Historic Buildings of Connecticut

Exploring the Nutmeg State One Building at a Time

Underground Railroad

Whitehall Mansion (1771)

The earliest structure built on the original site of Whitehall Mansion, located in the section of Mystic which is in the town of Stonington, was constructed around 1680 by Lt. William Gallup. A tavern and stagecoach stop stood on the site in the 1750s. Whitehall Mansion, named after an ancestor’s home, Whight House, in Essex, England, was built in 1771-1775 by Dr. Dudley Woodbridge (who, in his youth, had made an interesting sketch of buildings in Deerfield, Massachusetts). A secret room in the attic may have housed runaway slaves. Dr, Woodbridge died in 1790 and the house was later owned by the Rodman and Wheeler families. The Mansion‘s last resident, Florence Grace Keach, donated the house to the Stonington Historical Society in 1962 in order to save it from demolition when Interstate-95 was being constructed. The house was moved approximately one hundred yards north and restored. For a time, it was open for tours, but was purchased by the Waterford Hotel Group in 1996 and is now the Whitehall Mansion Inn.

The Mather-Douglas House (1811)

The Mather-Douglas House was built around 1811-1813, on South Main Street, off South Green in Middletown. It is a Federal style house with later Italianate additions. Built by a Mather, a later owner of the house was Benjamin Douglas, who was a factory-owner and politician. He was a founder of the W. & B. Douglas foundry company (Wesleyan’s Douglas Cannon was named after him) and he was a member of the state general assembly and mayor of Middletown from 1849 to 1855. He was an abolitionist and there is “strong circumstantial evidence” that his house was a stop on the Underground Railroad.

George Greenman House (1839)

George Greenman was the eldest of three brothers who founded the shipyard in Mystic known as George Greenman & Co. His house on Greenmanville Avenue was built in 1839 and was enlarged and further ornamented later in the nineteenth century. Greenman’s brothers initially resided in the house with him, until they built their own homes nearby on Greenmanville Avenue. The Greenman home is reported to have been a stop on the Underground Railroad. The Mystic Seaport living history museum acquired the house from George Greenman‘s great-granddaughter in 1970. The house has a Historic Structures Report.

Thomas Hart Hooker House (1770)

The Thomas Hart Hooker House, on Main Street in Farmington, was built in 1770 by Judah Woodruff for Hooker, a descendant of Thomas Hooker and of Stephen Hart, one of the founders of Farmington. Hooker had married Sarah Whitman Hooker in 1769 and in 1773 they moved to what is now West Hartford. The house was later owned by Samuel Deming, an abolitionist who used his home as a stop on the Underground Railroad. Deming also joined with Austin Williams and John Treadwell Norton in bringing the Africans from the Amistad to Farmington in 1841. The house, now owned by Miss Porter’s School, is on the Connecticut Freedom Trail.

Francis Gillette House (1834)

Francis Gillette was a politician, lecturer and abolitionist. He pursued agriculture in Bloomfield and lived in an unusual 1834 Greek Revival style stone house on Bloomfield Avenue. In 1852, Gillette moved to Hartford, founding the Nook Farm neighborhood with his brother-in-law, John Hooker. Francis Gillette served as a senator and was the father of actor William Gillette. The house, which was used as an overnight stop for fugitive slaves on the Underground Railroad during the Civil War, was moved to a new location on Bloomfield Avenue in 1990, after being vacant for 17 years.

Elijah Lewis House (1790)

The Elijah Lewis House was built around 1780 or 1790 by Farmington‘s master builder, Judah Woodruff. Lewis was a farmer and served as a quartermaster in the Revolutionary War. Both he and his son, Elijah Lewis, Jr., were abolitionists and the house was a station on the Underground Railroad (it is on the Connecticut Freedom Trail). In 1977, to improve the flow of traffic on Farmington Avenue, the house was moved back from the road and rotated 90 degrees, with a new address on Mountain Spring Road. The house, which is currently for sale, was also occupied by the artist, Robert B. Brandegee, who left paintings on some of the interior door panels.

John Pierpont House (1767)

The John Pierpont House, on Elm Street in New Haven, was built in 1767 and is located between the Jonathan Mix and Ralph Ingersoll Houses. The house was used by British soldiers as a headquarters and hospital during the Revolutionary War, when they raided New Haven in 1779. It remained in the Pierpont family until 1900, when it was purchased by Rev. Anson Phelps Stokes, Secretary of Yale University, who added two symmetrical rear wings. The house was acquired by Yale in 1921 and “restored” by architect J. Frederick Kelly in 1929. Other alterations have been made over the years, some being removed by Kelly, who sought to recreate a Colonial appearance. Yale has used the house as the Faculty Club, Office of Undergraduate Admissions, and most recently as the University’s Visitor Center. The building’s interior and exterior have been extensively renovated since it became the Visitor Center in 1995.