Stories and Structures: Hubbard Woods Architectural Treasures

Stories and Structures: Hubbard Woods Architectural Treasures

Winnetka, Illinois 60093, United States

Created By: Winnetka Historical Society

Tour Information

Explore some of Hubbard Woods' historic architectural treasures! This 1-hour jogging or driving tour (or 1.5-hour walking tour) will take you from the historic Christ Church on Sheridan Road, through Hubbard Woods' historic downtown, along the border of Winnetka and Glencoe, and back through some of Winnetka's most picturesque neighborhoods. You'll learn about the architectural elements that make these structures unique, and hear stories about the people who lived and worked in them.

Free parking is available in the Hubbard Woods Station parking lot at 1180 Scott Avenue (behind Grace Nails before the Metra tracks).

The Winnetka Historical Society is a nonprofit charity recognized as tax exempt by the Internal Revenue Service under section 501(c)(3).

A donation will help the Winnetka Historical Society preserve our collections, maintain our facilities (Schmidt-Burnham Log House and Museum/Research Center at 411 Linden) and develop relevant and engaging programs.

For more information about the Winnetka Historical Society and to make a donation, visit our website at

Tour Map

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What You'll See on the Tour

The stories of Victorian houses at 254, 270, and 271 Scott begin with Jared Gage, a businessman turned banker who made his fortune running the first flour mill in downtown Chicago in the 1840s. Gage arrived in Winnetka in 1855, where he bui... Read more
Like many houses on the Village’s northern border, 15 Old Green Bay has a Winnetka address but is technically in Glencoe. This Georgian Revival house was built in 1909 for John Rogerson Montgomery II, an attorney who came from a long line... Read more
The house at 888 Tower is notable for its association with two of Winnetka’s most accomplished residents. The original owner was John Nash Ott Sr., a lawyer for First National Bank in Chicago. While quite successful in his own right, O... Read more
824 Prospect was originally built around 1898 for Henry Swanson, a “grinder” or cutlery salesman and his wife Anna. The Swansons were longtime Winnetka residents and lived in this house for four decades. Unfortunately, we don’t know w... Read more
The beautifully preserved Tudor Revival cottage at 800 Prospect was built in 1928 and designed by Spencer Solon Beman. Beman was the son of Solon Spencer Beman, the famed architect of the Pullman neighborhood in Chicago, the Pabst Building ... Read more
The shingle-style house at 822 Bryant was designed by Augustus Higginson in 1901. Born in Boston, Higginson studied architecture at Harvard and the Ecole des Beaux-Arts in Paris before moving to Winnetka in 1895. Higginson’s brother Georg... Read more
830 Sheridan Road is easily one of the most famous houses in Winnetka. This house, known as “Wayside,” is named after the tavern owned by John Garland, the first resident of the original portion of the house at 830 Sheridan. Originally ... Read more
A visit to a wayside tavern by weary pioneers on their long trek from New York to Wisconsin lead to the development of Winnetka’s first church, Christ Church. Those pioneers, John and Susannah Garland, arrived at the Patterson tavern in ... Read more
The beautiful eclectic home at 788 Walden may not look old, but the original structure is actually one of Winnetka’s oldest. This house was first build in 1875 by developer E. Ashley Mears, who has quite an interesting history on the Nort... Read more
This lovely Tudor Revival home was designed by Chicago-based architect Monroe R. Sandel in 1926 for attorney George A. Mason Jr. and his wife Louise. Mason was born in Chicago in 1902. After passing the bar exam, he went into business with... Read more
The beautiful Tudor Revival house at 777 Rosewood was built in 1929. The first owners of 777 Rosewood were John and Ruth Jirgal, who owned the house until Ruth died in 1950. The most significant person related to this house is not its origi... Read more
The beautiful Art Deco building at 925 Green Bay was designed by Puckey & Jenkins in 1927. They were notable architects in the Chicago area, designing several historic buildings in the city including the West City Trust & Savings Ba... Read more


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