Orin Witter House // 1821

The Witter House of Chaplin, Connecticut was built in 1821 and owned by three generations of medical doctors all named Orin Witter. The Witter House stands on Chaplin Street and is among the finest Federal style residences in this part of the state. Orin Witter had the house built just before the town was incorporated in 1822 and would also serve as the town’s first Clerk. The Witter House is five bays wide, with paired chimneys at the ends of the hip roof. The centered entrance is flanked by arched sidelight windows and has a fanlight above. The fanlight detail is echoed by semi-elliptical fan louvers above each window. The roof has a monitor section at its center. Due to its architectural merit and state of preservation, the house was individually listed in the National Register of Historic Places.

Benjamin Bosworth House // 1800

One of the most unique houses in Connecticut is this massive Federal style residence located in the small town of Eastford. Built next to the Congregational Church of Eastford (1829-2023), which burned down in 2023 by arson, the massive house has been known as both the Benjamin Bosworth House and Squire Bosworth’s Castle due to its first owner, Benjamin Bosworth (1762-1850). According to the Bosworth Family, the house was built in 1800 by Bosworth was a wealthy merchant, who hired Vini Goodell, a local carpenter to design and build the large Federal home. The house was completed by 1801 when the local Masonic group met in the building. As Bosworth was also a merchant, he used the basement as a storeroom. The house is also unusual for its monitor roof, a rarity in Federal period construction, which reads like a second structure on the house, due to the building’s size. After Bosworth’s death, the house was occupied by his niece, and was later purchased by Elisha Grant Trowbridge in 1897. Trowbridge was a grand-nephew of General Nathaniel Lyon (1818-1861), a local hero who was the first Union general killed during the Civil War. Trowbridge, an engineer, lived here until he died in 1963 at the age of 96. Later owners have had the monumental task of restoring and maintaining this behemoth of a house, to great success.

Lewis June House // 1865

The Lewis June House sits on North Salem Road in northern Ridgefield, Connecticut, and is one of the finest Second Empire style homes in this part of the state. The c.1865 home was built for Lewis June (1824-1888), who was in the circus business, and it replaced an earlier home on the site that burned. Lewis June was a partner in the June, Titus and Angevine & Co. Circus that as early as 1842 toured 85 towns in six states. The circus wintered in Ridgefield. Past owners have since found many horseshoes, largely of small horses, on the property, suggesting that June kept the circus’ horses and ponies on this property. The home has been preserved thoughtfully and was listed on the National Register of Historic Places in 1984.

Dr. Aretus Rising House // 1854

Dr. Aretus Rising was born in Suffield, CT in 1801, part of one of the oldest families in town who settled here. His father was a farmer of modest means who could not afford the ability to let his eight children attend school routinely as he needed help on the family farm. He eventually moved to Western MA where he graduated the Berkshire Medical School in 1826, soon after opening a practice in Florida, NY before moving back to Massachusetts. He operated a doctors office in Suffield starting in 1845, running it until 1871, stopping due to poor health and failing sight. He lived most of his later years in this modest Italianate home. The house features broad overhanging eaves and a porch supported by stunning lattice columns.

Lewis-Zukowski Farm // 1781

On the rural back roads of Suffield, CT, it is amazing how many historic farmhouses you can stumble upon. This is the Lewis-Zukowski Farmhouse, built in 1781, as one of the earliest brick homes built in this part of the state. When Hezekiah Lewis (?-1805) built his house in 1781, he was a farmer of modest prosperity. By the time of his death in 1805, he was somewhat wealthier, perhaps because of his second marriage in 1794 to widow Ruth Phelps, as his 91-acre farm. His estate indicates he was a traditional farmer of the period: he had a yoke of oxen, 2 horses, 2 cows, and 2 pigs, suggesting that he was primarily raising sustenance for his family, not products for market. Michael Zukowski arrived in Suffield in 1888 with his family as an immigrant from Poland. Zukowski worked on a farm in town for $8.00 a month plus board for local tobacco farmer Calvin Spencer. He had saved enough by 1905 to pay Hiram Knox (then the owner of the former Lewis Farm) $2,800 in cash, purchasing the property. Zukowski worked the farm until the 1920s, when his son took it over and he moved to another farm nearby. The house remained in the family one more generation until it was sold out of the family. It remains as an architecturally and culturally significant farm in Suffield.