The first festival took place in 1969 and was held each year until 1984; following a ten-year hiatus festivals resumed in 1995. The event is organized as a fundraising event for the Hessler Neighborhood Association (HNA), which was formed in 1969 to save the neighborhood from being bulldozed to build student dormitories and parking lots for Case Western Reserve University. The proceeds are used "to preserve and maintain the neighborhood." 
The festival, which according to its website attracts more than 10,000 visitors, is held outdoors, on Hessler Road (which is blocked off for the festival). It typically includes arts and crafts vendors, vegetarian food, and street performances, as well as main stage performances of folk music, reggae, and capoeira.
Hessler Road, a small one-way residential brick street, is listed in the National Register of Historic Places and was declared a historic district by the Cleveland Landmark Commission in 1975. The nearby Hessler Court is the only remaining street in Cleveland with Nicolson pavement, a.k.a. wood block or wooden pavement.
In 2007 the Hessler Street Fair was not held, although a "Hessler Unplugged" reunion block party took place on Saturday, May 19, 2007. The Fair resumed on May 17-18, 2008.
The 2009 fair on May 16 and 17 marked the 40th Anniversary of the Hessler Street Fair. The fair was still being held annually as of 2017.