Seymour House // 1760

While this house appears to have been built in the mid-1800s as a Greek Revival home, it was actually built nearly a century earlier as one of the oldest extant properties on Main Street in Ridgefield, CT! Located on proprietors lot #20, the original building lots laid out for the new town of Ridgefield, this house appears to have been constructed in 1760 for Matthew Seymour (Seamore) and consisted of what is now the ell of the home (left side). Seymour operated one of the trade posts in town that engaged in trade with a nearby native Ramapo Tribe. The home was likely re-oriented and added onto with a more formal Greek Revival wing with its gable roof facing the street before the Civil War, a configuration it retains to this day.

Czar Jones House // c.1787

Czar Jones (1789-1869), a woodworker and a justice of the peace, served in the War of 1812 and later was a partner in the local carriage manufacturing company in Ridgefield, CT. Jones bought a circa 1787 house on Main Street in 1818 and modernized it to serve as his family’s residence. The modest late-Georgian house was updated in the Federal style. Not long after Czar’s death (his only wife died 1851) the home was then purchased by New York City publisher, Albert H. Storer and his wife Sophie, the latter was the founder and first president of the local Ridgefield Garden Club. The couple divorced in 1915, and Sophie moved to Europe before remarrying and settling in California. The home that was intended as a summer getaway for the family, became Mr. Storer’s primary residence as he remained in Ridgefield with his son Francis, daughter-in-law, and grandchildren, until his death in 1933.

Rockwell House // c.1850

Built in 1850, likely as a late-Greek Revival or Italianate style home, this property on Main Street in Ridgefield was completely “modernized” in the 1880s in the Queen Anne style popular at the time. The home was originally built for Francis Asbury Rockwell (1818-1881), a tin-smith, wine-maker and inventor who married Mary Lee Everest, who also had deep roots in the community and was a daughter of a local Revolutionary War captain. The couple built a home on Main Street and raised their children there until Francis and Mary died in 1881 and 1883 respectively. The family home was inherited by their eldest son, Charles Lee Rockwell, who became the director of the First National Bank in town. Charles updated the house to give it the Queen Anne Victorian flair we see today.

Lounsbury House // 1896

One of the (many) stately homes on Ridgefield’s Main Street, this massive Neo-Classical mansion is also among the most visited in Fairfield County. Lounsbury House was built in 1896 by former Connecticut Governor Phineas C. Lounsbury. While attending the 1893 Chicago World’s Fair, Governor Lounsbury was so taken by the Connecticut State Building that he built a replica to serve as his family home. The Connecticut State Building was designed by Waterbury-based architect, Warren R. Briggs at a cost of $112,000! Gov. Lounsbury loved this house, which he named “Grovelawn” until his death in 1925. After his death, his heirs were unable to maintain the massive home, and it started to decay. The Town of Ridgefield did not want to see the mansion demolished, and in an early example of historic preservation, the town purchased Lounsbury House in 1945. A school was built behind and nearly ten years later, the home was leased to the The Ridgefield Veterans’ Memorial Community Association. The home is now managed by a board and rented for weddings and community events.

King Mansion // 1894

After the American Revolution, Lt. Joshua King settled in Ridgefield and built the King Mansion in 1801, a Federal style home that commanded the Main Street lot. King was born in Bridgewater, Massachusetts and fought in the Revolutionary War near the border of Connecticut and New York. After the war, he settled in Ridgefield and married one of the most eligible bachelorettes in town Anne Ingersoll. Anne was the daughter of the Rev. Jonathan Ingersoll, pastor of the Congregational Church of Ridgefield. After a long life running a store and raising a family, Joshua died in 1839, a year after his wife. The mansion was inherited by their son Joshua Jr. until his death in 1887. In 1889, a fire destroyed much of the house. When it burned down, The New York Times described it as “the grandest old mansion in the village.” It was quickly replaced by the current house, modeled after the original but larger, which was placed much farther back from the road in the Colonial Revival style. Fire damaged the house again in the 1990s, and the present structure was restored and enlarged from 2002-2004, its HUGE!

