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Indian Hill Avenue Historic District

Portland Town, Middlesex County, CT

The Indian Hill Avenue Historic District was listed on the National Register of Historic Places in 1983. Portions of the content on this web page were adapted from a copy of the original nomination document. []


Indian Hill Avenue is a short street running west from Main Street to the Connecticut River in the northern part of Portland, Connecticut. The Connecticut River bends westward at this point and then turns southward again, so that the river forms the western and northern edges of the neighborhood. Just to the north is a large island in the river, Gildersleeve Island. The land is high enough above the water as to be generally free of swampiness, though there is some marshy ground around the point where a small brook, Taylor Creek, flows into the river. The land slopes upward forming a plateau near the middle of the avenue, which takes a slight bend at this point, then it falls off, rising again as the avenue joins Main Street. The soil in the neighborhood has been classified into three types of sandy loam.

Of the 32 major structures in the Indian Hill Avenue Historic District, 15 have been judged to be noncontributing to the historical character of the district, a character created by the remaining 17 buildings, most of which are 18th or early 19th century houses. Four of the noncontributing buildings form the complex of the Petzold Marina, a pleasure-craft sale, storage and repair business built on the site of a much earlier shipyard: presumably the concrete and steel structures which make up the marina have covered over any historic archaeological remains of earlier enterprises. Two others of the noncontributing structures are the brick and cinderblock buildings of the rubber factory. In addition to these, there are six houses of fairly recent construction, an old house which has lost its historic appearance (663 Main Street), the recreation pavilion at the end of the avenue, and a cinderblock bowling alley set back from both Main Street and Indian Hill Avenue.

Of the historic structures in the Indian Hill Avenue Historic District, eight are from the 18th century, including both 1-1/2- and 2-1/2-story examples and a gambrel roof as well as the standard gable. These all have their ridgelines set parallel to the road and generally have central chimneys, symmetric three or five-bay facades with central entranceways, brownstone underpinnings, and at least some raised panelling in most of the interiors. Three of the contributing buildings are Greek Revival houses with their gable ends facing the road and a pediment effect created by a full cornice return. The Indian Hill Avenue Historic District also includes three rather plain Victorian-period houses, with Carpenter Gothic, Stick style and Eastlake trim around their entranceways. In addition to the houses, there are two stores which date to the 1850s, one built of brick, and a long, narrow four-family tenement built in 1873 to house workers at a steam sawmill once located on the site of the rubber factory. The Indian Hill Avenue Historic District's houses are generally quite plain, with limited ornament confined to the entrances. Most are in an unrestored state, with more recent additions such as dormers and porches and modern siding materials partly obscuring their historical integrity.

The Indian Hill Avenue Historic District includes one significant object, in addition to the inventoried structures: a wrecked wooden barge, probably built at the Gildersleeve shipyard around 1900, and lying partly buried in the riverbank at the northwest corner of the marine's lot.

Several sites within the Indian Hill Avenue Historic District have been associated with reports of Indian burial discoveries. No formal archaeological testing has occurred, but the reports of burials, osteological materials purported to have come from these burial sites, and a wealth of cultural material remains, such as projectile points, recovered from the area of Indian Hill Avenue all suggest that the area possesses prehistoric archaeological significance. Objects in collections from Indian Hill include many prehistoric archaeological artifacts; numerous projectile points some early Archaic period bifurcate points, and undateable objects such as stone mortars and tool pre-forms.

The boundaries of the Indian Hill Avenue Historic District were chosen to reflect the patterns of historic settlement, insofar as they are known. The river forms easily delineated borders on the north and west, and Main Street was taken as the eastern boundary because its character is predominantly 19th century, reflecting a later period of growth in the area's history than the largely 18th century Indian Hill settlement. The boundaries of the Indian Hill Avenue Historic District include all of the hypothetical extent of burials as posited by the report of the Public Archaeology Survey Team, as well as coinciding closely with the boundaries of the Wangunk tract sold in 1765.


