Captain John Clark House // 1802

The Captain John Clark House in Canterbury, Connecticut, is one of the finest examples of the Federal style of architecture in New England, and has remained in a fine state of preservation since its construction in the early 19th century. The house was built by 1802 for John Clark (1731-1834), who purchased an earlier home on the site from and had it either taken down or enlarged to its present appearance. The mansion is symmetrical with five bays, central entry and twin chimneys projecting through the hipped roof. The central bay is a showstopper with its triangular pediment at the roofline containing a fanlight, Palladian window at the second floor, and main entrance with its own pediment, sidelights, fanlight transom, all framed by two-story columns. The house’s south facade is equally beautiful with its own Palladian window and entrance.

Dr. Andrew Harris House // c.1820

This house is located across from the iconic Prudence Crandall House in Canterbury, Connecticut, and is another excellent example of a high-style Federal home in the town’s main village. Built in circa 1820, this residence was the home of Dr. Andrew Harris (1787-1840), one of two physicians in Canterbury in the early 19th century. After Dr. Harris’ death, the property was owned by Hiram and Nancy Waldo, who altered the house with the addition of a Victorian observatory at the rear, two-over-two sash windows, and an entry porch with paired door entrance.

Levally-Crandall House // c.1820

This attractive Federal-style Cape house is located in Canterbury, Connecticut, and is one of the very finest such houses of its type in the state. The house was built by William Levally, a successful millowner in town who married Patience Horton just prior. William died unexpectedly in 1841, and the property was inherited by Patience, who then married Hezekiah Crandall, also a millowner, who was also the brother of Prudence Crandall, the teacher who operated the famous African American girls boarding school in Canterbury Center in the 1830s. Hezekiah and his sister later migrated to Kansas, after essentially being pushed out of town. The Levally-Crandall House stands out for its proportions, exterior moldings, and ornate entry with pilasters, sidelights, and a molded, keyed arched transom. The house has been lovingly preserved by the successive owners, who clearly take pride in owning such a piece of history.

John Carter House // c.1765

One of the many stunning and well-preserved Colonial homes in Canterbury, Connecticut is this residence, the John Carter House on S. Canterbury Road. Records show that the house was built around 1765 for John Carter and his wife, Mary Smith. This house is a good example of the domestic architecture of 18th-century Connecticut and while there have been some changes over time, it continues to exhibit all the major hallmarks of the colonial type, such as a center-chimney plan, clapboard exterior, and five-bay facade. The house originally had a saltbox roof sloping to the rear, but was removed sometime in the 19th or 20th centuries, likely when the projecting Colonial Revival-era porch was added at the entrance. What a spectacular home!

Jacob Bacon House // 1794

In 1794, Revolutionary War veteran, Jacob Bacon (1754-1844), built this house on S. Canterbury Road outside the main village of Canterbury, Connecticut. The late Georgian/Federal style house features a large central chimney, symmetrical five-bay facade with center entrance, and a bold blue paint color. The house was seemingly built following Jacob’s 1793 marriage to a Martha Clark. Do you like the color of this house, or would you paint it something different?

First Congregational Church of Canterbury // 1964

The Canterbury Green has been home to four congregational churches in its history. Originally established in 1711, a modest frame church was built here and in 1736, a new meetinghouse was constructed as a more permanent building. The rustic structure was deemed insufficient for a wealthy rural community, so in 1805, a stately, Federal style edifice was built. Designed by Thomas Gibbs, a local architect/builder who also designed other nearby high-style Federal homes, the building was destroyed by fire in December, 1963. Within a year, this church was constructed on the ground of its 1805 building. While designed and constructed during the mid-20th century, the town clearly wanted its new church to contribute to the village’s Colonial character, having this Colonial Revival style church serve as the new anchor to the green.

