![](https://winchesterfirst.org/wp-content/uploads/2021/10/Main-Street-Winchester_2019-awards.jpg)
2019
Kentucky Main Street Awards
- Preservation Hero: Wendy & Peggy McAllister
![](https://winchesterfirst.org/wp-content/uploads/2021/10/Main-Street-Winchester_2018-awards.jpg)
2018
Kentucky Main Street Awards
- Spirit of Main Street: Graham Johns
- Best Main Street Event: Beer Cheese Festival
- Best Downtown Beautification: Courthouse Clock Tower Rehabilitation
![](https://winchesterfirst.org/wp-content/uploads/2021/10/Main-Street-Winchester_2017-awards.jpg)
2017
Kentucky Main Street Awards
- Best Promotional Event: Urban Loft Tour
- Best Volunteer: Debra Parr
![](https://winchesterfirst.org/wp-content/uploads/2021/10/Main-Street-Winchester_2016-awards.jpg)
2016
Kentucky Main Street Awards
- Best Main Street Partner: Greater Clark Foundation
- Best Event: ReMain North Better Block Winchester
![](https://winchesterfirst.org/wp-content/uploads/2021/10/Main-Street-Winchester_2015-awards_TopFiveMostRomanticMainStreetsPoster.jpg)
2015
National Main Street Center/
Main Street America
- Top 5 Most Romantic Main Streets in America
![](https://winchesterfirst.org/wp-content/uploads/2021/10/Main-Street-Winchester_2010-awards.png)
2010
The Winchester Sun Readers Choice Awards
- Most Community Involved Festival: Beer Cheese Festival
![](https://winchesterfirst.org/wp-content/uploads/2021/10/Main-Street-Winchester_2009-awards.jpg)
2009
Kentucky Main Street Awards
- Best Economic Restructuring: Loft Tour
![](https://winchesterfirst.org/wp-content/uploads/2021/10/Main-Street-Winchester_2004-renaissance-kentucky.jpg)
2004
Renaissance Kentucky
- Gold Level Community
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