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Ridgefield Holiday House Tour

The Olmsted House

This  handsome home was built on land purchased in 1923 by Frances M.  Olmsted, reportedly a distant relative of Frederick Law Olmsted, from  Julia Finch Gilbert, wife of the famed architect, Cass Gilbert. The  Gilberts owned large areas of land surrounding their country home, which  they called the Cannonball House and is now the Keeler Tavern Museum  and History Center. 

The Fountain Inn

What began in the early 18th Century as a more modest structure that survived the Battle of Ridgefield later became a grand home that is now The Fountain Inn. Believed to have been built about 1740 by David Hoyt on Lot #1 of the first Proprietors’ Lots, this home-turned-inn sits at the historic intersection of Main Street and West Lane, facing the Cass Gilbert Fountain.

The 1740 Benedict House and Cobbler Shop

The Benedict House and Shop, listed on the U.S. National Register of Historic Places, was the home of a cobbler, who had his shop on the property. A modest structure, sitting above Rockwell Road against the side of a hill, it’s described as comprising “two of the oldest surviving colonial buildings in Ridgefield.” The house was built around 1740, probably by Ensign James Benedict (1685-1762), on family land that was one of the original Proprietors’ Lots. 

The Benjamin Keeler House

The Benjamin Keeler House on lower Main Street was originally a one-and-a-half-story dwelling, built by Benjamin Keeler about 1756 on land that his grandfather, Samuel Keeler, had obtained as one of the original proprietors of Ridgefield, Lot #25. 

The Joshua King House

Joshua King first encountered Ridgefield as a Lieutenant during the Revolutionary War and later became one of its most prominent citizens. A native of Braintree, Mass., Lt. King was serving with the Second Regiment of the Light Dragoons near South Salem, N.Y., when the British spy Major John Andre was captured.

A Century-Old Colonial

This  handsome home was built on land purchased in 1923 by Frances M.  Olmsted, reportedly a distant relative of Frederick Law Olmsted, from  Julia Finch Gilbert, wife of the famed architect, Cass Gilbert. The  Gilberts owned large areas of land surrounding their country home, which  they called the Cannonball House and is now the Keeler Tavern Museum  and History Center. 

The Fountain Inn

What began in the early 18th Century as a more modest structure that survived the Battle of Ridgefield later became a grand home that is now The Fountain Inn. Believed to have been built about 1740 by David Hoyt on Lot #1 of the first Proprietors’ Lots, this home-turned-inn sits at the historic intersection of Main Street and West Lane, facing the Cass Gilbert Fountain.

The 1740 Benedict House and Cobbler Shop

The Benedict House and Shop, listed on the U.S. National Register of Historic Places, was the home of a cobbler, who had his shop on the property. A modest structure, sitting above Rockwell Road against the side of a hill, it’s described as comprising “two of the oldest surviving colonial buildings in Ridgefield.” The house was built around 1740, probably by Ensign James Benedict (1685-1762), on family land that was one of the original Proprietors’ Lots. 

The Benjamin Keeler House

The Benjamin Keeler House on lower Main Street was originally a one-and-a-half-story dwelling, built by Benjamin Keeler about 1756 on land that his grandfather, Samuel Keeler, had obtained as one of the original proprietors of Ridgefield, Lot #25. 

The Joshua King House

Joshua King first encountered Ridgefield as a Lieutenant during the Revolutionary War and later became one of its most prominent citizens. A native of Braintree, Mass., Lt. King was serving with the Second Regiment of the Light Dragoons near South Salem, N.Y., when the British spy Major John Andre was captured.