Oconomowoc, home to one of the first screenings of the Wizard of Oz in 1939 and to an abundance of lakes, sits halfway between Madison, WI and Milwaukee, WI. The city has played host to summer resort-goers since the 1870s.
Thanks to a collaboration between University of Wisconsin Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library, several great views of Oconomowoc’s downtown history are available for your perusal. Included also are images from Milwaukee Public Library.
View the Waukesha County History Collection and Milwaukee Public Library Historic Photo Collection for more images.
Long shot of parade on North Main Street in Oconomowoc. Crowds line both sides of Main Street. A float is passing 104 North Main Street. Awnings cover storefronts on the left side of the street. Electric lines and poles are on both sides of Main Street. Horses pull buggies in both directions on the street. UW Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library.
Medium shot of Forest Leaf’s Garage parade float for the Oconomowoc Frolic. The float has been made to look like a trolley car. A man with a beard and corn-cob pipe drives while two passengers sit in back. The passenger on the left is wearing a mask. Two boys look on from the sidewalk. UW Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library.
Medium shot of men shoveling in front of Leaf’s Garage at 104 South Main Street in Oconomowoc. Brick and stone buildings can be seen down Main Street. Electric poles line the street. UW Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library.
Exterior photograph of Motor Inn Garage in Oconomowoc. Garage doors are open and cars are parked on the street. The painted facade indicates this is a sales and service garage. UW Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library.
Long shot of East Wisconsin Avenue in Oconomowoc looking East from Main Street. The street is a dirt road. Cars are parked on the left. A horse-drawn cart enters the frame from Main Street. Electric poles and lines are on both sides of East Wisconsin Avenue. On the right side of the street, on the corner of Wisconsin and Main is a bank. In the background, a sign is hung across the street for Eastman Garage. Oconomowoc City Hall tower can be seen in the distance. UW Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library.
Long shot of North Main Street in Oconomowoc. Signs are hung across the street. The upper sign reads: “This way to the carnival.” The lower sign reads: “Oconomowoc Carnival Aug 3 and 4.” To the left, a sign hung on a pole reads: “Remember the baby show.” Cars are parked along North Main Street. UW Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library.
Long shot of Jones House in Oconomowoc. Trees obscure the first floor of the hotel, but Jones House sign can be seen over the entrance. Steam roller is parked on side of road with smoke puffing from the exhaust. Jones House was located at northeast corner of South Main Street and East Wisconsin in Oconomowoc. At the time of this photograph, Jones House was a year-round resort owned by Willam M. Jones. UW Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library.
Medium shot of the F. D. Bradley City Bakery in Oconomowoc. People pose on the plank sidewalk and inside the store window and door. The store has large windows with a prism glass transom. There are three keystone arch windows on the second floor. The facade has decorative brick patterns above the transom and at the cornice. A saloon is to the left of the bakery. Billboards and signs can be seen to the right of the bakery. UW Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library.
Close shot of Howard Hanson on a motorcycle in front of Hanson Brothers Meat Market at 107 Milwaukee in Oconomowoc. UW Digital Collections, Waukesha County Historical Society & Museum, and Waukesha Public Library.
This photo shows Baum’s Pharmacy in Oconomowoc. A sign on the side of the building advertises the interurban rapid transit service of the Milwaukee Electric Railway and Light (TMER&L) Company. Milwaukee Public Library.
View of a family of seven sitting on the porch of their house decorated for the 4th of July. Parents are in chairs. Three of the children are on the steps and the parents are holding the youngest two. Two flags hanging in front with patriotic banners draped around the porch. Milwaukee Public Library.
