CityScape announces plans for Wine on the WestSide, Fall Funfest

COOKEVILLE – CityScape has announced the highly-anticipated return of their live community events in 2021. Wine on the WestSide will take place Saturday, Aug. 14, 2021, and Fall FunFest is set for Friday, Sept. 10 – Saturday, Sept. 11, 2021. Both events take place in downtown Cookeville and showcase the city’s unique and historic commercial districts.

“We are overjoyed to bring these popular events back to the people of the Upper Cumberland,” said Holly Freeman, CityScape’s Executive Director. “Events like Wine on the WestSide and Fall FunFest are a key part of our ongoing mission to revitalize downtown Cookeville. They attract visitors to our area, boost the local economy and increase the overall quality of life for residents.”

Wine on the WestSide, one of Cookeville’s largest annual social events, is set for Saturday, Aug. 14. Now in its 10th year, the event expects to attract over 3,000 people to Cookeville’s historic WestSide district. Attendees can sample from a comprehensive selection of more than 125 wines and craft beers in all varieties, styles and price ranges. Portions of Cedar and Broad streets will be blocked off to allow patrons to sample at their leisure, listen to music from two stages and enjoy local food options. 

Tickets to Wine on the WestSide are on sale now and can be purchased by visiting General admission tickets are $45/person and non-drinker/Designated Driver tickets are $10/person. The event website also includes preferred hotel information and special rates, volunteer sign-ups and vendor applications.

Fall FunFest, Cookeville’s Main Street festival, will take place Sept. 10-11, 2021. Now in its 25th year, the festival features live music, WCTE’s Stations of Imagination, a Family Zone, 20+ food vendors and eclectic arts and crafts. Fall FunFest takes place on Cookeville’s downtown square around the Putnam County Courthouse and historically attracts 10,000-15,000 people over the weekend.

Thanks to generous civic partners and sponsors, admission to the community-wide event is always free. The hours are 5-10 p.m. on Friday, Sept. 10 and 10 a.m. – 10 p.m. on Saturday, Sept. 11. The full festival schedule and entertainment lineup will be announced at a later date. Vendor and sponsor information can be found at

Freeman continued, “2019 was a banner year for Fall FunFest. After COVID-19 caused world-wide event cancellations last year, we want to pick up where we left off, continue the momentum and make the 2021 festival a celebration of our community. Attendees will notice some changes and improvements, but can expect the same high-level, quality event they have grown accustomed to from CityScape. We can’t wait to share the weekend with you again. See you on the Square!”  

About CityScape
CityScape is a 501(c)(3) non-profit organization that works to preserve and enhance the historic downtown areas of Cookeville. Since 1991, CityScape has worked closely with city and county governments, individual business owners and merchants on renovation and expansion projects, as well as special events and campaigns that attract business to the area. CityScape places special emphasis on community livability, economic restructuring and historic preservation. Cookeville is proud to be an accredited Main Street community, which follows the proven downtown revitalization model developed by the National Main Street Center, a subsidiary of the National Trust for Historic Preservation.

More information about CityScape is available at or by calling (931) 528-4612.

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