Loomis Homestead, Windsor, Connecticut

The Loomis Homestead, on the present-day campus of the Loomis Chaffee School in Windsor, probably taken around the turn of the 20th century. Image from Descendants of Joseph Loomis in America (1908).

The house around 1935-1942. Image courtesy of the Connecticut State Library.

The house in 2017:

Built sometime between 1640 and 1652, this house is the oldest in Windsor, dating back to the first few years of the town’s settlement, and it is also among the oldest existing buildings in the country. The house was significantly expanded later in the 17th century, but the oldest section – the ell on the right side – was built by Joseph Loomis, one of Windsor’s original settlers and the patriarch of the Loomis family in America. Loomis was originally a woolen Draper in Braintree England, but in 1638 he emigrated to the American colonies, along with his wife Mary and their eight children.

After a three-month voyage aboard the Susan and Ellen, the Loomis family arrived in Boston, and they lived nearby in Dorchester for the next year. However, in 1639 they joined a number of other Massachusetts colonists and relocated to the Connecticut River Valley. The following year, Joseph was granted 21 acres of land here in Windsor, located along the south side of the Farmington River, just to the west of its confluence with the Connecticut River. He built this house soon after, on a section of raised land that was known as “The Island,” because the surrounding meadows would often flood during spring freshets, effectively making the property an island.

Mary Loomis died in 1652, and Joseph in 1658, and their son John inherited the property. He had been about 16 years old when he and his family left England, and he lived here in Windsor until 1652, when he moved to Farmington. However, he moved back to Windsor in 1660, where he became a distinguished town citizen. He served as a deacon in the church, and he also represented the town in the Connecticut General Court from 1666-1667 and 1675-1687. John and his wife Elizabeth had eleven sons and two daughters, although only eight of their children would live to adulthood. Their only surviving daughter, Elizabeth, married Peter Brown, and they had a son, John Brown, who would become the great-grandfather of the prominent abolitionist of the same name.

According to the sign on the house, as well as other historical records, John Loomis built the main part of the house in 1688. He died the same year, but this addition was probably built for his son Timothy, who inherited the house and married his wife Rebecca the following year. They raised seven children here, and the youngest, Odiah, inherited the house. Odiah lived to be 88 years old, and after his death in 1794 he left the house to his son Ozias, who died two years later.

Ozias Loomis’s son, Odiah, was 12 years old when his father died, and he subsequently inherited the property, becoming the sixth consecutive generation to own this house. He and his wife, Harriet Allyn, had seven children, and, like his great-great grandfather Timothy Loomis, he represented Windsor in the state legislature, serving in 1818. However, he died in 1831 at the age of 48, and his youngest child, Thomas, inherited the house. Like his father, Thomas would also go on to be elected to the state legislature, serving in the lower house in 1857 and 1862, and in the state senate in 1874.

Census records from the late 19th century show Thomas Loomis as a prosperous farmer, with $20,000 in real estate in 1880. This included over 200 acres, although most of this was listed as unimproved woodland. He had 58 acres of meadows and orchards, and only two acres of tilled land, but in the year prior to the 1880 census his farm had produced 100 tons of hay, 624 pounds of butter, 800 dozen eggs, 80 bushels of potatoes, and 25 bushels of apples.

Thomas and his wife, Mary Jane Cooke, had two children, Allen and Jennie, although Allen died in 1884 at the age of 23. As a result, Jennie inherited the family homestead after her father’s death in 1895, becoming the eighth generation to own the house. However, Jennie was unmarried and had no surviving siblings, so in 1901 she transferred the house to the Loomis Institute, a private school that had been established in 1874 by five siblings from a different line of the Loomis family. The school itself would not open until 1914, but it was to be located here on “The Island,” where Joseph Loomis had originally settled in the 1640s.

The campus Loomis Institute, which later became the Loomis Chaffee School, was built just to the south of this house. Under the conditions of Jennie Loomis’s transfer of the house, she and her mother were allowed to live here for the rest of their lives. Mary Jane died in 1920, but Jennie was still living here when the second photo was taken around the late 1930s. She was actively involved with the school, serving as secretary of the Board of Trustees, and she lived here in this house until her death in 1944, about three centuries after Joseph Loomis had built the house.

