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Saturday, December 2, 2023 @ 9:00 am - 3:00 pm EST

Back after a four-year hiatus, Tiger Hollow’s always-anticipated house tour will offer a new experience in 2023: Tiger Hollow and the Ridgefield Historical Society are joining forces to present a Saturday tour of historic homes that will be preceded by a Friday evening gala preview party.

All the seasonal beauty of Ridgefield will be the backdrop for the Holiday Historic House Tour and Preview Party on Dec. 1 and 2.

Coinciding with the Ridgefield Holiday Stroll, the Preview Party and Historic House Tour will be a time for celebrating with friends and toasting the return of a traditional part of the holiday season. With the new schedule putting the house tour on a Saturday, the house tour committee will be able to accommodate more visitors during three two-hour time slots (9am, 11am, or 1pm) and will facilitate groups of friends being together to visit the homes. Early purchase helps assure a time slot and grouping.

The Houses

The selection of homes for 2023 highlights many aspects of Ridgefield’s history, from the first settlers to the late 19th Century “summer people.”

The Joshua King House, a home that has anchored a prominent corner on Ridgefield’s Main Street for centuries, was originally the home of Revolutionary War veteran Joshua King, who built it in 1801. King was Ridgefield’s first postmaster and the founder of King & Dole, a store whose building is now incorporated into the Aldrich Museum.  Although a fire in 1889 destroyed the original home, the King family rebuilt a very similar structure, set a bit further back from the street. In the early 20th Century, the property was sold to Richard Arbuthnot Jackson, whose family continued living there until the 1970s.

The Benedict House and Shop, listed on the U.S. National Register of Historic Places, was the modest home of a cobbler, who had his shop on the property. The house, built around 1740, backs up to a hillside where it’s believed a skirmish with British soldiers took place as the Battle of Ridgefield was winding down. The house and shop were extensively restored by architect Cass Gilbert, who bought the property in 1920. It was later the home of Robert and Mildred Wohlfor.

The Benjamin Keeler House dates to the pre-Revolutionary era and the early layout of the town: it sits on Proprietor’s Lot #25. The house was part of a large farmstead and remained in the Keeler family until the early 19th Century when it went into the Benedict family. One of its later owners was the Pulitzer Prize-winning author, Richard Kluger.

The Olmsted House is a handsome home 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 David Hoyt House, The Fountain Inn, sits on the east side of Main Street, facing the Cass Gilbert Fountain, donated by the famous architect. The original home on this site was built in 1740, on the Proprietor’s Lot #1, and featured in the story of the Battle of Ridgefield. Hoyt, a prominent loyalist, is said to have prevailed on the British to cease their attacks on his next-door neighbor, Timothy Keeler, whose tavern was a gathering place for the patriots. Hoyt’s motive was to protect his own home from stray fire, but after the war, he, like other loyalists, left the country for England. The Fountain Inn not only hosts overnight guests, but is also a venue for small gatherings and celebrations.

Preview Party – SOLD OUT

Before the tour, there’s the Preview, a chance to enjoy cocktails and heavy hors d’oeuvres at the beautifully restored Tuttle-Smith House, and an opportunity to support both Tiger Hollow Inc. and the Ridgefield Historical Society in a very convivial setting. The Friday, Dec. 1, event is limited in attendance and because alcohol will be served, no one under 21 can be admitted.

Tickets for both the Preview Party and the Historic House Tour will be on sale beginning Oct. 2 at the Ridgefield Historic House Tour website.


Stop at The Benjamin, 20 West Lane, for post-tour conversation with friends and lunch or a cocktail; they’ll contribute a portion of the afternoon’s proceeds to the two tour sponsoring organizations.



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