company, with a turntable at the foot of South Street.

In general, however, the critical and intimate connection with river and sea trade was lost after the 1820s. The natural boundaries of the river and meadows to north and south prohibited expansion in those directions. When the Hartford Turnpike began to operate in 1803-04, it was laid to the west of the old highway (Pleasant Street) on what is now Main Street. Later residential development in Upper Houses in the 19th century concentrated on the northern part of Main Street, and commercial development was centered at the northwest section of the river port village, at what is now the present center of Cromwell. During this period some residential construction continued in the river port area of Upper Houses (incorporated as Cromwell in 1851). After the Civil War the most active building period was associated with the success of quarrying operations, commercial greenhouses, and small manufacturing nearby. A significant number of structures built between 1870 and 1900 survive. Twentieth century development has been gradual, with no major intrusions into the character of the area.

The Upper Houses River Port National Register Historic District includes the streets which comprised the town center of Upper Houses until the early 19th century: School, Pleasant, South, Wall Streets and River Road. The justification for these boundaries are visual as well as historical. The area is isolated by meadows to north and south and has "its back to" Main Street on the west. The river boundary on the east includes the sites of wharves and shipyards which may be of archeological importance.

The Middletown Upper Houses Historic District is a distinctive and cohesive unit, in part because of its isolating boundaries, and in part because it was largely bypassed by later development. It is an important example of a Connecticut River town in its early phases of development. The large number of buildings dating from 1750 to 1810, on the original streets of the village center, determine the historic character of the area. These buildings include large center-chimney Colonial structures and Federal period buildings with delicate detail. Buildings of this era comprise nearly one-half of all structures in the district. There are a number of important streetscapes which retain a virtually original historic appearance. Throughout the district early buildings are dominant, and set a rhythm of scale of buildings to street and open space consistent with the appearance of the area during its period of mercantile prosperity. The structures dating from later periods in general do not detract from, and in many cases contribute to, the general feeling in the area. The most significant visual intrusion in the district is the Connecticut Valley Hardware Supply Company, a two-story commercial building on River Road. Its effect is somewhat mitigated by its placement facing the river, and by trees surrounding the building on three sides.

The Middletown Upper Houses Historic District is a rare example of the early periods of settlement and development in the Connecticut River Valley, and is of great significance in the history of the Town of Cromwell. The survival of large numbers of early buildings, the continued use and isolation of an early street pattern, the maintenance of a traditional scale, the setting with expanses of meadows, and the intimate connection with the river make the Upper Houses River Port National Register Historic District a significant representative of earlier patterns of architectural, economic and social history.


Adams, Charles Collard, Middletown Upper Houses (New York: The Grafton Press, 1908).

History of Middlesex County, Connecticut (New York: J.B. Beers Co., 1884).

"Upper Houses," Colonial Dames Series, 1925, Connecticut State Library Collections of Cromwell Historical Society and Mrs. Charles Ashley, Cromwell, Conn.

  1. Barbara Ann Cleary, Greater Middletown Preservation Trust, Middletown Upper Houses Historic District, nomination document, 1979, National Park Service, National Register of Historic Places, Washington, D.C.

Nearby Neighborhoods

Street Names
Pleasant Street • River Road • School Street • South Street • Wall Street

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