The Tower Cottage // 1880

Tower Cottage was built in 1880 and is one of the best examples of Queen Anne architecture in the town of Ridgefield, CT. The home was designed and built by Charles Betts Northrup, a carpenter and builder who grew up in town. The home was eventually occupied as a summer retreat for Maude Bouvier Davis, who would spend some summers at the house away from the big city. In Ridgefield, Maude was sometimes visited by her niece, Jackie Bouvier, later known as Jackie Kennedy Onassis, First Lady to President John F. Kennedy. Maude owned the property until 1972 and the home has been lovingly preserved since.

Bailey-Keeler House // c.1860

Lewis H. Bailey (1818-1899) was a local banker, merchant, and hotel proprietor in Ridgefield, Connecticut. He had this stunning Italianate Villa home built on Main Street before the American Civil War. Bailey was savvy in realizing the upcoming development boom in town as wealthy New Yorkers began to arrive in town to build summer houses to escape the cramped city living and polluted air, and he began to sell off land and develop streets in the village. To house some shorter-term summer residents, Bailey constructed and operated the old Bailey Inn on a lot adjacent to his own home. The inn was torn down in the 1920s as the town’s dynamic as a summer town began to change with more more year-round residency. The Italianate Villa is a lasting legacy of Bailey and his impact on the town. The home with its square tower and detached carriage house are in a great state of preservation and significantly contribute to the character of Main Street.

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.

Rev. Thomas Hawley House // 1713


This old Georgian house was built in 1713 on the Proprietors Lot 5, on Ridgefield’s Main Street. Constructed for the first minister of Ridgefield, the home was originally occupied by 25-year-old Reverend Thomas Hawley (1689-1738) not long after his graduation from Harvard in 1709. In addition to being minister of the newly formed Congregational Church, Hawley (also spelled Hauley) also served as school teacher and town clerk. The house employs Dutch Colonial detailing from the gambrel roof to the extended portico over the front door, common in the Dutch colonies in the Hudson River Valley in New York.

Hawley House // c.1865

Located next to the Reverend Thomas Hawley House (last post), this gingerbread cottage on Ridgefield’s Main Street looks straight out of a fairy tale! The home appears to have been built around the Civil War (or a renovation of an earlier house) and blends Italianate and Gothic detailing elegantly under one roof. The home was built on land that was owned by the Hawley descendants and was occupied by a few members of the family until it sold out of Hawley ownership in the 20th century. The house was purchased in 2002 by Gregory and Valerie Jensen who restored the home. Mrs. Jensen is the founder of the Prospector Theatre, a non-profit cinema dedicated to providing a higher quality of life through meaningful employment to people with disabilities.

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.

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.