WinchesterNot a ballot

Voter guide · Nov 3, 2026

Winchester Mayor & City Commission Election 2026

5 of 5 council seats are on the ballot, with 10 candidates running. Updated Oct 5, 2026. Every claim links to its source. How we check

Not sure who to vote for? Answer 3 questions and see which candidates agree with you, and why.

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Nov 3Election Day

How to vote · 11 days left

Find where to voteCheck your registration
No-excuse in-person absentee voting begins (Oct 29): the election office's notice

These links go to official state and county election sites. Hours and rules differ by state; your election office has the final word.

The candidates

Listed alphabetically by last name. Every position links to its source.

Voters choose one mayor and up to four commissioners citywide.

No-excuse in-person absentee voting begins · Oct 29

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Also on your Nov 3 ballot

We research city races only. For these races, go to the state's official guide or a nonpartisan one.

Official voter lookupState voter guideVote411 (League of Women Voters)

Districts come from 2020 Census blocks and the district maps for this election. Your address decides your districts.

What the next council decides

01Downtown Main Street project4 sourced facts

Where it standsThe Main Street High Side renovation has reshaped downtown, and the mayor's race has centered on how the city handled its effect on businesses.

What's on the tableHow the city handles the remaining Main Street phases and any help for businesses disrupted by construction.

02Housing3 sourced facts

Where it standsHousing is a top goal of the commission's strategic plan, and the Lincoln Street redevelopment is the city's main housing project.

What's on the tableWhether and how the city uses incentives or its own projects to add affordable housing.

03Growth and development3 sourced facts

Where it standsCandidates describe Winchester as a growing city, with a major residential development underway on Boonesboro Road.

What's on the tableHow the city plans for new development, infrastructure and business recruitment.

04City budget and services3 sourced facts

Where it standsThe city sets its own tax rates each fall, and the mayor puts the city budget at about $27 million.

What's on the tableProperty tax rates, how to fund services such as police, fire and EMS, and how much to rely on grants.

3 notes on these statements

Logan Hall is listed as withdrawn from the 2026 Winchester City Commission primary, per the candidate on Facebook. WinCity Voices

Commissioner Shannon Cox is not seeking re-election to the commission; he ran for county judge-executive instead. Winchester Sun · Jan 11, 2026

Kenny Book served on the commission until losing a re-election bid and is now seeking a return. WinCity Voices · Apr 23, 2026

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Who matches you?

Answer any of these questions. We compare your answers with each person's sourced record, and nothing is stored. Questions where no one has a sourced record yet are left out. Tap a selected answer again to skip it.

  1. 1. When city construction disrupts downtown businesses, what should the city do?

  2. 2. What is the best way for the city to help make housing more affordable?

  3. 3. How should Winchester approach growth?

Seat the councilSeat the Council →Pick a winner for each open seat and see where the resulting council stands on each issue.On the recordHow the council voted1 council decision, each member's vote side by side, with a link to the minutes.New · How Winchester is runWho runs Winchester, and what it costsWho the city manager is, council pay, whether the city is in the red, and where your property tax goes.

Key dates

The seat math

0 stay (not up this year): 5 on this ballot

5 council seats. The council decides by a 3-vote majority.

  • The Winchester City Commission has a mayor and four commissioners, whose terms all expire December 31, 2026. City of Winchester
  • Winchester has a city manager form of government, and the mayor presides over the city commission and is a voting member. WinCity Voices · Sep 16, 2026
  • The commission's regular meetings are held at City Hall on the first and third Tuesday of each month. City of Winchester
  • The commission race is nonpartisan and at-large: voters vote for four. Ballotpedia
  • Ten commission candidates ran in the May 19 primary, and the top eight vote-getters advance to the Nov. 3 general election. WinCity Voices · May 20, 2026

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