The Winchester Cultural Council awarded $12,055 in grants for 2025 to 15 individuals and organizations.  Funding for these grants came from the annual Local Cultural Council funding program of the Massachusetts Cultural Council and from the citizens of Winchester, through the Town of Winchester's own budget. Following is a list of the grants, in roughly chronological order.

• IN-visible Identities and INclusive Communities/Listening and Talking Across Differences (January and February 2025)
  To support a collaborative, two-part program by the Network for Social Justice in collaboration with Arlington-based True Story Theater. Part 1 is a two-hour public performance illustrating dimensions of personal identities, seen or not seen, that may affect feelings of belonging in our community. Part 2 is a two-hour facilitated workshop to practice active listening skills and learn frameworks for respectful dialogue.
• Children's Author and Illustrator Month (February 1, 2025)
  To support a visit by author Jannie Ho to read from her book, “Happy Chinese New Year,” to preschoolers at Winchester Recreation’s Kid Connection program as part of a student program exploring the process of creating and illustrating a story. The curriculum culminates with each child creating their own art based on what they have learned, to be displayed at an evening exhibition for their families.
• Chinese New Year celebration (February 2, 2025)
  An annual festival held at Winchester High School for everyone, organized and hosted for nearly 20 years by Winchester School of Chinese Culture, and now by Renaissance Chinese Culture Association.
• Hip Hop Chair and LINE Dance for Seniors! (February 2025)
  To support dance classes, one line dance and one chair dance, to clean-cut hip hop and R & B songs, conducted by MUSIC Dance.edu in cooperation with the Winchester Housing Authority. “All Aboard the Hip Hop Soul Train Express”
• Winchester History Sign (Spring 2025)
  To support an initiative by the Winchester Historical Society to replace the Winchester History sign next to Town Hall. After 25 years the sign is severely weathered and nearly illegible. Its replacement, in time for the Town's 175th anniversary, would include new images and content that better reflects the diversity of the community now and in the past.
• Biblical Archaeology with Nate Ramsayer (April 18 and 25, 2025)
  To support two presentations at the Jenks Center, the first on techniques of archeology of the ancient world (illustrated in part with artifacts from the speaker's personal collection), and the second a comparison of archeological results with the history related in the Bible.
• Griffin Terrace Series (May to October 2025)
  To support an outdoor summer concert series at the Griffin Museum of Photography produced by the Winchester Cultural District. The objective is to attract residents & visitors by highlighting local and diverse disciplines that are family friendly and free to the public. Supported by town funding.
• Winchester Porchfest (June 14, 2025)
  Porchfest is a unique, volunteer-organized, one-day community-building music festival where Winchester residents lend their porches as pop-up micro-stages to amateur musicians, who showcase their musical talent to neighbors, all other community members, and visitors from other towns. Supported in part by town funding.
• Vision(ary) 2025 (June to September 2025)
  A public art project conducted by the Griffin Museum of Photography, where fifteen cube structures fill the open spaces of downtown Winchester with images from local, national and international artists, communities and cultures. The 2025 exhibition will showcase our connection to the earth with portraits of the people and communities that surround us.
• Our Town (June to September 2025)
  A photographic essay about what makes a community, featuring the work of the local residents of Winchester and produced by the Griffin Museum of Photography. Residents of all ages are invited to submit images for display throughout town as part of the Vision(ary) project.
• Pop Up Art School Class Series (July 2025 to November 2025)
  For a series of hands-on art classes at the Winchester Public Library for teens (age 13+) and adults. Classes will cover clay sculpting, needle felting, acrylic painting, and watercolor painting, and attendees will leave each class with a finished project in hand.
• International Day at the Winchester Farmers Market (October 1, 2025)
  To support an annual celebration on the Common of the arts, music and dance of the diverse cultural communities in and around Winchester. In conjunction with the Winchester Farmers Market.
• Winchester Cultural District Sculpture Sponsorship (October 2025)
  To support continuation of the outdoor sculpture exhibitions along the Riverwalk in the Winchester Cultural District.  In October 2025, four of the six current sculpture leases will expire, and additional funding is needed to maintain the exhibition. Supported by town funding.
• Locke Family & Farm History (ongoing)
  For work by Winchester Archivist Ellen Knight of revising the 2008 publication, “The Wright-Locke Farm: A History in Pictures" to include recently donated images of the Locke family and the farm. The revised and expanded history could be posted at Winchester History Online or re-published in print form.
• Winchester's 175th Celebration (ongoing)
  For additional reporting by Winchester News Group on special events and programs commemorating Winchester’s 175th anniversary, and for historical reporting looking back at Winchester over those years. The additional material will include new and historical photography as well as interviews.