In 1991, the concept of having an organization such as CityScape began with a group of concerned citizens who had the best interest of Cookeville's community at heart. Rita Craighead, Joe and Connie Albrecht, and city manager John Gentry decided that, with big-box stores such as Wal-Mart and Lowe's moving in, Downtown Cookeville needed attention. In 1992, to remain viable, Operation CityScape was incorporated, and in 1993, it achieved an IRS nonprofit status. The first director, Melinda Keifer, was hired in 1994, and the first office space, provided by Harold Jackson, was in the Arcade Building on Cookeville's courthouse square. Under Melinda’s direction, CityScape was certified as a Tennessee Main Street Community in 1995.
The first big undertaking was Phase I around the Courthouse Square in 1993. This project cost $587,000, with much of the work done in-house by the city. In addition, Elk Mountain redid the sidewalks, and Todd Masonry created the brick pavers at the corners. The first banner brackets went up at that time, as well. The "Lighting a Memory in Downtown Cookeville" campaign began. The campaign involved 54 lampposts around the Square, with a total of $27,000 being raised to offset the costs.
Participated in the City of Cookeville’s Downtown Infrastructure Improvement Project, and it obtained the services of Hodgson & Douglas, landscape architects, to establish a streetscape plan for Downtown Cookeville-Emphasis Area I.
CityScape's signature fundraiser, Taste of the Town, was first held in 1996 at the home of Dr. and Mrs. John Limbacher. The Limbachers hosted the 1997 and 2005 events, as well.
Other hosts were:
- 1997 - Dr. & Mrs. Limbacher
- 1998 - Dr. & Mrs. Walter Derryberry
- 1999 - Mr. & Mrs. Bobby Williams
- 2000 - Mr. & Mrs. Robert Lowe
- 2001 - Dr. & Mrs. Bob Bell
- 2002 - Dr. & Mrs. Chuck Jordan
- 2003 - Leslie Town Centre
- 2004 - Dr. & Mrs. Bob Bell
- 2005 - Dr. & Mrs. Limbacher
- 2006 - Dr. Walter Derryberry
- 2007 - Mr. & Mrs. Richard Newson
- 2008 - Mr. & Mrs. Parker Boles
- 2009 - Mr. & Mrs. Jeff Callahan
- 2010 - Mr. Greg Nabors and Charlotte Suggs-Nabors
- 2011- Mr. & Mrs. Richard Newson
- 2012- Ms. Betty Vaden
- 2013 - Dr. & Mrs. Phil Oldham
- 2014 - Salt Box Inn
- 2015 - Woody & Kari VanStratum
- 2016 - Dogwood Park
- 2017- Golden Eagle Golf Club
- 2018 - Cookeville's WestSide
- 2019 - The SaltBox
CityScape’s second annual event, Fall FunFest, was started in October 1996 to help celebrate Tennessee's bicentennial. Fall FunFest now takes place the first weekend of September each year around Cookeville's courthouse square.
In 2019, CityScape took over hosting Cookeville Wine on the WestSide - a local wine and craft beer festival that benefits local charities Genesis House and the Tennessee Rail Trail Authority. This event will take place annually down Broad St. and Cedar St. of Cookeville's Historic WestSide.