The main section of the house underwent renovation in 1940, which included restoring the interior wood paneling to its original appearance. About a decade later, the older section was restored on both the interior and exterior, with the most noticeable change being the removal of the porch on the right side of the house. Otherwise, the exterior of the house has not significantly changed, and it remains a well-preserved example of 17th century saltbox-style architecture. It is still owned by the Loomis Chaffee School, and it stands as the oldest wood frame house in Connecticut, and the state’s second-oldest surviving building, after a stone 1639 house in Guilford.

George Warner House, Windsor, Connecticut

The house at 1006 Windsor Avenue in Windsor, around 1935-1942. Image courtesy of the Connecticut State Library.

The house in 2017:

This house was built in 1788, and was originally the home of George Warner. He was in his mid-20s at the time, and a few years later he married his wife, Abigail “Nabby” Mills. They had two children, who were also named Abigail and George, and the older George lived here until his death in 1827. Three years later, his daughter Abigail married Willard Loomis, and their first child, Walter, was born here in this house in June 1830, four months after their marriage.

Willard and Abigail had a second child, who was also named Abigail, but Willard died in 1840, at the age of 35. Walter was just 10 at the time, and within a year he had left school and was helping to support his family by working for farmers and brickmakers in the area. In 1845, when he was 15, the railroad opened through Windsor, and Walter was hired as the first station agent at the town’s depot. His responsibilities included selling tickets and handling baggage and freight, and he earned a salary of $5.50 per month. However, he did not care for the work, and after six months he returned to farming. By the 1850 census, he was listed as a farmer, and he was living here with all three generations of Abigails. His grandmother, Nabby, died the following year at the age of 79, but his mother was still living here in 1863, when he married Lucy M. Wilson.

In the 1870 census, Walter was listed as a farmer and a brickmaker, with real estate worth $5,010 and a personal estate of $1,760. His farm here included 50 acres of improved land, plus an additional 10 acres of unimproved land. His livestock included two horses, eleven head of cattle, and three pigs, and his farm produced 1,500 pounds of tobacco, 75 bushels of potatoes, 400 pounds of potatoes, and 30 tons of hay. At the time, he and Lucy had four young children: Edwin, Delia, Fanny, and Walter Marshall. They had one more daughter, Lucy, who was born in 1872, but the older Lucy died a week later, and the infant Lucy lived for only four months.

Throughout the 1870s, Walter continued to operate his farm here, with the 1880 census showing similar numbers of livestock and harvested crops. He also continued his brickmaking business, and in the early 1870s he even produced the bricks for Mark Twain’s house in Hartford. Walter’s mother Abigail died in 1879, at the age of 73, and a year later he married his second wife, Elizabeth B. Lincoln. However, tragedy struck again in 1881, when his 17-year-old daughter Delia died.

By the late 1890s, Walter and Elizabeth were living here with Elizabeth’s great aunt, Anna Maria Benton, who lived here under Elizabeth’s care until her death in 1898, at the age of 101. Around the same time, Walter’s youngest son, W. Marshall Loomis, married his wife Clara E. Nixon, and they lived here with Walter and Elizabeth for many years. Marshall continued the operation of the family farm, and focused primarily on tobacco and dairy products.

Walter Loomis died here in 1922, in the same house where he had been born 92 years earlier. Clara also died in 1922, at the age of 51, and Elizabeth died three years later. Marshall subsequently remarried to his second wife, Grace, and they were still living here when the first photo was taken around the late 1930s. He retired from farming in the late 1940s, when he was nearly 80 years old, and he proved to have his father’s longevity, living here in this house until his death in 1959, at the age of 90.

W. Marshall Loomis’s death ended four generations and over 170 years of his family’s ownership of this house. The property has not been an active farm in many years, and most of the surrounding area has since been developed as a suburb of Hartford. However, the house itself has not significantly changed since the first photo was taken around 80 years ago, and the house still stands as one of the many well-preserved 18th century homes in Windsor.

Oliver W. Mills House, Windsor, Connecticut

The house at 148 Deerfield Road in Windsor, around 1935-1942. Image courtesy of the Connecticut State Library.