Indian Hill Avenue has been the site of human activity for thousands of years, and the evidence of this habitation makes the area a significant addition to the National Register of Historic Places. From the relatively recent past, the barge wreck, tenement house, and two mid-19th century stores recall the importance of the area as a commercial center and shipbuilding site. The houses along Indian Hill Avenue are historically significant, as they were inhabited by some of the earliest English settlers of the area, and later by some of the ship carpenters which made the area a prosperous place. The historical development of the neighborhood is mirrored in these structures. Although they are plain and somewhat modernized, these houses illustrate well the vernacular architecture of the 18th and 19th centuries, and therefore the Indian Hill Avenue Historic District has an architectural significance as well. Finally, Indian Hill Avenue has a long-standing reputation as one of the prime locations for the discovery of Indian artifacts in the entire Middletown area. Although no formal archeological testing has been done to date, the concentration of artifacts in the area and the documentary and physical evidence of several burials there give Indian Hill Avenue an archaeological potential.

At the time of the English arrival, the town which is now Portland was occupied by people called Wangunks or Wongunks. Although they had their own leaders, they were apparently a subsidiary group of the Mattabesetts of Middletown, and through them, were part of a larger political entity embracing many of the groups in the greater Hartford-Middletown area. Beginning in 1672 the town of Middletown began purchasing land on the east side of the river from the Wangunks, who reserved from the sale 100 acres in the Wangunk meadows north of the district, 23 acres around what is now Indian Hill Avenue, and about 200 acres near the junction of Main and Bartlett Streets. In 1748 part of the last-named tract was sold for the second parish meeting house, and in 1765 the remaining Wangunk land was sold and divided into parcels. The proceeds were used to support the remaining Wangunk people in the town, but there were only a few left: in 1764 the majority of the group joined the Podunks and others at Farmington, and later migrated to Stockbridge, Massachusetts, then New York, and finally settled in 1834 in Calumet County, Wisconsin. As late as 1850, however, Wangunk visitors were reported in the area, having returned to Portland to visit the graves of their forbears ("Indian Proprietors of Mattabeseck"). In addition to the migrants, it appears that there were some Wangunks who stayed in the area but adopted more of the Europeans' customs, such as Christianity and individual ownership of land.

Throughout 19th-century writings on Portland (Field, 1819,1853; Beers, 1884) Indian Hill is described as an important Wangunk burial place, and this undoubtedly explains why the Wangunks reserved that place after selling off most of their other land. According to this tradition, the Wangunks used the place for burial before the English arrival and for some time thereafter. Although the descriptions in the local histories are sketchy, the reported burials are intriguing because they show the indigenous culture changing in the face of European settlement. Supposedly, the "sitting" posture was common, with ornaments, weapons, utensils, and "wampum" placed in the grave. Some of these items appear to have been European manufactured goods, such as a small brass cup found in a child's grave.[1] Field (1819) described the place as having some inscribed monuments after the English fashion, and one of these was recorded in 1853: "Here lies the body of John Onckous, who died Aug., the 30, 1722, aged 26 years." Although the digging of foundations, road work, and erosion have ruined many of these discoveries, it is not unreasonable to assume that burials from this early historic period remain, and if carefully, respectfully investigated by archaeologists, could illuminate the history of Portland's native inhabitants.

Indian Hill Avenue's archaeological potential is also suggested by the wealth of "arrowheads" and other artifacts collected there over the years. In the late 19th century, amateur archaeologist Charles H. Neff collected many things there, and proclaimed it one of the best spots in the area for digging up points and similar relics. His collection is fairly well cataloged as to time and place of discovery (mostly surface collection after plowing) but is presently stored at Wesleyan University and is not available. Other collections have been less specific, but the plethora of projectile points in these local collections suggests that Indian Hill Avenue was the focus of unusually intense activity. Moreover, there are a great number of Archaic-period bifurcate points which indicate activity at this spot for several thousands of years. Although systematic evaluation of the district's archaeological potential is lacking, the weight of documentary evidence and the numerous artifacts discovered by collectors suggest that the area is far above the ordinary in the duration and intensity of pre-European activity, and should be treated with a careful regard for potential archaeological resources.

Specifically, the human skeletal remains uncovered in the proposed Indian Hill Avenue National Register District are a significant archaeological resource for the study of the Aboriginal/European contact period and the interaction of Indians and Whites during the 17th and 18th centuries in central Connecticut. Human osteological remains and the information to be derived from study of their morphology, context and artifactual associations, provide a rare body of data for the reconstruction of late prehistoric and early contact period demographics, stature and disease, as well as specific attributes of aboriginal society and ideology.

