Master Plan focus groups in 2018 identified the following as some of the issues, challenges, and historic/cultural needs facing Winchester today (see also the full document):
The Town of Winchester is writing a Master Plan that will guide development and community life for the next 10 years and beyond. The plan will have a big effect on our lives, and represents an exciting opportunity to both solve today's persistent problems and create a more beautiful town for tomorrow. Planning allows us to get the most out of what we do, and identify new things to do that can improve our lives as a community.
The previous Master Plan was written more than 65 years ago, and the lack of guidance for all that time has caused some problems.