The small settlement of single-family homes huddled just south of the Stevenson Expressway’s Cicero exit may no longer be the swampy marsh it was when Dutch farmers arrived more than 120 years ago. But some residents still call the tiny hamlet in Garfield Ridge by its early name: Sleepy Hollow.
Built mere decades after the famous Washington Irving story about a headless spectral horseman, the three-block by four-block outpost has the quaint mix of single-family home styles that one would expect. Century-old workers cottages share space with simple ranch homes with matching painted gables and new brick two-flats.
According to lore, a quirky local mailman known only as “Tom” began calling the frontier community of Dutch, Polish, Czech and others Sleepy Hollow, and the name stuck.
When Fernando Vargas moved into his yellow 111-year-old two-story home on South Keating Avenue in 1980, the streets were dirt and there weren’t any sidewalks. But the area had charm. An old-timer who lived across the street told Vargas about how Al Capone’s west suburban operation functioned nearby and that one of his henchmen stood guard in Sleepy Hollow along the adjacent Chicago Sanitary Shipping Canal.
Vargas, 67, now finds himself to be the old-timer on the block as new families have arrived in the increasingly diverse area. “We still call it Sleepy Hollow, but there’s not many of us left,” Vargas said outside his home.
There are no plaques or markers to commemorate the tiny Southwest Side village, but Sleepy Hollow is itself a living remnant of the area’s early pastoral history when it was one of dozens of independent, free-standing communities that sprang up during Chicago’s 19th-century industrial boom. Each with its own early identities, local characters and points of interest.
The city’s current map of 77 communities and neighborhoods was created by the University of Chicago’s Social Science Research Committee in the 1920s and 1930s in an attempt to create order and identity and ease the census-taking process. But some old neighborhoods pop up in online maps, revealing glimpses into former lives.
One hundred and eighty years ago, the mostly rural area around Armitage and Grand avenues was known as Whiskey Point thanks to the saloon George Merrill opened to farmers and travelers out of his family home. Around the same time, a subdivision in north Lincoln Square became known as Bowmanville after a local hotel innkeeper and swindler who sold plots of land he didn’t own and skipped town. Nearby, a part of the North Center community was known as Bricktown for the brick quarries in the area. All three can still be found on online maps despite no longer existing.
Experts say every corner of the city is awash in defunct names and neighborhoods that disappeared. The names come from old settlements that preceded modern Chicago. Some were communities built on commuter transit lines in the rapidly expanding city. Others were the creations of real estate agents eager to create branding for new housing construction.
“It’s layers-upon-layers of names, often overlapping and in conflict with each other. All come from different origins, circumstances and periods of time,” said Tim Samuelson, the city’s emeritus historian, who has done exhaustive research on neighborhood names and how they came to be. It was a daunting task given how many cropped up across the city and how some disappeared completely while others lingered.
“The deeper you dig, the more you’ll find! It never ends. My head swims just trying to write this,” Samuelson said in an email.
Before annexation, city neighborhoods were more of an ethnic patchwork as thousands of immigrants arrived for jobs, and different ethnic groups carved out their own communities. The names were the immigrants’ attempt to re-create new homes based on their homelands.
“Some were originally named to reflect familiar places of origin for dominant immigrant ethnic groups, but the names can still solidly remain when the dominant population group changes,” Samuelson said, citing Pilsen, which now has a large Mexican population but was named by Czech immigrants.
Another example is South Shore, which was at one time subdivided into separate settlements with British names such as Essex, Bryn Mawr, Parkside, Cheltenham Beach and Windsor Park, reflecting the English heritage of immigrating British Illinois Central Railroad and steel mill workers. Some remaining markers include two Windsor Park train stations, Windsor Park Lutheran Church and streets such as East Cheltenham Place and Essex Avenue.
Some communities are remnants of large heavy-industrial settlements and factory towns, such as the Stockyards, Bricktown and Pullman, which remains a city neighborhood. While industry slowly eroded and workers moved away or died, the names remained. The city’s Southeast Side, a former industrial home of Chicago’s Southworks plant and various other factories, was divided into numerous areas such as The Bush, Irondale, Vet’s Park and Slag Valley.
“They disappear because people who use them disappear,” said Peter Alter, chief historian with the Chicago History Museum, who has worked with Samuelson. “Industries to which they’re connected disappear. Obviously, there’s no longer a steel industry on the Southeast Side.”
Some communities were the work of real estate agents who created new names or changed boundary lines “hoping to create a sense of place to an undeveloped area,” Samuelson said. In the early 1900s, a developer built nearly a dozen three-story apartment buildings on the east side of Winthrop Avenue, between Lawrence Avenue and Ainslie Street, thinking it would be a perfect place for newlywed couples. They christened the area Honeymoon Row, according to a 1903 Tribune article.
Retired antique map dealer George Ritzlin said a decade ago he and his wife — members of the Chicago Map Society — sold a century-old broadside advertisement with a map of Grayland, a large area between the Portage Park and Old Irving neighborhoods in the 1870s. It was the creation of real estate developer and Cook County sheriff John Gray, who owned hundreds of acres on the North Side and believed his community’s proximity to Chicago and the three railroads would be attractive to newcomers.
Today, only the Grayland station on Metra’s Milwaukee District North line remains.
Even some existing communities aren’t well-known. Chicago’s 50-acre LondonTown, for example, is not only a recognized neighborhood on the Far South Side, it’s also home to the London Towne Homes, a nonprofit co-op housing development of 803 townhouse units on land between Metra’s Electric Line, Gately Park and the Bishop Ford Expressway.
The community became a haven for middle-class African Americans in the 1960s. “It’s kind of like a little bedroom community,” said JoAnn Kenner, longtime president of the London Towne Homes, where she arrived as a 21-year-old newlywed in 1967.
“A lot of times, people don’t realize that we’re a housing cooperative — they think maybe we’re government subsidized, or a housing project or something like that … we’re totally member owned and operated.”
Other communities simply vanished in the growing city. Untold numbers of homes and businesses were bulldozed to make way for the area’s expressway circuit.
“The (neighborhood names) that are most fascinating to me at the moment are the ones where the neighborhood is completely gone,” Alter said. He cited “Black Bottom,” a Black working-class neighborhood located in the South Loop near the old Stanford Park before it was all demolished in the 1960s to make room for the Dan Ryan Expressway.
Neighborhood name changes, experts say, are inevitable as populations change or as sensibilities change. Business owners in Chicago’s gay nightlife district known as “Boystown” have rebranded the area Northalsted in a bid to be more inclusive and gender-neutral.
Vargas, a retired truck driver and handyman, said Sleepy Hollow will always be a part of him, adding that he’s turned down offers on his home, feeling comfortable in his small nook community despite its old age, isolated location and the fact his two adult children have their own homes.
He still enjoys the look of his block, from the alluring designs of the new construction to his next-door neighbor’s treehouse.
“I don’t want to sell. I’ve been here for 45 years. I want to die and let my kids decide what to do.”