The Cleveland/Bradley County Greenway was conceived in the late 1990s by a group of city and county leaders eager to provide a recreational venue that would appeal to all people. The first phase was a quarter-mile strip of asphalt between 20th and 25th Streets that was funded with a partnership between the City and County and business owners who believed in the concept of a greenway that could stretch between the Village Green Town Center and the Hiwassee River in Charleston. In 2005, Phase II, a mile-long stretch between 25th street and Raider Drive and funded by a grant from TDOT and was dedicated with a visit from Gov. Phil Bredesen. Two years later, Phase III, between 20th and Willow streets, was completed through another TDOT grant, followed by Phase IV between Tinsley Park and Mohawk Drive. This Phase was funded through a number of grants and contributions, including the County’s Healthy Community Initiative (HCI). Phase V, through Tinsley Park and completed in 2011, tied phases two and four together to form 4.2 miles of lighted, unbroken path that contains five pedestrian bridges and eight underpasses. In 2018, a spur originating off the greenway at Tinsley Park, was completed adding nearly a mile of connectivity to North Ocoee Street along Fillauer Branch. The spur was named the Casteel Connector for long-time Cleveland City Manager Janice Casteel.
In its first 20 years of development, the greenway spawned dozens of donations, including benches, trees, water fountains, restrooms, and structures. Greenway Park has developed off of Raider Drive and includes a playground, restroom, outdoor stage, pavilion, and 40-space parking area. Many running events, such as 5K races and the Cleveland Half Marathon utilize the greenway. Fund-raisers and other benevolent activities have found a stage on the greenway. And in its first two decades, the greenway received more than $3 million in grants from state and local governments.