The recovered skeletal remains along Indian Hill Avenue, their proximity to one another and their artifactual and documentary associations clearly indicate that this is the site of an aboriginal cemetery of the historic period. The burial sites have yielded evidence of European items found in other similar sites in association with aboriginal burials of the contact period. Specific comparative information which may be used to place the site within an interpretive context is provided by the historic Indian burials excavated at the West Ferry site on Conanicut Island in Rhode Island.

Fifty nine Narragansett graves dating to the 17th century were excavated by William Simmons. The associated artifacts of the same type as the brass cup and trade beads recovered at Indian Hill permitted dating of the site to the 17th century. At Indian Hill the excavated graves are supplemented by other graves with stone markers with inscribed Indian names of the 18th century. In addition, the flexed burial position at Indian Hill (usually erroneously reported as a sitting position in the historical records), was the dominant position for mortuary ceremonialism and body orientation in southern New England during the historic period. The historic skeletons at the West Ferry site were flexed and oriented towards the southwest.

The unexcavated portion of the Indian Hill cemetery is undoubtedly quite large, since 59 graves were uncovered together in Rhode Island and less than a dozen at Indian Hill. The archaeological potential of this site is great in that it probably contains intact deposits of historic Indian burials. Large areas comprising the backyards along the south side of Indian Hill Avenue remain unexcavated suggesting that the integrity of this site has remained largely unaltered by the 18th century architecture comprising the Indian Hill Avenue Historic District.

To date, relatively few examples of contact period Indian cemeteries have survived the ravages of time and development in Connecticut and particularly in Portland. Thus, in terms of local survivals the Indian Hill cemetery is probably unique. The site undoubtedly contains trade goods, aboriginal products and the skeletons themselves, which are invaluable and rare sources of information for understanding such problems as the form and physical condition of contact period Indian populations, the nature of disease and health practices among these people, the attributes of religious ideology, ceremonial forms and mortuary practices, and the prevalence of aboriginal technology and the adoption of goods of European origin. The information contained within the Indian Hill site would provide comparative materials so that research questions designed to distinguish Connecticut aboriginal peoples from those better known to the north, east and west, could be answered.

The architectural significance of the Indian Hill Avenue Historic District is much more concrete. No where else in Portland is there such a concentration of 18th-century and early 19th-century houses. Although not as well-preserved as those in some other districts in the state, these houses are important locally because they illustrate the typical building customs of the area's early settlers. The use of native stone (Portland brownstone), the central stacks, the orientation of the early houses with their ridge parallel to the street, raised-panelling interior walls, and the symmetrical three- and five-bay facades are the hallmarks of vernacular 18th century building. The houses are devoid of ornament, except for two which have Federal-period entranceways. The nineteenth century is well-represented by the typical Greek Revival house at 57 Indian Hill Avenue, whose corner pilasters and fully returned cornice are representative of country building of the period. Victorian decorative devices may be seen in the bargeboard-like entrance trim at 40 Indian Hill Avenue, the Stick-style bracing next door, and the Eastlake turnings applied to the window trim of 660 Main Street. These later buildings illustrate how vernacular building, while still rather plain, incorporated decorative elements from the more fully developed historical styles of the 19th century.

The buildings are also important for local history, because they are associated with the historical development of Indian Hill Avenue (earlier called Shipyard Lane) as a shipbuilding and commercial center. The English had built a few small vessels there even before the Wangunks sold the land, but the shipbuilding potential of the place was one of the reasons local settlers petitioned the Assembly to buy the land at Indian Hill. The river was deep there, and sheltered from storms in nearly every direction, since the river took a bend there and had Gildersleeve Island to the north. Houses of early settlers include the Job Bates House (3 Indian Hill Avenue), built by a blacksmith "through mistake"[2] on Wangunk Land before its sale in 1765. Another blacksmith, Thomas Stevenson, and his ship carpenter brother Robert, build the gambrel-roofed house at the end of the street soon after 1765; it was later owned by the operator of the ferry which crossed the river between Middletown and a landing at the end of the lane. Within a few years there were four or five small shipyards building vessels of all sorts, and consequently blacksmith shops, hardware and supply stores, taverns (such as 5 Indian Hill Avenue) and small craft shops connected with the shipbuilding industry. The Philip Gildersleeve House, 58 Indian Hill Avenue, is especially important, since he was the progenitor of a shipbuilding family that would dominate the economy of the place throughout the 19th century and who gave the name Gildersleeve to the locale. Philip was master carpenter for the building of the 514-ton U.S. ship Connecticut in 1798. Other houses with significant historical associations are the house of shipyard owner George Lewis, Jr. (46 Indian Hill Avenue) and those of master carpenters Elijah Shepard, John Button, Richard Conklin and William Dixon (32, 15, 57 and 52 Indian Hill Avenue). After about 1840, when there were numerous yards and 90 ship carpenters in Portland (then called Chatham), shipbuilding declined, but even in 1860 when there was but one yard left, S. Gildersleeve and Sons, the industry was second only to the famous Portland brownstone quarries in the number hands employed. After the Civil War, the Gildersleeves turned to building barges, scows and lighters, as railroads and iron ships took away their earlier business of large wooden ships. The barge wrecked on the banks of the river is a typical product of the Gildersleeve yard in its last phase, the only visible relic of this important industry whose site is now occupied by the newer marina.