William Moore House // 1803-2019

Formerly located at the intersection of two historic turnpikes in Canterbury, Connecticut, the William Moore House was a historic and architecturally significant residence that stood over 200 years until its demolition in 2019. The large, Federal style house was built in 1803 for William Moore, a merchant who operated a store and also served as the town postmaster. The upper floor of this house at one time accommodated a ballroom where the local Masonic organization met. Later in the 19th century, the house became the home of prominent merchant, banker, and politician Marvin H. Sanger, Connecticut Secretary of State from 1873 to 1876. In 1921, it was the home of Lillian Frink when she became one of the first women ever elected to the Connecticut General Assembly, along with four other women elected that same year. The house with its projecting center pedimented bay, elaborate corner pilasters on pedestals, and elegant Palladian window represented the height of country Federal-period architecture until destroyed by a fire in 2018, leading the town to raze the building a year later in 2019. The lot remains vacant as of 2025.

Prudence Crandall’s School for Young Ladies and Little Misses of Color // c.1805

Built c.1805 for Elisha Payne, this architecturally distinguished Federal style mansion in Canturbury, Connecticut is one of the most significant buildings in the state, not only for its architecture but historical significance. In 1831, a young white woman, Prudence Crandall, was asked to open a boarding school for girls in Canterbury. She purchased this mansion and began operations for the school, which was attended by many wealthy girls in town. In 1832, Ms. Crandall was approached by a young Black girl who worked as a servant in town, named Sarah Harris, asking to attend the school. Encouraged by conversations with both Harris and Maria Davis, a Black woman who worked for Crandall and shared copies of the abolitionist newspaper The Liberator with her, Crandall agreed to admit Harris. Almost immediately, residents protested the school’s admission of a Black girl and parents threatened to withdraw their students, Crandall undeterred, closed her school and reopened in 1833, solely for Black and Brown students. Young girls traveled from several states to attend the school. The legislature of Connecticut responded by passing the “Black Law,” which prevented out-of-state Black and Brown people from attending school in Connecticut towns without local town approval. Crandall was arrested, spent one night in jail, and faced three court trials before the case was dismissed. In September 1834, a nighttime mob of men attacked the house, smashing the windows, leading Crandall to close the school out of fear for her students as no protections were afforded to them. These events made national and international news in the 1830s and galvanized the burgeoning abolitionist movement. Crandall would later marry and left Connecticut, never to return. For her vision and brave actions at this school, Prudence Crandall is Connecticut’s official state heroine and the house was designated a National Historic Landmark in 1991.

George Washington Smith House // c.1886

This house on Westminster Road in Canterbury, Connecticut, is architecturally distinguished by its extensive and imaginative detailing, which reflects the widespread availability of manufactured architectural ornament in the Victorian period. The porch columns, archways, bay window, and round-arched windows all reflect an Italianate influence and the work of its original owner, Mr. George Washington Smith (1857-1937). The house dates to about 1886 when George W. Smith, built it from his workshop formerly located across the street. Smith manufactured mast-hoops, the wooden fixtures for attaching sails to the masts of sailing ships, and utilized his woodworking skills to build and decorate the exterior of his family home.


Asa Bacon Farmhouse // 1783

Located in northern Canterbury, Connecticut, this rural farmhouse was built following the American Revolution, showcasing the emergence of the Federal style from the Colonial Georgian type farmhouses before. The house dates to 1783 and was built by Captain Asa Bacon (1735-1819), a wealthy farmer and captain in the Revolutionary War. The home was also occupied by his son, Asa Bacon Jr. (1771-1857) a Yale educated lawyer who practiced law in town before moving to Litchfield. Asa Jr. was a turnpike promoter, advocating for turnpikes through the formerly sleepy agricultural town, opening it up to trade and commerce. The early Federal-period home features a five-bay facade and central entry with triangular pediment and fluted pilasters. The house appears much like it would have when originally built besides the Victorian-era two-over-two window sashes installed in the late 19th century. The farm even retains a few 19th century barns, likely built when the windows were replaced by later owners.