Historic Buildings of Connecticut - Exploring the Nutmeg State One Building at a Time

Wakeman B. Meeker House (1855)

In 1832, Wakeman B. Meeker, Sr., a prosperous shipping merchant, acquired the old Bulkley residence at 824 Harbor Road in Southport. He formed the firm of Meeker & Sherwood with his partner, Simon Sherwood, in the 1830s and built a wharf and three warehouses across from his residence. They owned three schooners and seven sloops engaged in freight and passenger service. The firm later became W.B. Meeker & Son. Next to the Bulkley residence, Meeker erected a new house, 25 Westway Road, for his son c. 1850-1855. The front porch, decorated with highly ornamental sawed scrollwork, was added in 1891. After Meeker’s death in 1862, his son, Wakeman B. Meeker, Jr., carried on the business until his death in 1915.

Benjamin and George Doolittle House (1824)

At 366 Main Street South and Doolittle Hill Road in Woodbury is a house built c. 1823-1824 by brothers Benjamin and George Doolittle. The brothers divided the house equally between them, including the basement (the house is on a hill and there is an entrance to it on the left side of the house, not visible in the image above), where Benjamin and George each had a Dutch oven. During the War of 1812, Benjamin Doolittle (1798-1868) was a drummer boy with the New Haven Grays. He became a cabinetmaker, manufacturing chairs in Litchfield, and moved to Woodbury in 1822. He was an active member of King Solomon’s Lodge, No. 7, of Free and Accepted Masons and of St. Paul’s Episcopal Church. From 1854 he ran an express business between Woodbury and New Haven, as well as routes to other points, such as Waterbury. He died en route to New Haven in 1868. The house remained in the Doolittle family until George’s widow, Betsey Collier Moore Doolittle, died in the Blizzard of 1888.

Charles Chauncey Hall House (1750)

The Charles Chauncey Hall House is located at 551 Maple Avenue in Cheshire. The house’s history is described in Edwin R. Brown’s Old Historic Homes of Cheshire (1895):

This house was built by [Col.] Benjamin Hall for his son, Charles Chauncey Hall, about the year 1750, and is one of the best examples of the old, lean-to houses, with stone chimney, now standing. Charles Chauncey Hall married Lydia Holt in 1751, and a large family were born and brought up here, among whom was Charles C, the grandfather of Charles H. and Frank N. Hall, also Benjamin Holt Hall, who also resided here during his life. Two daughters of the latter married Joseph Hitchcock, the father of Samuel. Another daughter married Capt Asa Peck, and another married George Peck, who lived here. Charles C. Hall, while a resident, held a negro boy as a slave. The boy ran away, and Mr. Hall advertised his escape, offering a reward of $2 for his capture. Charles Chauncey Hall died in 1776.

It is related of George Peck, a later resident, that in the days of the militia he was duly appointed corporal of the Cheshire company. Stepping up to the top-most step of the Congregational Church, he remarked: “I thank you for the honor conferred upon me by appointing me your corporal. I feel abundantly qualified for the position, but I shall not accept.” This speech was in keeping with Mr. Peck’s ready wit.

This property has been in the hands of Col. Benjamin Hall and his direct descendants for 170 years. If this old house had the power of speech, what a life history it would be able to disclose!

Dr. Jeremiah West House (1760)

In 1805 Dr. Jeremiah West (1753-1806), who had served as a surgeon in the Revolutionary War, deeded the house at 4 Tolland Green in Tolland to the Missionary Society of Connecticut. The house, built circa 1760, served for a time as Tolland’s Congregational Church parsonage. John H. P. Rounds acquired the house from the church in 1898. Rounds was the last driver of the horse-drawn mail stage from Rockville. He also served as Assessor in Tolland and was a candidate for Connecticut state house of representatives from Tolland in 1904.

David Bassett House (1790)

The house at 20 State Street in the Pines Bridge Historic District in North Haven was built c. 1790. Around the 1830s the house was willed to David Bassett by his grandfather. The current front entry porch was added in 1936 when the house was remodeled.

Congregational Church of Eastford (1829)

UPDATE: The 1829 Church building was destroyed by a fire on April 22, 2023.

The Congregational Church in Eastford was organized September 23, 1778. A meeting house was soon erected on Lieutenant John Russel’s land. The present church, located at 8 Church Road, was dedicated on December 23, 1829. The old church was removed, as described in Richard M. Bayles’ History of Windham County, Connecticut (1889):

Esquire Bosworth purchased the old meeting house, removed it from the common and made it into a dwelling house. The day for the removal was fixed, men were invited with their teams, and all was ready for the start, when a delegation came to Esquire Bosworth, saying the oxen would not draw unless the teamsters were treated. Esquire Bosworth had recently identified himself with the temperance cause, and the “rummies” hoped to bring him to terms, but they mistook their man. The words of his pastor at his funeral, “He was one of the firmest oaks that ever grew upon Mt. Zion,” were well spoken. Instantly the reply came, “It will rot down where it is, first.” Enough teams were unhitched to prevent the moving that day, but immediately an offer came from neighboring towns to furnish teams that would draw though the teamsters were not treated. Esquire Bosworth left a legacy of a thousand dollars, the interest to be applied to help support a settled orthodox minister, and for the support of no other.

Today the Congregational Church of Eastford is a nondenominational church.

Isaac Stewart House (1885)

The house at 65 Woodland Street in Bristol was built by house builder Isaac Stewart. It was the home of Frank Curtis, who worked at New Departure Manufaturing Company.