The Gildersleeve family did not confine itself to shipbuilding. In the 1850's Sylvester Gildersleeve built the brick store on the corner for one of his sons, and in later years the Gildersleeve country store became more financially important to the family than the yard. Sylvester dreamed of a manufacturing village at Indian Hill, and beginning in 1868 built a steam-powered sawmill and lumber yard near his shipyard. He also constructed a four-family tenement to house the workers, and in addition bought up and rented out many of the previously-built houses in the area. Although the site did not become the boom town he hoped for, the sawmill and lumber yard were important enterprises in their own right, as well as contributing material for the shipyard. One of their specialties was Southern yellow pine, first imported for shipbuilding, but later in great demand in the Victorian period for interior trim. The store, barge wreck, tenement house, and Philip Gildersleeve homestead remain today to mark the enterprise of this important Portland family, one which gave its name to the vicinity as well as endowing local churches and schools.


  1. Brass would undoubtedly be European in origin, although copper objects may have come from the Great Lakes region.
  2. Connecticut Archives, Series I, Indians, Vol. II. State Library, Hartford.


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

Commemorative Biography of Middlesex County. Chicago: J.H. Beers, 1905.

Connecticut Archives, Series I. Indians, Vol. II. Connecticut State Library.

Field, David D. A Statistical Account of the County of Middlesex. Middletown: Clark & Lyman, 1819.

Field, David D. Centennial Address, Middletown and Its_ Parishes. Middletown, 1853.

Gildersleeve Papers, RG 69:95, State Library, Hartford.

Gildersleeve, Sylvester. "Gildersleeve Family for 100 Years," MS, State Library.

Gildersleeve, Willard H. Gildersleeves of Gildersleeve, Connecticut. Merident: Journal Publishing Co., 1914.

"Indian Proprietors of Mattebeseck," Addresses Delivered, at the Dedication of Indian Hill Cemetery. Middletown: C.H. Pelton, 1850.

McAuliffe, Margaret. Seventy-Fifth.Anniversary of Portland, Connecticut. Portland: Portland Board of Trade, 1916.

Neff, Charles H. "List of Indian Localities about Portland, Connecticut, and Neighboring Towns and a Catalogue of Indian Relics Found in this Vicinity," State Library, Hartford, 1927.

Portland Historical Society. History of Portland, Connecticut. Portland, 1976.

Simmons W. Cautantowwit's House: An Indian Burial Ground on the Island of Conanicut Narragansett Bay. Brown University Press, Providence.

Van Beynum, William J. (comp.J. Portland, Connecticut: 125 Years of Incorporation. Portland: Selectmen's 125th Anniversary Committee, 1966.


Welles, William. Map of Wangunk Land. MS, 1956. Connecticut Archives, Series I, Indians, Vol. II, p.140. State Library, Hartford.

Walling, H.T. Map of Middlesex County, Connecticut. New York: H. & C.T. Smith & Co., 1859.

Beers, F.W. County Atlas of Middlesex, Connecticut New York, 1874.

Sanborn Map Company. "Portland, Middlesex County, Connecticut," Plate 2, 1907. Portland Town Hall.

Bruce Clouette, consultant, and John Herzan, Connecticut Historical Commission, Indian Hill Avenue Historic District, nomination document, 1980, National Park Service, National Register of Historic Places, Washington, D.C.

Street Names
Indian Hill Avenue • Main Street

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