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Winchester City Council

Second Ward

Vote for
1
Term
4 years
Candidates
2
Election
Nov 3, 2026

What this office does: The nine-member city council (the mayor and two members from each of four wards) sets Winchester's budget, tax rates and ordinances and appoints the city manager.

CandidatesCompare by issue

Jennifer E. "Jenny" McDonald

No party listed

Project manager, Loudoun County government

The gist

  • Proposes empowering residents and neighborhoods
  • Supports a financially and environmentally sustainable city future
  • Supports residents' access to resources and opportunities
More about Jennifer
View sources (1)

  1. Proposes empowering residents and neighborhoods

    McDonald enters race for Ward 2 seat on Winchester's City Council

    News coverage · The Winchester Star · winchesterstar.com

    “her political platform focuses on empowering residents and neighborhoods, building stronger community connections”

  2. Supports a financially and environmentally sustainable city future

    McDonald enters race for Ward 2 seat on Winchester's City Council

    News coverage · The Winchester Star · winchesterstar.com

    “ensuring a financially and environmentally sustainable future for the city of Winchester”

  3. Supports residents' access to resources and opportunities

    McDonald enters race for Ward 2 seat on Winchester's City Council

    News coverage · The Winchester Star · winchesterstar.com

    “should feel welcome, connected to your community and have access to the opportunities and resources you need to thrive”

Emily Rose Windle

No party listedIncumbent

Legislative assistant, Virginia General Assembly

The gist

  • Opposed setting a city stormwater fee
  • Supports greater transparency in city operations
  • Supports nonprofits serving residents facing rising living costs
  • Voted against tax increases during her first termIn office
  • Opposed a proposed entertainment venue with a small casinoIn office

In office = from the candidate's own official statements or legislation as an officeholder, not their campaign.

More about Emily
View sources (2)

  1. Opposed setting a city stormwater fee

    Windle to seek reelection to Ward 2 seat on City Council

    News coverage · The Winchester Star · winchesterstar.com

    “she fought against setting a stormwater fee to help cover improvements to Winchester's infrastructure”

  2. Supports greater transparency in city operations

    Windle to seek reelection to Ward 2 seat on City Council

    News coverage · The Winchester Star · winchesterstar.com

    “She also has pushed for greater transparency with city operations and decisions.”

  3. Supports nonprofits serving residents facing rising living costs

    Nonprofit Collaborative hosts forum for City Council candidates

    News coverage · The Winchester Star · winchesterstar.com

    “Windle characterized nonprofits as being critical to Winchester, particularly because the cost of living has risen dramatically over the past decade”

  4. Voted against tax increases during her first term

    Windle to seek reelection to Ward 2 seat on City Council

    News coverage · The Winchester Star · winchesterstar.com

    “She has consistently opposed tax increases”

  5. Opposed a proposed entertainment venue with a small casino

    Windle to seek reelection to Ward 2 seat on City Council

    News coverage · The Winchester Star · winchesterstar.com

    “as well as a proposal for the construction of an entertainment venue with a small casino component in the city”

Challengers are listed first and incumbents last; otherwise candidates appear in ballot order. The Gist does not rank, rate or endorse candidates. Only positions backed by a cited source are shown; 5 issues covered in this race.