City & town
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.
Taxes & budget
Jennifer E. "Jenny" McDonaldNo party listed
- Supports a financially and environmentally sustainable city future
Emily Rose WindleNo party listed
- Voted against tax increases during her first termIn office
Economy & jobs
Jennifer E. "Jenny" McDonaldNo party listed
No documented position found.
Emily Rose WindleNo party listed
- Opposed a proposed entertainment venue with a small casinoIn office
Roads & infrastructure
Jennifer E. "Jenny" McDonaldNo party listed
No documented position found.
Emily Rose WindleNo party listed
- Opposed setting a city stormwater fee
Health & human services
Jennifer E. "Jenny" McDonaldNo party listed
- Supports residents' access to resources and opportunities
Emily Rose WindleNo party listed
- Supports nonprofits serving residents facing rising living costs
Government & transparency
Jennifer E. "Jenny" McDonaldNo party listed
- Proposes empowering residents and neighborhoods
Emily Rose WindleNo party listed
- Supports greater transparency in city operations
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.