White Oak Schoolhouse // 1840

When the first white settlers of present-day Southbury, Connecticut, traveled up the Housatonic on rafts in 1673, they spent their first night under a white oak tree in what is now Settlers Park. That section of Southbury became known as White Oak for this early history. As this part of town developed and the population grew, another schoolhouse was needed. In around 1840, this Greek Revival style school building was constructed and has stood proudly on Main Street in the nearly 200 years since. The school now shares the same lot as the Reverend Graham House and has most recently been occupied as an antiques store.

United Church of Christ Southbury // 1844

Originally, the parishioners living in present-day Southbury would travel to Woodbury Center to attend church services. This changed after the Southbury parish was incorporated in 1731, voting to erect a church a year later. Founded in 1732, the Southbury Congregational Church was dwelled in several sites until the third church was built on the present site in 1844. This Greek Revival style church features Doric pilasters and Ionic columns at the recessed portico with a large pediment above with ornate scroll carvings around the clock. The church remains well-preserved and a visual landmark on the Main street.

Curtiss-Fabrique House // 1810

Located on Main Street in Southbury, this stately Federal style mansion stands out as one of the most unique and interesting in town! The house here was originally built in the 1760s as a more modest Georgian house by members of the Curtiss Family, one of the earliest families to settle in the area after land here was purchased from the Potatuck Native Americans. In the early 19th century, the house was modernized in the fashionable Federal style, giving the house the present appearance. The facade is dominated by an excellent doorway with a projecting Palladian portico above. The property was later owned by Benjamin Fabrique.

Dublin Hill Deck House // 1974

I don’t share Mid-Century buildings on here enough, mostly due to the fact that so many of the houses of the period are secluded down winding driveways and surrounded by trees! This stunning house is located in Southbury, Connecticut, and is a great example of a Deck House. The Deck House was a housing type developed by architect Carl Koch. According to At Home With Tomorrow, he began his lifelong mission to create “the good, the beautiful, and the inexpensive” in housing while at Harvard under the guidance of Walter Gropius, who is famous for the development of the Modernist Movement in architecture. After the war, he turned his focus on the housing shortage, a symptom of the Great Depression, WWII, and returning Veterans with growing families and VA mortgage loan offers. His solution was for an affordable house of pre-fabricated parts to cut costs and provide streamlined construction. In 1953, his Techbuilt house was launched, after a decade of research. William Berkes and Robert Brownell had worked with Koch at Techbuilt after graduate school, but wanted to create a design of their own. They left Techbuilt in 1959 and founded Deck House, using the same principles. The exposed Douglas fir beams, wood panel ceilings and mahogany trim and window casements are what give the deck house a lot of its signature aesthetic. A wall of glazing, open floor plan with sloping roof rafters extending beyond the walls and a low placement in seemingly untouched nature are further elements that have endeared these houses to the modern homeowner.

Adin Wheeler House // 1790

The Adin Wheeler House is significant as a rare house form found in this part of New England. Located in Southbury, Connecticut, the property includes the main house, a barn, and the wheelwright shop, a barn-like structure. The house is a 1-1/2-story Cape style wood-frame structure, with a front porch across the front that is sheltered by a bell-cast extension of the main roof. This type of porch roof is uncommon in Connecticut, being reminiscent of Dutch rather than English construction methods. The dwelling was built for Adin Wheeler, who owned the millworks on the nearby falls with business partner Enos Candee, a business partner (and brother-in-law) whose house also stands nearby. Theodore Wheeler, Adin’s great-grandson, built the wheelwright shop in the late 19th century, as well as the major addition to the house, which served as a tap room and public meeting space. The property is a well-preserved collection of 18th and 19th century structures.

