City of Winchester, Kentucky

Rendering of a downtown street with historic storefronts, a white car, and landscaped sidewalks.

Rendering of a downtown street with historic buildings, parked cars, and wide sidewalks.

Rendering of a downtown street with historic buildings, parked cars, and a crosswalk in the foreground.

Rendering of a downtown street with historic buildings, a red modern building, and landscaped sidewalks.

Rendering of a downtown street with historic buildings, a crosswalk, and two people pushing a stroller.

Rendering of a downtown street with historic buildings and parked vehicles along the curb.

The Main Street High Side Project is a City of Winchester project to make improvements on the High Side of Main Street (the side with steps) between Broadway Street and Lexington Avenue.

The project will provide many benefits to the community, including access for all users, improved safety, mobility, business enhancement, historic enhancement, support of downtown activities, beautification and a destination area.

In March 2022, Palmer Engineering presented the Winchester Board of Commissioners with a proposal related to the design. The proposal was comprised of tasks that included survey/GIS, preliminary design concepts and final plan development. The total proposed and approved engineering fee was $256,000 with the fee divided at $116,000 (preliminary) and $140,000 (final). Monies to be utilized for this work included the current capital allocation for the Broadway Handicap Ramp ($125,000) and existing TIF monies (approximately $100,000).

In October 2023, Rocky Adkins, senior advisor to Gov. Andy Beshear, was in Winchester to award $4.44 million to the City of Winchester for the project through a Transportation Alternatives Program (TAP) Grant, with 80% of the project costs covered through the grant and 20% covered by the City. “These dollars … are not given; they’re earned,” Adkins said. “You all already have a great community and a great place, but what this does for you is give you that advantage you need to build the kind of community you want to build for the future.”

As such, the engineering work was initiated. Capital allocations have been reviewed for the Fiscal Year 2024/25 budget cycle to fund the remainder of the needed work. Comments from public meetings were compiled and incorporated into the design.

On Feb. 4, 2025, the Winchester Board of Commissioners approved a resolution entering into a Memorandum of Agreement (MOA) with the Kentucky Transportation Cabinet (KYTC) for the project. The MOA is a legally binding document that allowed the City to accept $4.44 million in TAP Grant funds for the project.

Sealed bids were first advertised Feb. 22, and were accepted until 2 p.m. Monday, March 17. At that time, city leadership opened and reviewed the bids to make a recommendation to the commission. There were three bids - $3.49 million, $3.58 million and $3.98 million. Palmer Engineering, the engineering consultant on the project, recommended the City accept the bid from The Allen Company.

At the March 18 meeting of the Winchester Board of Commissioners, a bid was approved for the Main Street High Side project. The bid was awarded to The Allen Company for $3.49 million.

Work on the project began in earnest in April 2025, with an anticipated completion in late 2025.

Want to receive email updates about the project? SIGN UP HERE.

Do you desire more information or have concerns about the project? Contact City Manager Bruce Manley at bmanley@winchesterky.com.

Are you a downtown business that desires an in-person meeting to discuss the project? Contact Whitney Leggett, director of strategic communications and downtown development, at wleggett@winchesterky.com.

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