Hubbard Woods: A “Lakeside” Community

Gazette Article by: Barbara Sholl
Appeared in the Gazette: Winter 1996

The northeast section of Winnetka—Hubbard Woods—is named after one of the village’s founders and most prominent residents, Gilbert Hubbard. Born in Boston, Hubbard arrived in Chicago in 1849, when he and a partner started a ship chandlery business at 105 South Water Street. The men sold nets, twine, anchors and other necessities to Great Lakes sailors and fishermen.

Hubbard became a man of means and married the sister-in-law of Artemas Carter, the first president of Winnetka (1869-1873). In 1857, along with residents Jared Gage, Charles Peck and James Willson, he invested in Winnetka’s future by raising funds for the construction of a new train station at “Lakeside” (present-day Hubbard Woods).

In 1872, when the Great Chicago Fire destroyed his home in the city, Hubbard moved his family to a lakefront house at 575 Sheridan Road. The Hubbards also purchased land north of Tower Road (previously known as North Avenue) in an area which encompasses the ravines. Gilbert Hubbard served as Winnetka Village Treasurer from 1873-1878 and has been described as a man of “sterling character and high breeding.”

Hubbard Woods was the site of what Frank A. Windes, Village Engineer (1898-1940), called Winnetka’s “first and largest” building boom. The boom started in 1872, when Chicago real estate developer Ashley Mears built fourteen Italianate houses west of Green Bay Road and south of Tower Road. Only one of these houses remains today, located at 788 Walden Road.

Hubbard Woods is distinguished by the natural beauty of its ravines, the diverse and interesting historic houses that line its wooded streets, and its flourishing business district. A drive along Old Green Bay Road (once the Green Bay Trail) passes some beautifully preserved Italianate style houses built in the 1870s. Although many landmark buildings have been substantially changed, moved to other sites, or lost, some remain today. A house that has undergone considerable change over the years is at 1175 Whitebridge Hill. Built by Jared Gage in 1857, it served as an impromptu hospital and morgue for the victims of the shipwrecked Lady Elgin in 1860. Two delightful “twin” frame houses are located within a block of each other on Hubbard Street and Hubbard Place; both houses have been beautifully preserved. One was occupied by the Davis family, whose children made history when they flagged down a Chicago-bound train at Hubbard Woods using their grandfather’s red nightshirt!

The Green Bay Trail originally followed Sheridan Road through Winnetka, cut diagonally northwest—possibly along portions of Private Road—and then joined what is now Old Green Bay Road close to Hubbard Street. The first sturdy log bridge spanning the ravines on the Green Bay Trail was built sometime between 1845 and 1854. Located directly east of the Hubbard Woods train station, it was built by pioneer settler Anson Taylor, for whose family Taylorsport Lane is named. Stagecoaches travelled over this portion of the Green Bay Trail twice a week during the early 1800s.

Would Gilbert Hubbard recognize the area today? Certainly much has changed, but the community continues to thrive, much as it did more than one hundred years ago.

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5 Responses to “Hubbard Woods: A “Lakeside” Community”

  1. November 5, 2018 at 1:08 AM #

    My deceased wife worked for the Wheary family during the late 1950’s. The home was located on either Fisher Lane or Petticoat Lane. I am merely interested in locating the house on the internet. During that period, President Eisenhower visited either the Wheary family or their nearby relative’s home and my wife was involved in that presidential visit.

    Perhaps you can fill in the blanks for me.

    • November 5, 2018 at 11:47 PM #

      Hi Paul, in our historic phone directories, I’ve found a Rollin D. Weary Jr. at 936 Fisher Lane in 1957. It seems that the home there was demolished in the 1990s, so there is a newer house there now. I would be happy to send you information from our House Files. Thanks so much for reaching out to us — we’d also love to have more information from you about your wife and her experiences.

    • October 7, 2020 at 7:53 PM #

      I owned and lived at 936 Fisher Lane from 1983-1992. I understand one if the previous owners was the Wheary family.n I didn’t meet them but occasionally received mail for Cornelia Wheary. After I sold the house, it was demolished. I believe it was previously an auxiliary building in the Fisher estate.

  2. November 25, 2020 at 1:57 PM #

    My dad and his family lived at 988 Linden Ave., Hubbard Woods from the 20’s to the 50’s. I can’t locate the address, so I’m assuming that things have changed. Are there maps that date back to those times?

    • November 30, 2020 at 9:55 AM #

      Hi John, I’d be happy to look into this for you. We do have several maps that date back to that time. Feel free to send me an email at or fill out our research request form with a bit more information about what you are interested in!

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