The Greek Revival house at 83 Old Boston Post Road in Old Saybrook was built in 1847 by Rufus C. Shepard, a deacon of the Congregational Church who served as County Commissioner and Representative in the state legislature.
The summer cottage at 29 Pettipaug Avenue in the Borough of Fenwick in Old Saybrook was built in 1882 by Robert N. Jackson of Middletown. The son of Ebenezer Jackson, Jr. (1796-1874) of Savannah, Georgia, and Middletown, Robert Nesmith Jackson (1845-1915) organized and served as president of the Middlesex Banking Company. The bank failed in 1913. In 1920 the cottage was acquired by Mitchell Little of Hartford and his wife, Elizabeth Hapgood, daughter of the architect Edward T. Hapgood. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 135-137.
Located at 55 North Cove Road in Old Saybrook is the Robert Bull House, built c. 1700. Also known as “the House on the Bend,” it is the oldest house in the North Cove Historic District. It was probably remodeled and enlarged around 1740, as that is when the earliest gambrel roofs began to appear. After 1851 the house was the residence of David Phelps, a successful fisherman who made a living from the eels and clams found in the neighboring harbor.
The house at 1146 Boston Post Road in Old Saybrook was built c. 1800-1803 for William Chalker. It originally stood on the opposite side of the street but was moved and an addition built when the road was straightened later on in the nineteenth century. Around that time the house was acquired by Daniel C. Spencer.
A wealthy merchant, Daniel Chapman Spencer (1823-1906) started his business career as a store clerk and then was a traveling salesman with a stock of goods carried in a peddler’s wagon. He then worked for Moulton, Plympton, Williams & Co., one of the leading wholesale dry goods firms of New York. After that company went out of business he moved on to Claflin, Mellen & Co. in New York, at the time the second largest dry goods store in the United States and soon to become the largest. He ran the company‘s notion department for thirteen years, until he broke down from the strain and decided to retire on January 1, 1868. He chose to retire to his hometown of Old Saybrook. As described in the History of Middlesex County, Connecticut with Biographical Sketches of Its Prominent Men (1884):
Mr. Spencer had previously purchased a number of acres contiguous to the old homestead property in Saybrook, known as the Chalker farm. Here he retired to spend his days. The old place was enlarged and improved and soon made to “blossom like a rose.” The meadows were turned into cranberry patches on which he spent several thousand dollars in working and improving. He surrounded his residence with trees and flowers until it now has the appearance of fairy land. Amid these surroundings he soon recovered his health and then devoted his energies to making such public improvements in the town as should tend to attract others to this beautiful spot selected by Col. Fenwick as the “garden spot of the earth,” more than two hundred years ago.
The Chalker-Spencer House was altered around 1880 when the original roof was replaced by a Mansard roof. It was later used as a boarding house.
Rev. Francis Goodwin (1839-1923) was one Hartford’s wealthiest and most important citizens. As Commissioner of Parks in the city he played the leading role in expanding Hartford’s Park system. For his father, James J. Goodwin, he designed c. 1893 a mansion on Woodland Street in Hartford. Familiarly known as the “Goodwin Castle,” the house was later torn down. Rev. Goodwin also designed c. 1880 a summer cottage for his family in the Borough of Fenwick in Old Saybrook. Rev. Goodwin led Sunday services in Fenwick in his own home until he designed and built a chapel on his property in 1883 that would be moved and enlarged in 1886 to become St. Mary’s-by-the-Sea. In 1910, Francis’ son Charles A. Bulkeley lost a bid for the governorship of Connecticut. The Goodwin family blamed the defeat on their Fenwick neighbor Morgan G. Bulkeley, who had used his influence against Goodwin. Because Bulkeley was a founder and leader of the Fenwick community, for the next thirty-five years the Goodwins rented out their cottage and vacationed elsewhere. Only after World War II did Charles Goodwin return to Fenwick. Located at 15 Pettipaug Avenue the Goodwin Cottage remained in the family until 1955, when it was purchased by Dr. Theodore Van Itallie and his wife Barbara Cox Van Itallie, who died at her Fenwick home in 2011 at the age of 91. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 115-120.
Located at 175 North Cove Road on Saybrook Point in Old Saybrook is a building erected around 1712 by John Burrows. Known as the Black Horse Tavern, it served travelers as an inn for many years and was a customs house during the brief period Saybrook was a port of entry on the Connecticut River. In the eighteenth and nineteenth centuries the area was a commercial district with a busy wharf. Ambrose Kirtland acquired the tavern in 1771 and deeded it to his son, Daniel Kirtland, in 1794. It may have been Daniel Kirtland who updated the building in the Federal style. From 1871 to 1924 the Valley Shore Railroad went right by the former tavern, which revived the tavern’s buiseness in the nineteenth century. The building was acquired by Henry Potter in 1866. He built a dock for trading vessels and a store on the site (since demolished) which he operated with his son until 1890, leaving it to his clerks, Robert Burns and Frank Young. In 1910 they moved the store, called Burns and Young, to Main Street in Old Saybrook. This marked the end of the North Cove neighborhood as a maritime commercial district. The house is now a private residence. The original Black Horse Tavern sign is now at the Connecticut Historical Society.
The sign on the Parker House at 680 Middlesex Turnpike in Old Saybrook gives it the date of 1646. The National Register of Historic Places nomination for the house gives a date of 1679. In either case, it is one of the oldest houses in Connecticut. It was built by William Parker (1645-1725). Born in Hartford, Parker settled in Saybrook. As described in Family Records: Parker-Pond-Peck (1892), by Edwin Pond Parker:
Dea. William Parker was a leading citizen, and very prominent in church and state. He is said to have represented Saybrook as Deputy to the General Court in more sessions than any other person, excepting only Robert Chapman. He was Sergeant in Train-band as early as 1672, and in 1678-9 the town voted him five acres of land for services “out of the town” in the Indian wars. He was elected Deacon before 1687, and probably continued in that office until his death. He was a lay member of the Saybrook Synod of 1705 that framed the “Saybrook Platform” for the churches of Connecticut.