The house in 2017:

This brick, Federal-style house was built in 1824, and was originally the home of Oliver W. Mills, who built it shortly before his 1825 marriage to Anna Phelps. Mills was a farmer, but he was also a brickmaker, and he produced the bricks that were used in the construction of his house. His was one of many small-scale brickworks that operated in Windsor during the first half of the 19th century, and by 1850 Mills employed three workers and produced 300,000 bricks per year. He and Anna went on to live here for the rest of their lives, and they had five children: Oliver, Helen, Mary, Alfred, and Arthur.

The younger Oliver inherited this house after his father’s death in 1866, and during the 1870 census he was living here with his mother, plus his wife Sarah and their two young children, Annie and Oliver. He was listed as a farmer, with real estate valued at $11,400 and a personal estate of $2,085, for a net worth of over $250,000 in today’s dollars. The subsequent census, in 1880, provides a more detailed account of the farm’s productivity, which included eight acres of tilled land, 22 acres of pastureland and orchards, and 100 acres of woodland. In 1879, the farm had a diversified output that included 400 pounds of butter, 800 dozen eggs, 100 bushels of corn, 30 bushels of rye, 200 bushels of potatoes, and 4,000 pounds of tobacco.

Sarah died in 1899, and Oliver in 1901, but the house would remain in the family for many more years. His son Oliver inherited the property, and lived here with his wife Catherine and their daughter Marguerite. Like his predecessors, he ran a farm here, but he also worked for many years for the National Biscuit Company, the company known today as Nabisco. Marguerite became a kindergarten teacher, and was later involved in a number of community organizations, ranging from the Windsor Historical Society to the Garden Club of Windsor. She and her parents were still living here when the first photo was taken, but Oliver died soon after, in 1943. Catherine died 10 years later, and Marguerite remained here as the fourth and last generation of the Mills family to live here, owning the house until her death in 1985.

Today, most of the former Mills farm has been developed. Logans Way, a short cul-de-sac, is now located directly behind the house, with an industrial development further in the distance. Just to the left of the house, high voltage power lines now cross the property. However, the house itself is still standing, and remains an excellent example of brick, Federal-style architecture. Very little has changed in its appearance since the first photo was taken about 80 years ago, and the house is now listed on the National Register of Historic Places.

Bissell Tavern, Windsor, Connecticut

The house at 1022 Palisado Avenue in Windsor, around 1935-1942. Image courtesy of the Connecticut State Library.

The house in 2017:

This house was built in the early 1790s for Ebenezer Fitch Bissell, Sr. and his wife Esther. They were in their late 50s at the time, and Ebenezer was a veteran of the American Revolution. In April 1775, he and a number of other Windsor men marched in response to the Lexington Alarm, and later in the year he was commissioned as a lieutenant in the 8th Connecticut Regiment. In 1776, this regiment became the 17th Continental Infantry, and Bissell was promoted to captain, serving until he was taken prisoner during the Battle of Long Island in August, 1776. Many American soldiers died in the appalling conditions of makeshift British prisons in New York City, but Bissell survived, and continued serving in the Continental Army after his release.

Ebenezer lived in this house until his death in 1814, and his wife Esther appears to have died around the same time. Their oldest son, Ebenezer, Jr., inherited the house, and operated it as a tavern. The house was located on the main route from Hartford to Springfield, so it was an ideal location for a tavern to serve the stagecoach travelers who passed through here. Variously known as Bissell Tavern and Bissell’s Stage House, the tavern was identified by a sign that featured portraits of Oliver Hazard Perry and James Lawrence, two naval heroes of the War of 1812. Ebenezer opened the tavern about a year after the end of the war, and by the early 1820s it was being run by his son, Fitch Bissell. He operated the tavern until about 1833, a few years before railroads would make the old stagecoach routes obsolete.

Although it does not appear to have been used as a tavern beyond 1833, the house remained in the Bissell family until 1841, a few years after Ebenezer’s death. For the rest of the 19th century, the property passed back and forth between the Bissell and Hayden families several times, but the house remained essentially unchanged on the exterior. By the time the first photo was taken, the house was owned by produce farmer Paul Kazanowski, and was listed as being only in “fair” condition in the WPA Architectural Survey. However, the house was subsequently restored, and today still it does not look much different from how it looked two centuries ago, when stagecoaches would stop here. It is now listed on the National Register of Historic Places, and it stands as the only surviving early 19th century tavern in Windsor.

