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.

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.

Norton Mansion – Steinbach Hall // 1849

John Pitkin Norton (1822-1852) was a successful educator, chemist, and author, who at just 27-years-old, built this stately mansion on Hillhouse Avenue in New Haven, Connecticut, for his young family. John P. Norton studied chemistry under Benjamin Silliman at Yale College, and was eventually appointed Professor of Agricultural Chemistry at Yale in 1846. He helped to found the Department of Philosophy and the Arts at Yale College and authored many scientific papers, dealing with the chemistry of crops. Coming from an established family and beginning a successful career himself, John hired New Haven-based architect, Henry Austin, to design this large, Italianate villa. The window surrounds, canopies, and flamboyant Moorish entryway are typical of Austin, with the general form and detailing taking cues from architect Alexander Jackson Davis‘ work. The Norton Mansion was purchased by Yale University in 1923 and was long the home to the Yale School of Management and is now occupied by the Jackson School of Global Affairs.

Skinner-Boardman Mansion // 1832

One of the finest houses in New Haven is this stately residence, the Aaron Skinner Mansion on Hillhouse Avenue. The mansion was built in 1832 for Aaron Nichols Skinner (1800-1858) from plans by architect Alexander Jackson Davis. Skinner was a Mayor of New Haven (1850-1854), and for a short time, ran a boy’s boarding school out of this house. Skinner was also a CT State Representative, serving two terms. The house was originally built as a three-bay, two-story house with one-story side wings and a rear ell. After his death, the house was purchased by Judge William W. Boardman, who in 1859, modernized the property hiring architect, Henry Austin, who filled in the side wings and added Italianate window mouldings. The monumental portico supported by fluted, Ionic columns, creates such a stately presence for the early house on the street. In the early 20th century, the mansion was owned by Rutherford Trowbridge, who renovated the house for his own use. The house remained in the Trowbridge family until the death of his last daughter, Miss C. Rachel Trowbridge, when the estate became the property of Yale University.

General John Sedgwick House // 1860

The Major General John Sedgwick House is located in Cornwall Hollow, Connecticut, and stands out as one of the finest residences in this part of the state in a rural setting. The house was built by 1860 for General John Sedgwick (1813-1864), who was born in a house standing on this site, which had been built by his grandfather, a veteran of the Revolutionary War. In 1859, the Sedgwick family homestead burned to the ground. Sedgwick, then already well established in his military career, took leave to oversee construction of its replacement. This house was built, apparently on the foundation of the old house, in 1859–60. The work was done by Cyrus Marsh, a local builder, in the Italianate style with decorative brackets, window mouldings, hoods, and a large columned entry portico. Major General Sedgwick was active in many campaigns, and during the American Civil War, he was killed by a sharpshooter at the 1864 Battle of Spotsylvania Court House, he was the Union Army’s highest-ranking casualty of the war and never got to reside in his Cornwall home.

West Cornwall Covered Bridge // 1864

The West Cornwall Covered Bridge spans the the Housatonic River in the town of Cornwall, Connecticut and is one of three historic covered bridges in the state. Records indicate that a bridge was in this location as early as 1762, but many were destroyed by floods and storms over the years, and even in the past century, flooding as a result of the 1938 New England hurricane and the flood of 1955, threatened to wash the bridge away, but she survived. The 172-foot bridge has been depicted in paintings, photographs, and movies, including Valley of the Dolls a 1967 film. The charm of a historic New England covered bridge is so enchanting and has been a draw for tourists to stop by this amazing town for decades.

Birdsey Hall // c.1804

Built circa 1804 in the form of an English country estate house, Birdsey Hall stands as the finest property in the town of Goshen, Connecticut. The residence was built for Birdsey Norton (1763-1812), a wealthy cheese merchant who was said to have been inspired to build a country estate after travelling the American south on business. The high-style Federal/Adamesque mansion features expansive grounds bounded by brick walls and Victorian gardens. The property was later owned by Fred Favorite and Robert Devoe, friends of Liberace, who operated an antique store. Birdsey Hall remains one of the finest Federal estates in Connecticut.

Wright Homestead // 1767

This large, brick gambrel-roofed Colonial home in West Goshen, Connecticut, was built over decades beginning before the American Revolution and has remained in the same family ever-since! In 1767, Captain Jabez Wright (1737-1813) married Martha Baldwin of Goshen, and began constructing this farmhouse of brick. When the war broke out, he fought in New York, he also served as captain of a company of Connecticut militia, turning out to repel the British forces at New Haven. He would largely complete the home by 1787, and ultimately died in 1813. After successive ownership of generations of the Wright family, the property was owned by Henry G. Wright (1831-1917), a farmer who represented Goshen in the state legislature and held many town positions. The first Methodist sermons in town were also held in the home. Henry Wright died at 86 years old on this property, after being attacked by a bull. When entertaining guests, he showed others a prized bull, and possibly fell into the pen, and was trampled and attacked. The Wright Homestead is unique for its brickwork with bonds and burned headers, resembling many Colonial-era homes in Virginia, but this house can be found on the back roads of Goshen, Connecticut!

Old Goshen Academy Building // 1824

The former Goshen Academy building is located in the central village of the rural town of Goshen, Connecticut, and it is an important vestige of early education in the small town. The Goshen Academy building was built in 1824 from funds by shareholders of the institution. The academy featured a lecture room on the second floor with smaller classrooms downstairs. The academy would eventually close, and it has been occupied by the Goshen Historical Society.