Henry Smith House // c.1845

This stunning temple-front Greek Revival home on Main Street in Ridgefield, Connecticut is an absolute dream! The home was built in the mid-19th century for Henry Smith, who operated a shirt factory in town with his father. The house’s gable roof facing the street completes a pediment, which is supported by a projecting portico of four colossal Ionic columns. In the pediment, a gorgeous Palladian window adds so much character to the facade. I love a good temple-front classical home!

Keeler Tavern // 1713

Around the year 1713, Benjamin Hoyt built a home for himself and his family on Lot 2 of the laid out building lots along Main Street of Ridgefield CT. The building was originally a one room dwelling with a stone fireplace and no basement and was located next to the David Hoyt mansion (aka The Fountain Inn). After several years, he expanded the property by building around and above the structure, to give it the gambrel roof and size we see today. More than 50 years later, in 1769, the property was purchased by Hoyt’s son-in-law, Timothy Keeler. Timothy Keeler and his wife converted the building into an inn in 1772, just prior to the beginning of the American Revolutionary War. Keeler sided with the American revolutionaries and was active in the local militia. After the Battle of Ridgefield, British forces fired on the Keeler Tavern, because Keeler was an enemy. One of the cannons used to pummel the tavern is still lodged in a corner post of the house to this day. After later owners in the Keeler Family, the property was purchased by world-renowned architect Cass Gilbert, who turned it into his family’s summer home in 1907. In doing so, he made various improvements and additions to the building, in particular he designed a Garden House and added a sunken around the year 1910. Gilbert would also design a fountain as a gift to the town, which sits almost opposite his family’s summer residence. The property was purchased in the 1960s and has since been a historical museum.

The Fountain Inn // 1740

Located on Main Street in idyllic Ridgefield, in Fairfield County, Connecticut, The Fountain Inn provides one of the most welcoming and historical bed and breakfast experiences in New England! The Fountain Inn was built in 1740 as a “city home in the country” for David Hoyt, who showed off his wealth and stature in the young town by having such a high-style home built at the time. Decades later during the Revolutionary War, David Hoyt’s house became a part of the Battle of Ridgefield. After defeating the Colonial militia elsewhere on Main Street, British Gen. William Tryon‘s troops turned their attention to nearby Keeler Tavern, the local militia’s headquarters, which just happened to be neighbors with the mansion owned by David Hoyt, a known Loyalist. General Tryon’s troops practiced their artillery-firing skills on the building pummeling it with cannonballs, sending a message to the head of the local militia. David Hoyt formally demanded a cease-fire, as he was concerned about wayward cannonballs damaging his home. By 1790, with Ridgefield’s British influence diminishing by the day, David Hoyt finally left his Connecticut home and sailed back to England. The home was expanded and modernized over the next two hundred years until the present owners purchased the property and underwent a massive restoration of the Colonial house inside and out as their family residence. In the past year, the inn opened as the Fountain Inn so-named after a Cass Gilbert-designed fountain across the street.

Lillibridge Farmhouse // c.1770

Getting lost in New England is always fun because you can simply stumbleupon old farmhouses like this, which look like a setting of a movie! Located in northern Willington, CT, this farmhouse dates to the Revolutionary War! David Lillibridge (1744-1831) of Exeter, Rhode Island, served from 15 to 17 in the French and Indian War, and manned Fort Stanwix. In 1767, he was militia lieutenant, at the age of 25 converted, and entered the Baptist ministry. In 1777, he purchased a farm (unclear if there was a house on the land) from a Moses Holmes in modern day Willington and resided in this old saltbox Georgian home. The home remained in the Lillibridge family at least until the 1870s, when it was owned by Burnham Lillibridge. The house was moved from its previous location right on the street, and set back into the bucolic landscape, a fitting move!

Orrin Holt House // c.1840

Located on Tolland Turnpike in Willington, east of the Town Common, this temple-front Greek Revival home stands in an excellent state of preservation. The home was built for General Orrin Hatch (1792-1855) in about 1840 after his work as a member of the Connecticut State House of Representatives 1830–1832, and in the Connecticut Senate in 1835 and 1836. He was re-elected as a Democrat to the Twenty-fifth Congress, serving until 1839. After leaving Congress, he served as Inspector General of the Connecticut State Militia, until his death in 1855. He likely built this home after leaving Congress in 1839, in his hometown. There is something about a temple-front home like this, they are so stately!