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.