Canterbury Center District School // c.1860

The Center District Schoolhouse of Canterbury, Connecticut, sits behind the village church and is the town’s best-preserved example of a district schoolhouse. Built c.1860, the vernacular, Greek Revival one-room schoolhouse served the central village through the 19th and into the 20th centuries with its twin entry, double-hung windows to allow light and air into the classroom, and a belfry with bell to notify pupils when class was about to start. Like many similar one-room schools in rural New England, pupils attended class with neighbors and siblings in the small, intimate classroom of varied ages. 

Samuel Pellett House // c.1752

The Samuel Pellett House in Canterbury, Connecticut, dates to the mid-18th century and is an excellent example of a Colonial-era home in this part of the state. Research in the land records suggests that this house may date from the time of Samuel Pellett’s second marriage in 1752 to Hannah Underwood. The couple planted two sycamore trees in front of the house to signify husband and wife but one was lost in the 1938 hurricane while the other survives to this day. According to historians, Sarah Harris Fayerweather, the first Black student at Prudence Crandall’s school nearby, worked as a servant in this house, then owned by Jedediah Shepard. The Pellett House is an excellent example of a Colonial Georgian home in Connecticut, with clapboard siding, center chimney, five-bay facade and small pane sash windows. 

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.


“The Pillars” // c.1780

Renovated in the early 20th century from a Federal style farmhouse, “The Pillars” in Canterbury, Connecticut, is an extravagant example of a Colonial Revival style residence in this quiet part of the state. The Pillars was the creation of Frank Edwin Miller (1856-1947) and his wife, Hattie Jenks Miller. The Miller’s retired here in 1913 after Hattie inherited the family homestead, which dated to the late 18th century, and they had the home renovated, adding the massive two-story columned porch and projecting entry. The house is a visual representation of the difference between Colonial and Colonial Revival styles as this home, the latter example, is a free interpretation of its prototype with exaggerated architectural details in a scale not seen centuries earlier.

Turnpike House // c.1810

This house in Canterbury, Connecticut, is known as the Turnpike House and dates to the early 19th century. A great example of a Federal style residence, the symmetrical, five-bay home exhibits pair chimneys, multi-light double-hung windows, and an elaborate center entry with sidelights and fanlight transom. The house was built along the Windham Turnpike (now Connecticut Route 14), which was an early toll road established in 1795. Behind the main block of the house is a squat gambrel-roofed ell, that is believed to be made from an older house that previously stood on this site, perhaps dating as early as 1745. According to tradition, this early house, which was also at one time supposedly used as a jail, was the home of Rev. Dr. James Coggswell when he ran a school for boys in Canterbury. One of his pupils at that school was Benedict Arnold, the infamous turncoat.

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.

Scotland Universalist Church – Shetucket Grange Hall // 1843

This charming, Greek Revival style building near the town green in Scotland, Connecticut, was built in 1843 as a Universalist Church for area residents who split off from more Congregationalist beliefs. By the end of the 19th century, populations shifted heavily to industrial centers where work was more plentiful, the church appears to have lost much of its membership and the building became a local grange hall. The Shetucket Grange was organized in June 1887, and was a meeting place for local farmers and their families to promote the economic and political well-being of the community and agricultural pursuits. Today, the building is owned by the town, but it’s use is unclear. Greek Revival in style, the building retains much of its original architecture, from its simple form, facade with two entrances flanking a central hung window, and pilasters framing the bays.

Edward Waldo House // c.1715

The Edward Waldo House in Scotland, Connecticut, is a vernacular Georgian house with saltbox roof and wings which from its erection about 1715 until 1971 was owned by members of the Waldo family. Edward Waldo (1684-1767) purchased land here along the Shetucket River in 1702 and by 1715, erected this house. The saltbox house which Edward Waldo built was one of the first houses in the town of Scotland and would remain in successive generations of the family for centuries. The house was the birthplace of Samuel Lovett Waldo (1783-1861), a portraitist who was a founder of the National Academy of Design as well as Daniel Waldo, chaplain of Congress, 1856-1858, and was one of seven Revolutionary War veterans who, having survived into the age of photography, were featured in the 1864 book The Last Men of the Revolution. The last Waldo owner, Miss Ruth Waldo died in1975. She insured the preservation of her family homestead by bequeathing the house, its contents, and about 15 acres of land to the Antiquarian & Landmarks Society of Connecticut Inc. and the surrounding acreage to the Connecticut Forest and Park Association, creating an enduring legacy for centuries to come. The house, set amongst a quiet country road, is evocative of early days in Scotland, Connecticut, and is one of the finest-preserved Colonial homes in this part of the state. 

Gallup Farm Carriage House // 1906

This handsome Shingle style building was constructed in 1906 as a carriage house of a larger farm property in Scotland, Connecticut. The barn is said to have been built for Archie Gallup, who purchased the old Manning farm just west of the town green in Scotland. The 1 1/2-story carriage-house with a gambrel-roof stands out for its principal entry of paneled wooden doors and above, a large, flared hood featuring two pedimented gable-dormers. The entire building is clad with varied shingles to add complexity to the design, catching the attention of all who drive by.