Main Street High Side Project: A Transformative Downtown Revitalization for Winchester, Kentucky
Downtown Winchester has experienced a true transformation through the Main Street High Side Project — a major revitalization effort designed to enhance accessibility, walkability, and the overall visitor experience along Main Street between Broadway Street and Lexington Avenue.
Palmer Engineering is proud to have served as the engineering consultant for this impactful investment, working closely with The Allen Company, the project’s construction contractor, and the City of Winchester.
A Project Built on Community Vision & Economic Opportunity
The project focused on improving pedestrian access along the historic High Side of Main Street — the elevated sidewalk with steps — while supporting local businesses with enhanced storefront access and a more inviting streetscape.
In March 2022, Palmer Engineering presented the Winchester City Commission with a comprehensive design proposal including survey and GIS services, preliminary concepts, and final plan development.
Significant additional support followed. In October 2023, the project received a major investment when Rocky Adkins, Senior Advisor to Governor Andy Beshear, awarded $5.5 million to the City of Winchester—emphasizing the value and promise of the revitalization.
The City was also awarded a Transportation Alternatives Program (TAP) Grant totaling $4.44 million, an 80/20 funding match that enabled construction of the improvements.
These investments demonstrate a strong belief in Downtown Winchester’s long-term vitality.
Spring 2025
Construction activity on the Main Street High Side Project officially began in the spring marking the start of a transformational investment in Downtown Winchester. Crews quickly mobilized, and demolition advanced at a steady pace. By mid-April, approximately 90% of the High Side sidewalk, steps, and wall structures had been removed — signaling a major shift from demolition into reconstruction.
Key early work included:
Preservation of the historic five-globe lampposts, which were safely removed for storage until they could be reinstalled following construction
Installation of wooden access ramps at both Broadway Street and Lexington Avenue
Placement of Dense-Graded Aggregate (DGA) to form temporary pedestrian walkways
Relocation of water meters to the curb line for improved long-term infrastructure access
Preparations to begin forming new retaining walls and ADA-accessible ramps
With access maintained and the corridor prepared for new infrastructure, spring laid the foundation for rapid progress in the months that followed.
(Photo courtesy of the City of Winchester)
Summer 2025
By early summer, demolition work was largely complete — opening the door for rapid progress on retaining walls, ADA-accessible ramps, and pedestrian connections:
Walls and ramps began taking shape on the Broadway side, with excavation and utility relocations nearing completion.
Water meters and sewer laterals on the High Side were successfully relocated, with new pipe encasements installed to safeguard future work beneath sidewalks and walls.
Crews poured new concrete sidewalks, pedestrian stairs, and social stairs along the High Side.
Brickwork advanced throughout the project area, enhancing durability and visual character.
As construction progressed toward Lexington Avenue, key milestones followed:
The final retaining wall was poured near the Lexington Avenue end of the project.
Remaining High Side sidewalks were removed and replaced with Dense-Graded Aggregate, marking the final phase of excavation.
Work expanded to the Low Side, beginning with sidewalk removal near Broadway and asphalt backfill placement for curb footers.
Water meters along the Low Side — between The Happy Corner and High Speed Collectibles — were verified in good condition.
Traffic flow shifted from a temporary S-curve back to a straight alignment along the High Side, preparing the corridor for permanent operation.
Material selections — including colors for pavers, stamped brick, and decorative finishes — were finalized in coordination with the City of Winchester, ensuring downtown’s historic style remains cohesive. Plans for new handrails also moved forward.
With visible progress occurring across the entire project zone, Winchester residents witnessed the community’s long-anticipated vision for a safer, more accessible Main Street coming to life.
Fall 2025
As Fall 2025 arrived, the Main Street High Side Project progressed into its final phases — transitioning from major construction to finishing details that enhanced the beauty, accessibility, and the overall visitor experience.
City leaders, joined by teams from The Allen Company and Palmer Engineering, toured the construction zone in early September for a firsthand look. By that point:
All concrete work on the Low Side between Cleveland Avenue and Broadway Street was complete.
Additional concrete pours continued toward the Courthouse block and Lexington Avenue.
Paver installation began on the High Side, moving steadily from Lexington Avenue toward Broadway.
Custom handrails were being fabricated for installation before the end of the month.
Throughout October, most major construction activities wrapped up, with work shifting to the project’s finishing touches:
Landscaping, decorative elements, and final site restoration began.
Crews prepared areas for additional pavers and completed complex ramp work near Lexington Avenue.
Arrow Electric restored power and reinstalled decorative light poles.
Installation of benches, trash receptacles, and planters enhanced the welcoming streetscape.
Crews also worked diligently to prepare Main Street for new pavement — including milling, paving, and restriping — ensuring a smooth and safe roadway connection from Broadway Street to Lexington Avenue.
Winter 2025
By November 2025, the Main Street High Side Project had reached the exciting final phase of construction. Paving operations were underway, with fresh roadway surfaces placed throughout the corridor and striping scheduled for completion shortly afterward. The last pieces of handrailing arrived and were installed, while electrical crews worked diligently to complete wiring and reinstall the final decorative lamppost — restoring the familiar, historic glow of Downtown Winchester.
Landscaping progressed quickly, with benches and trash receptacles arriving to complete the welcoming and walkable public space. Final brickwork continued into early December, along with the remainder of pavement markings, including parking spaces and directional arrows.
As December arrived, the public could once again fully enjoy and experience the High Side of Main Street. New angled parking is now open, and benches are installed throughout the project area. Planters will be added in the spring to further enhance downtown’s vibrancy.
To mark this significant community milestone, the City of Winchester celebrated the project with a ribbon cutting before the Christmas parade on Saturday, December 6, 2025.
Following the celebration, crews will begin addressing the project punch list — a detailed set of final adjustments and verifications required to officially close out the project. This final step ensures every element of the improved streetscape meets the highest standards of quality and safety.
With the community once again strolling, shopping, and gathering along the High Side, the investment in Main Street is already achieving what it set out to do — strengthen the heart of Winchester for generations to come.
Check out the video below showcasing the transformation from summer construction to the finished project.