130 Hayden Station Road, Windsor, Connecticut

The house at 130 Hayden Station Road in Windsor, around 1935-1942. Image courtesy of the Connecticut State Library.

The house in 2017:


The origins of this house are somewhat of a mystery, although it appears to date back to about 1760. It is several years older than the much larger Captain Nathaniel Hayden House on the right side of the photo, although both houses have matching brick, Georgian-style architecture. Nathaniel Hayden owned both houses, and there are several theories as to what this small cottage was originally used for. One possibility is that it was Hayden lived here for a few years before his larger house was completed in 1763, but a more probable explanation is that this cottage was used as his shop for his shoemaking business.

Like the larger house on the property, this cottage remained in the Hayden family for many years. Nathaniel’s grandson, Samuel Hayden, owned the property until his death in 1900. His only child, Lucretia, appears to have owned it until her death in 1918, but by the time the first photo was taken in the late 1930s, the property was no longer in the Hayden family. However, very little has changed in this scene, and both buildings are still well-preserved, more than 250 years after they were built. Because of this, both the house and cottage were individually listed on the National Register of Historic Places in 1988.

Captain Nathaniel Hayden House, Windsor, Connecticut

The house at 128 Hayden Station Road in Windsor, around 1935-1942. Image courtesy of the Connecticut State Library.

The house in 2017:

Brick colonial houses are not particularly common in rural New England, but the town of Windsor has an unusual number of such homes that are still standing. This particular house was built around 1763 by Nathaniel Hayden, whose great-great grandfather William Hayden had settled in this area of Windsor more than a century earlier. Nathaniel had grown up across the street from here in his father’s house, but when he was 24 he married Anna Filer, and the couple moved into this new house around the same time.

Like his father, Nathaniel was a farmer, shoemaker, and tanner, but he also served as a captain in the town militia. At the start of the American Revolution, he led a group of 23 Windsor men who marched out following the Lexington Alarm, and he later served as a captain in the Continental Army, where he participated in the Battle of Long Island. However, tragedy struck the Hayden family in early 1776, when Nathaniel’s wife Anna died, at the age of 35.

Two years after Anna’s death, Nathaniel remarried to Rhoda Lyman. He had no children from his first marriage, but he and Rhoda had four children together: Nancy, Nathaniel, Naomi, and Pliney. Nathaniel lived here until his death in 1795, at the age of 57, but the house would remain in his family for many years. Rhoda outlived her husband by nearly 40 years, and lived here along with the younger Nathaniel and his wife Lucretia, whom he married in 1808.

Nathaniel and Lucretia had five children, all sons, who grew up here in this house. Two of their sons, Nathaniel and George, moved out of this house after their marriages, but remained in the Windsor area. Two others, Edward and Uriah, traveled to California in 1849, seeking their fortunes in the Gold Rush. Like most of their fellow Forty-Niners, though, they only had moderate success. Edward would remain in California, but Uriah eventually returned east, where he lived in New York state.

Of the five sons, only the youngest, Samuel, remained here in the family house. He was only nine years old when his mother Lucretia died in 1831, but he lived here with his father and his uncle Pliney, eventually caring for both men in their old age. He married his wife, Sarah L. Halsey, in 1849, and they had one child, Lucretia, who was born in 1851 and named for her grandmother. Nathaniel died in 1864 at the age of 83, and Pliney lived here until his death 11 years later at the age of 89, after having been blind for the last few years of his life.

Lucretia married in the early 1870s, but was widowed at a young age, and by the 1880 census she was living here in this house with her parents. Samuel would remain here in this house until his death in 1900, and his wife Sarah died eight years later. Lucretia appears to have continued to live here for the next decade, until her death in 1918. She had no children, so her death marked the end of over 150 years and four consecutive generations of ownership by the Hayden family.

By the time the first photo was taken around the late 1930s, the house was owned by Willard Drake, a mason whose property also included the neighboring John Hayden House. At the time, it was already recognized as a historically-significant home, and very little has changed in this scene since then. Now over 250 years old, the Nathaniel Hayden House still stands as a good example of a brick, Georgian-style home, and it was added to the National Register of Historic Places in 1988.