We hear you loud and clear–or at least, we’d really like to! All year long, Winchester’s Main Street Program is hosting monthly outreach & input sessions to engage directly with you. These are intimate, open forum-style sessions with guided topics open to the public.

[All sessions take place at 9:00 AM in the Zuckerman Board Room of Rouss City Hall unless otherwise noted.]

[To download the calendar as a PDF, click here.]

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JANUARY 19 | Old Town Events 101

[*For Businesses and Organizers]

Learn how to host & promote your own events,  ask questions about City events, find out what to expect from the year ahead, or just speak directly with staff about event obstacles and troubleshooting.

FEBRUARY 16 | Understanding & Enforcing New Walking Mall Codes

[*For Residents, Employees, & Business Owners]

Hear directly from City staff across multiple departments to better understand the newly adopted changes to City code, how and when to report infractions, and what to expect from Police.

MARCH 16 | Q1 Roundtable

We invite all stakeholders to join us in an open forum to reflect on Q1, check in, collect feedback, and refocus our efforts and conversations for the months ahead. [*This meeting may change if emergent topics arise in Q1*]

APRIL 20 | The Future of Main Street: What Comes Next for Winchester

Join the Main Street Committee for the exciting first discussions regarding the future and development of Winchester’s Main Street Program as we share our road map for the next two years and the huge changes ahead!

MAY 18 | Community Coffeehouse: Who’s Who in Old Town

Community leaders, nonprofit leaders, business owners, employees, organizers, City staff–all are welcome to mingle at this targeted mixer intended to help you meet the people that make Old Town tick. Put names to faces or just learn about the groups and resources you didn’t know we had!

JUNE 15 | Q2 Roundtable

We invite all stakeholders to join us in an open forum to reflect on Q2, check in, collect feedback, and refocus our efforts and conversations for the months ahead. [*This meeting may change if emergent topics arise in Q2*]

JULY 20 | Christmas in July: Getting Ahead of the Holidays

[*for Business Owners]

It’s never too early to start! Discuss holiday events, promotions, and give us your own wish lists for Main Street with enough time to meaningfully make changes before the holiday rush sets in.

AUGUST 17 | Show & Tell: Drawing Inspiration from Other Communities – CANCELED

Listen to Main Street Committee members share the projects and features they’ve observed in other communities and help us brainstorm how to replicate them here–or bring your own examples from the places you’ve seen and loved!

SEPTEMBER 21 | Q3 Roundtable

We invite all stakeholders to join us in an open forum to reflect on Q3, check in, collect feedback, and refocus our efforts and conversations for the months ahead. [*This meeting may change if emergent topics arise in Q3*]

OCTOBER 19 | Annual Stakeholder Meeting – CANCELED

–TIME & LOCATION TBD–

NOVEMBER 16 | Come to the Table: 2023 Holiday Planning

Let’s take an opportunity to bring the community together to share resources and plans, collaborate, and lock in a unified event calendar with support from City staff and event organizers. The main topics of discussion for this meeting will be New Year’s events and Windependent Weekend.