Benjamin Osborn House // c.1808

This charming cottage shows that you do not need a stately or elaborate house to have some serious curb appeal and house envy. This is the Benjamin Osborn House, located in Southbury Connecticut. The house was built in the early 20th century for newlyweds Benjamin B. Osborn and Sarah Stiles, who married in 1808. As a gift to the couple, Sarah’s father Ephraim Stiles, who lived in a house across the street, seemingly deeded a portion of his property for his daughter and son-in-law to build their family. Tragically, Sarah died one year later, possibly during childbirth. Benjamin would marry another of Ephraim’s daughters soon after… messy. The home is a four-bay Cape, with its off-center entrance sheltered by a Colonial Revival hip-roofed portico supported by Tuscan columns.

Oatman Hotel // 1806

It always amazes me that even getting lost driving the winding roads in obscure places, can reveal some of the most magical old buildings and history to uncover. This stunning Federal style mansion was built in 1806 and is located on the busy Southford Road in Southbury, Connecticut. The road was a span along a turnpike was the great thoroughfare between New Haven and Litchfield, Connecticut. Present-day Southbury was about halfway between the two, so lodging was always busy here. Knowing this, brother’s in-law, John Thompson and Benjamin Hurd had this turnpike hotel built to capitalize on the flow of weary travelers. Charles R. Oatman (1827-1904), who married Orinda T. Hurd, the daughter of Benjamin Hurd, acquired the property in 1870 and operated the hotel under his name as the Oatman Hotel. After successive owners, the name remained. It was sold in the 20th century and was converted back to single-family use, and maintains much of its original fabric, including a barn at the rear of the property. It could definitely use a new coat of paint!

Reuben Curtiss House // c.1840

The Reuben Curtiss House is a classic example of a Greek Revival farmhouse from the mid-19th century, located in Southbury, Connecticut. Local history states that a house built here by Israel Curtiss (1716-1795) who farmed the land with his large family. In 1798, Israel’s large estate was distributed among three of his sons, Joseph, Benjamin, and Reuben. This was complicated by the fact that in the same year, both Joseph and Benjamin died, leaving the entire estate to Reuben. From about 1840 and possibly until he sold the property in 1866, Reuben B. Curtiss ran an academy here, known as “Buck Hill Seminary for Boys.” It was a large operation, as suggested by the size of the addition and confirmed by the 1850 federal census. At that time there were 23 students in residence, ranging in age from 8 to 12, along with four adult supervisors. It was likely that the former farmhouse was expanded and the present 1840s Greek Revival block was added which now is the main facade.

Former Middlebury Central School // 1898

Having the tall order of being a neighbor to the later Westover School, the town of Middlebury’s Central School still packs an architectural punch. The school was built in 1898, replacing the former Union Academy building also near the town green. The school building is Neo-Classical in style with a projecting pedimented portico supported by four columns. A cupola extends through the roofline and shingle siding add some charm to the small two-room school building. The former school later housed the Middlebury Public Library and is now occupied by the Middlebury Historical Society.

Tranquility Farm – Superintendent’s Cottage and Creamery // 1894

Any good gentleman’s farm needs a superintendent to actually oversee all the labor being done to harvest crops and take care of the livestock (because a millionaire owner cannot be burdened to deal with such mundane matters…) When John Howard Whittemore, a successful industrial-era businessman purchased an old farm in Middlebury, Connecticut to spend summers and time out of industrial malaise, he knew that along with a summer home for his family, he would need to build other structures on the 300-acres of rolling hills. The famed architectural firm of McKim, Mead & White was hired by Whittemore to design many of the buildings on the grounds, from the main house, to the superintendent’s cottage to a boathouse. The firm designed this superintendent’s cottage (which currently looks to be getting a new roof) and the creamery in the rear. Both are great examples of the Shingle style in modest, agricultural structures.

