Wynnedale is a town on the northwest side bordered by 44th Street, Cold Spring Road, 42nd Street, and 2400 West.
During the first half of the 19th century, a few farms sprung up near the bluffs overlooking . The Swift Family Cemetery, also known as Sleepy Hollow, dates back to about 1840. Some of the first settlers who owned farms in the area were buried there.
The 38th Street Bridge over the White River did not open until 1962. Before 1907, therefore, travel to Wynnedale from downtown Indianapolis involved crossing the river either at Washington, Michigan, or 10th streets before taking Cold Spring Road, then known as Meyers Free Gravel Road, north. After 1907, the 30th Street Bridge added another route. Meyers Free Gravel Road became Cold Spring Road in the 1920s.
In 1909, Thomas A. Wynne, who was instrumental in organizing the Indianapolis Light and Power Company in 1892, purchased 8 acres of undeveloped land for his personal estate. The Wynne home, built around 1905, was located at 2110 West 42nd Street. Other large homes located near the Wynne estate included the homes of automobile industrialist and entrepreneur James I. Holcomb.
Wynne purchased an additional 15 acres in 1922. When he died in 1924, the Wynne family subdivided the land, platted a new subdivision a few months later, and named it Wynnedale. At the time, there were three existing homes in the area. In 1926, new construction began. The community was designed to be exclusively residential. Winding tree-lined streets and distinctive streetlights set the tract apart from nearby areas.
In an effort to control development, residents met at Wynne’s home on 42nd Street in March 1939 and voted to incorporate. The corporate lines expanded in 1941 with the addition of 51.7 more acres of land, which were developed as the Colds Springs Heights subdivision. From the beginning, residents built homes in a variety of architectural styles, including Colonial and Tudor Revival, Bungalow, Prairie Style, and Spanish. Lot and house sizes were also varied. Homeowners in the 1950s and 1960s built ranch houses on undeveloped parcels.
When the 38th Street bridge over White River finally opened in 1962, access to the neighborhood became easy, yet the area remained secluded. Residents eager to keep out additional traffic blocked the county’s attempt to widen and pave Knollton Road as it cuts through Wynnedale. The town erected a barrier across the road in 1954 and then won a lengthy court battle to retain it at the time. Most homes in the Cold Springs Heights subdivision were completed after the bridge opened, between 1969 and 1986.
Under the 1970 city-county consolidation, Wynnedale is an . As such, it continues to hold elections for a town council and clerk-treasurer. Subdivisions north of 44th Street—Wynndale Estates and Wynnedale Heights—are not included in the town.
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