Shaker Square is neither located in Shaker Heights nor shaped like a square, but ask for directions to the coffee shop at "Cleveland Octagon" and you'll most likely receive only confused looks in return. Shaker Square has always been shaped like an octagon. And Shaker Square is indeed located in the city of Cleveland, just west of its border with Shaker Heights. Strict zoning regulations originally prohibited the construction of apartment complexes and commercial buildings in Shaker. Thus, the dense residential neighborhood and bustling shopping center the Van Sweringen brothers developed would serve as a gateway to Shaker Heights, but remain apart from it.

The origins of Shaker Square date to 1922, when real estate developer Josiah Kirby purchased land along Shaker Boulevard from the Van Sweringens. Kirby began building the upscale Moreland Courts apartment complex and planned to build shops and more apartments, but he soon went bankrupt. The Van Sweringens subsequently reacquired the land and planned a retail development of their own, as well as a high-density residential neighborhood and the completion of the Moreland Courts. Their original intent, developed during the height of the streetcar era, was to place this shopping village inside Moreland Circle, a roundabout where South Moreland (later Van Aken) Boulevard split off from Shaker Boulevard. But this design did not leave enough room for automobile parking, so what might have remained a circle instead became an octagon – not a square.

Architect Philip Small – a favorite of the Vans who also designed their Daisy Hill estate and a series of Demonstration Homes on South Woodland Boulevard – designed Shaker Square with four buildings set around a "village green" which the Shaker Rapid ran through. Each building featured a two-story center section flanked on either side by a one-story wing. Small designed the buildings in the Georgian Revival style with red-brick exteriors, white trim, and slate roofs. After more than two years of construction, Shaker Square opened in 1929 as the nation's third-oldest planning shopping center (after Market Square in Lake Forest, Illinois, and Country Club Plaza in Kansas City). It contained a variety of high-end shops, restaurants, and professional offices.

After the construction of Shaker Square, Shaker Heights' zoning restrictions were eventually eased to allow apartments and shops in a number of areas of the city. Thanks to its rare status as one of Cleveland's only truly transit-oriented developments, Shaker Square remained a popular shopping and dining destination, and the apartment buildings surrounding it continued to attract residents. The Colony Theater opened on the Square in 1937. The Halle Bros. Co. opened its first suburban branch in a new building adjacent to the original Shaker Square in 1948.

However, the shopping district began to struggle with rising vacancy in the 1970s as a result of growing competition from suburban malls. The nonprofit Friends of Shaker Square (later Shaker Square Area Development Corporation) formed in 1976 and undertook the first of several attempts to revitalize Shaker Square. One of these efforts involved attracting national retailers, a controversial move that favored a wealthier clientele and seemed to ignore the total community that looked to this node. In 2000, Wild Oats Market, Chico, Ann Taylor Loft, and The Gap joined the locally owned Joseph-Beth Booksellers in a short-lived answer to mall competition, but within a few years these stores departed.

Beginning in 2004, a new owner, the Coral Company, operated Shaker Square for the next eighteen years, adding new signage and bringing in businesses that reflected the Square's location astride neighborhoods with increasingly divergent incomes. Popular restaurants such as Fire, Zanzibar, Yours Truly, Balaton, and Edwin's became a more important part of the retail mix, while a Dave's Supermarket and CVS Pharmacy ensured that the Square remained a vital resource for surrounding neighborhoods. The North Union Farmers Market further enlivened Shaker Square every Saturday during the growing season.

Despite its many bright spots, Shaker Square began to show the effects of deferred maintenance, and the COVID-19 pandemic precipitated a crisis that brought a district to the brink of foreclosure. In 2022, Cleveland Neighborhood Progress and Burten Bell Carr Development partnered to buy Shaker Square with plans to undertake its revitalization. As its centennial approaches, Shaker Square remains an essential space where the city and suburbs meet.

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Many residents of Shaker Heights know that the Van Sweringen brothers built the Shaker Rapid Transit in the early twentieth century to provide Shaker residents with quick and efficient public transportation service between their suburb and downtown Cleveland. Probably considerably fewer, however, know that more than a decade before the Shaker Rapid ran its first trains from Shaker to downtown Cleveland on April 20, 1920, the Van Sweringens had already created a public transportation system for Shaker Heights. That public transportation system, which also transported Shaker residents to and from downtown Cleveland, was the Shaker Lakes trolley line.

The story of the Shaker Lakes trolley line is the story of how the Van Sweringen brothers, unlike other Cleveland area developers of the early twentieth century, were able to successfully develop the 1300 acres of land in East Cleveland, Cleveland Heights, and Shaker Heights that was formerly the site of a colony of the United Society of Believers in Christ's Second Appearance, more commonly known as the Shakers. In 1889, the Shakers dissolved this colony and the land was sold. During the period 1892-1906, several local and out-of-state groups attempted to develop the land for single-family residential subdivisions. All failed, except the Van Sweringen brothers who succeeded largely because they were able to build a transportation system along Fairmount Boulevard that persuaded wealthy Clevelanders to move from Cleveland to Shaker Heights.

The story of the Van Sweringens' first transportation system begins In 1906, when the brothers, following the development model earlier employed by Patrick Calhoun in the latter's development of Euclid Heights, persuaded the Cleveland Electric Railway Company to extend its Euclid Heights trolley line along Fairmount Boulevard from Cedar Road to Lee Road, a distance of approximately two miles. In this venture, the Van Sweringens also employed the F.A. Pease Engineering Company to design an extension of Fairmount Boulevard. Three years earlier, in 1903, the Pease firm had designed the conversion of Fairmount Boulevard in Euclid Heights from a single lane dirt road into a grassy divided highway, making it, according to several sources, the first such highway in the United States.

By 1907, the Van Sweringens had completed construction of the Fairmount Boulevard extension and the Cleveland Electric Railway had laid trolley tracks on the Boulevard all the way to Lee Road. Just one year later, the Shaker Heights Land Improvement Company, which was controlled by the Van Sweringens, was already building and selling upper class housing on Fairmount Boulevard.

The Shaker Heights trolley line was the the fastest public transportation route from Shaker Heights to downtown Cleveland from 1907 until 1920. This was a critical period for the development of Shaker Heights. During this time, the garden suburb grew from a population of less than 200 to one of approximately 1,500 residents--a more than 700 percent increase in population.

For residents who boarded the trolley at its terminus at Fairmount Boulevard and Lee Road, the trolley trip to downtown Cleveland took an average of 45 minutes. When the Shaker Rapid opened in 1920, the trip to downtown Cleveland was significantly reduced. When the line was completed, travel time was only about fifteen minutes. While the Shaker Rapid supplanted the Shaker Lakes Line as the quickest public transportation route to downtown Cleveland, Shaker Heights would not have developed when it did and as it did were it not the vision of the Van Sweringens and the Shaker Lakes trolley line.

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