Winchester Main Street Community Meetings

We appreciate the active involvement of our Main Street Community! All year long, the Winchester Main Street Program is hosting monthly outreach and input sessions to engage directly with our community. These are intimate, open forum style sessions with guided topics. All sessions take place at 9:00 AM in the Zuckerman Room of Rouss City Hall unless otherwise noted.

To download the calendar as a PDF, click here.


February 16th: Meet the New Non-Profit
The new non-profit to administer the program has been officially chartered, and a memorandum has
been signed with the City of Winchester for a multi-year contract to carry out the Main Street
mission. Learn what this means for our community, and what our next steps are together.

March 15th: Q1 Round Table
We invite all stakeholders to join us in an open forum to reflect on Q1, check in, collect feedback,
and discuss our efforts for the months ahead. This roundtable may change based on the proposed
strategic plan schedule.

April 19th: Winchester Main Street Strategic Plan
Join the Main Street Board to review the proposed strategic plan, and learn about our proposed Four
Points committee structure.

May 17th: Winchester Main Street Mixer
Community leaders, non-profit leaders, business owners, organizers, and residents are all welcome
to engage with each other and learn about how Winchester Main Street is evolving.

June 14th: Q2 Round Table
We invite all stakeholders to join us in an open forum to reflect on Q1, check in, collect feedback,
and discuss our efforts for the months ahead.

July 19th: Christmas in July Discussion
We invite all business owners to attend and plan holiday activities with our community partners. We
would welcome a discussion about how to plan marketing, schedules, and the Holiday Market’s
return to Old Town.

August 16th: Winchester Main Street’s Master Plan
We invite all stakeholders and residents to share their wish lists for Old Town and welcome
community engagement to plan for the future improvements we need to be successful.

September 20th: Q3 Round Table
We invite all stakeholders to join us in an open forum to reflect on Q2, check in, collect feedback,
and discuss our efforts for the months ahead.

November 15th: 2025 Events Master Planning Meeting
Let’s take an opportunity to bring organizers from across the community together to set dates,
share resources, collaborate, and create a unified calendar with support from City staff and
Winchester Main Street, while considering community feedback, and look ahead to 2025.

If you have questions or would like more information, contact Winchester Main Street: mainstwin.kmbuzby@gmail.com

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