Windham County

Killingly Town Hall // 1876

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The economic center of the town of Killingly, Connecticut is the village of Danielson, which is located at the confluence of the Quinebaug and Five Mile rivers. The area developed as an industrial village and prospered as the town’s center through the late 19th and early 20th centuries. The present-day town hall building was originally constructed in 1876, not as a civic building, but as a multi-purpose music hall and G.A.R. Hall. The Victorian/Ruskinian Gothic style building was constructed of brick with stone trim. The building was later acquired by the town in 1906 and has served as the town offices ever since. Besides the unfortunate replacement windows, the building is well-preserved by the town.

Harris Sayles House // c.1860

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This handsome Italianate style house is located on Dog Hill Road in Killingly Center, Connecticut. The house appears to date to the years just before the Civil War and historic maps show that the property was owned by Harris Sayles, a co-owner of the large woolen mill in nearby Dayville. The home was built for Harris and his wife, Phebe. The house stands out for its two-tiered gallery of porches with large chamfered posts and paired brackets and has some Classical corner pilasters and door surrounds noting the transitional period from Classical Greek Revival style to the romantic Italianate style.

Harris and Sabin Sayles Mansion // c.1845

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Located in the Dayville section of Killingly, Connecticut, you can find a row of large mansions built for mill owners and managers from the 19th century. This house dates to the 1840s and by the 1860s, was owned by Harris Sayles (1817-1893) and his brother, Sabin L. Sayles (1827-1891) who together, co-owned and operated a large woolen mill in the town (featured previously). It is not clear if the Sayles brothers lived in the home, but they likely rented it to higher-level employees at the mill as they both had other homes in town. The two-and-a-half story mansion is a great example of the Greek Revival style in the town, with the side gable roof extending over the full-height portico with doric columns. The mansion was built across the street from the village church, also in the same style, but that building was demolished by 2011.

Sayles Mill // 1882-2023

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Dayville, a mill village in the town of Killingly, Connecticut, is typical of many similar 19th century villages in the region. Dayville was named after John Day (1756-1838) a Revolutionary War veteran who later owned the water privileges on the Five Mile River. With the opening of the Norwich and Worcester Railroad in 1830, Dayville became a stop along the route and also became a hub for freight transport for other manufacturing villages along the river. In 1858, brothers Harris (1817-1893) and Sabin Lorenzo Sayles (1827-1891) from Rhode Island, purchased a mill site in Dayville and established a woolen manufacturing company. Harris retired in 1879 and Sabin continued the business as the Sabin L. Sayles Company. Sabin had a modern brick mill building constructed here in 1882-1883 which employed 250 people in production of woolen broadcloth. After Sabin’s death, the company was sold and modified numerous times, eventually becoming a metal products plant and later was left vacant. In the 2010s, funding and plans were begun to redevelop the old mill, but that was abandoned after a massive fire in 2023 destroyed the building, leaving just the six-story tower intact.

Photo courtesy of Journeysthrumylens

Darius Knight House // c.1830

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Another of the stunning early 19th century homes in the charming town of Chaplin, Connecticut is this transitional Federal/Greek Revival home built around 1830. The house appears to have been built for Darius Knight (1792-1882), a Deacon at the nearby Congregational Church. Of an interesting note, the Knight House is located across the street from the E. W. Day House, thus the intersection was colloquially known as the Knight and Day Corner. The house’s gable-end form with gable reading like a pediment supported by corner pilasters are all clearly Greek Revival style, but the fan lights in said gable and as a transom window are holdouts of the tried-and-true Federal style which dominated up until that point. What a great house!

Old Chaplin Public Library // 1911

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In his will, lifelong Chaplin, Connecticut resident William Ross (1833-1908) bequeathed his hometown funds to erect its first purpose-built public library. As planning began, his widow, Emily Jones Ross donated even more to fund a building fitting of her late husband. The Queen Anne/Romanesque Revival style library is built of pressed brick with granite trim and features a prominent rounded corner bay of cedar shingles. The masonry work was done by George E. Snow but I could not locate the architect. The town outgrew the library and moved it into a new building nearby, selling the William Ross Public Library to a private owner, who appears to be renovating it now.

Chaplin Congregational Church // c.1815

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Years before the small town of Chaplin, Connecticut was incorporated as a town, early residents here had this Congregational church built at the future town’s center. The following decades would see the village develop into a cohesive street of Federal and Greek Revival style dwellings and shops, many of which remain to this day. The church was technically completed by 1815, but it would be decades until funding was acquired to add the steeple, pews, and other finishings for the edifice. The structure sits on a raised stone foundation and is prominently sited on the town’s main street.

Orin Witter House // 1821

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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.

Lincoln-Chrysler House // c.1830

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This charming brick Federal house sits on the main street in the quaint village of Chaplin, Connecticut. Due to its style, the house likely dates to 1830 as a late-Federal home as the village was seeing development. The original owner is not known, but the property was later occupied by Mason Lincoln in the mid-late 19th century. By the early 20th century, the property was owned by members of the Chrysler family, first by Mintin Asbury Chrysler (1871-1963), a botanist, mycologists and paleobotanist. The house was later inherited by Mintin’s son, Sidney Chrysler, who was a known puppeteer who converted some spaces in the property for puppet shows until his death in 1999.

Gurley Tavern // 1822

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Chaplin, Connecticut was incorporated in 1822 and in that same year, this stately Federal style residence was built and operated as a tavern by Chauncey and Julia Gurley. The house in the late 19th century was used as a private school and residence and was later owned by Ruth E. Snow Bowden (1895-1983) known lovingly as “The Quilt Lady”. Ruth was one of the foremost quilt-makers in Connecticut and her Chaplin home, as a result, became known as The Quilt Shop. By the late 1900s, the tavern was converted to an inn, but closed years later from few bookings. The new owners have restored and maintained this charming old tavern back to its original appearance.