Tranquility Farm – Farmhouse and Barn // c.1840

Tranquillity Farm, spanning the rolling hills around Lake Quassapaug in Middlebury Connecticut, was originally a 303-acre model/gentleman’s farm developed by John Howard Whittemore, a successful industrial-era businessman in Naugatuck, and his wife Julia Spencer Whittemore. Whittemore was a major figure in Naugatuck, sponsoring a series of commissions of McKim, Mead & White for buildings in the city center. For his country farm estate, he again commissioned McKim, Mead & White to design a new country house, a farm superintendent’s house, boat house on the lake, and other outbuildings for a working farm. An older farm was purchased, which included a modest Greek Revival style farmhouse dating to the early-mid 19th century (seen here) and a large wooden barn. Both of these were kept and incorporated into the estate near the southern entrance to the property, possibly to harken visitors back to the charm of rural living. The sweeping landscape, featuring miles of distinctive stone walls lining the roads and crisscrossing the fields, was designed by Charles Eliot and completed by Warren H. Manning – both protégée of Olmsted.

“Highfield” // 1914

The Highfield house is a historic building located in Middlebury, Connecticut. The House, surrounded by over 600 acres of land, was the former summer estate of Columbia University law professor Joseph and his wife, Elizabeth Chamberlain. They commissioned Theodate Pope Riddle, one of the first licensed female architects in America to build this comfortable English Arts and Crafts style cottage on a hill above a lake. It is likely that after the Westover School was completed in town, the Chamberlains were excited to see how Theodate could design them a summer house in the similar Arts and Crafts style. The estate was completed in 1914 and stands two-stories with the second floor concealed within the steeply pitched gable roof. Like Westover, the building was stuccoed. In the 1950s, the estate was purchased by a group of individuals who dedicated the complex as a family and country club with golf, tennis courts, and pool. It is known as the Highfield Club today.

St. John of the Cross Catholic Church // 1907

One of the more substantial buildings in the small town of Middlebury, Connecticut is this large church which faces the town green. In 1904 St. John of the Cross Parish was granted ecclesiastical status however, a decade would pass before the newly constructed stone church on the Middlebury Green was dedicated on November 22, 1914. The building was constructed in rubblestone with a Classical Revival temple-front pavillion and two Renaissance Revival square towers with open belfries. Reports stated that the building took over five years to construct, which was almost entirely built with volunteer labor and built with stones taken from parishioners fields. The architect of the church is unknown.

Westover School // 1909

At the heart of the rural community of Middlebury, comprised largely of Connecticut farmers, far from the hustle and bustle of the world, Mary Robbins Hillard (1862-1932) sought to create a girls school to “provide young women with a liberal education in a community which would contribute to the development of their character, independence and sense of responsibility.” To accomplish this, they needed a school, and Mary hired her good friend (and architect) Theodate Pope Riddle to design the private girl’s school campus and main buildings on a site fronting the town green. The school opened in 1909 with125 pupils, slightly over capacity. For the design Theodate Pope Riddle – who was one of the first American women architects and a survivor of the sinking of the RMS Lusitania – took inspiration from English Arts and Crafts and historical precedence in English schools with large open courtyard plans. Originally finished in a gray stucco, the building enclosed a quadrangle at the rear. Inside, administration offices, reception rooms, living rooms, a library, gymnasium, chapel, dining rooms, infirmary, and (of course) classrooms lined the interiors on a closed loop to allow students and teachers access to all parts of the building without ever stepping outside in the cold New England winters. The Westover School remains active and one of the highest ranked private schools in the area today, and with a more cheery yellow coat!

Former Middlebury Methodist Church // 1832

The oldest extant church building in Middlebury, Connecticut is a church that no longer is, the former Middlebury Methodist Church. Built in 1832, this building sits across from the Town Hall and Congregational Church and together, they form the eastern edge of the town green. The building is a more refined example of the Greek Revival style with paired entrances, corner pilasters, and a pediment facing the street with blind fan within. By the early 20th century, the church had a dwindling membership and sold the building in 1923 to the Westover School which opened just over a decade earlier. The building was used as a library for the school for some time and still is under the ownership of the esteemed private institution to this day, who maintain the former church very well.