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See the full calendar at finditwinchester.org/calendar. (View this content as a table)

Winchester Music Presents: A Night of Jazz

Fri, May 8, 2026 — 7:00pm

Winchester Music Presents: A Night of Jazz | Music, Dancing, & Dessert | Join us for an unforgettable evening at our annual fundraiser, featuring a toe-tapping night of music by the talented WHS & McCall Jazz Bands with special guests! | Friday, May 8, 2026 | Winchester High School Commons, 80 Skillings Road | All Are…

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Sponsors
Winchester Friends of Music
Winchester Public Schools
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Ripley Presents: Solar Winds and Impressions of Spring

Fri, May 8, 2026 — 7:30pm

- Solar Winds and Impressions of Spring, a compelling and inspiring program of music written especially for woodwinds.

Solar Winds bring music of the highest quality to recital halls and schools throughout the Boston area. The five musicians who comprise the heart of Solar Winds - a traditional woodwind quintet -…

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Venue
Ripley Chapel
Sponsors
First Congregational Church
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Annual Mother's Day Plant Sale

Sat, May 9, 2026 — 8:00am

Winchester Women's Lodge # 1593 Order Sons and Daughters of Italy in America. Proceeds allow us to continue to support our Community/Scholarship Fund ! We look forward to seeing you !! Thank you for your support.

Venue
Sons of Italy
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Shredding event & Savers donation drive - May 9

Sat, May 9, 2026 — 9:00am

Looking for where to donate clothes, fabric, linens, or books? Have shredding you want done? The Winchester Girl Scout travel group is raising money for our trips to Europe in 2027 & 2028 by offering some spring cleaning help on Saturday May 9 from 9 am to noon.

Shredding is donation per container (you decide the…

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Venue
Crawford Memorial United Methodist Church
Sponsors
Girl Scouts
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Wright-Locke Farm Spring Market and Seedling Sale

Sat, May 9, 2026 — 9:00am

Celebrate the season at our Annual Spring Market! This year’s event features our beloved seedling sale alongside a vibrant art fair showcasing handmade crafts and original artwork from local makers. Bring Mom for a relaxed day out, or pick up beautiful flowers and seedlings for the perfect gift. Enjoy fresh, locally…

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Venue
Wright-Locke Farm
Sponsors
Wright-Locke Farm
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Civics Action Project Showcase 2026

Sat, May 9, 2026 — 2:00pm

What do students learn in civics class these days? Come find out at the 2026 Civics Action Project Showcase! Students from McCall and Winchester High School will share their work researching and addressing current social issues important to them and their community. Students will present highlights of their research…

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Venue
McCall Middle School
Sponsors
League of Women Voters of Winchester
Rotary Club of Winchester
Winchester Foundation for Educational Excellence (WFEE)
Network for Social Justice
Winchester Historical Society
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Annual Charity Golf Tournament

Mon, May 11, 2026 — 11:00am

In addition to being our flagship fundraising event, the WSF Annual Charity Golf Tournament is one of the most enjoyable and popular spring events in Winchester. Held in May, golfers from Winchester and beyond eagerly dust off their clubs to start the season at the Winchester Country Club Golf Course, a Donald Ross…

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Venue
Winchester Country Club
Sponsors
Winchester Sports Foundation
Flier for Annual Charity Golf Tournament
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Indivisible Winchester Speaker

Mon, May 11, 2026 — 6:00pm

Title: From Exhaustion to Action: How Communities Sustain the Work of Democracy with Brian Corr

Indivisible Winchester (IndivisibleWIN) invites the community to a compelling event featuring renowned civic leader Brian Corr. Titled From Exhaustion to Action: How Communities Sustain the Work of Democracy, this…

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Venue
Winchester Unitarian Society
Sponsors
Winchester Unitarian Society
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Kids Graphic Novel Book Club

Tue, May 12, 2026 — 5:00pm

If you enjoy reading graphic novels, and you are in grades 3-5, this is the perfect book club for you! We will meet and discuss a different graphic novel once a month. Registration Required. This month we'll be reading. .. Bunnicula: The Graphic Novel by James Howe and Andrew Donkin.

Venue
Winchester Public Library
Sponsors
Winchester Public Library
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Second Tuesday Women's Reading Group

Tue, May 12, 2026 — 7:30pm

This month's book is Maid: Hard Work, Low Pay, and a Mother's Will to Survive by Stephanie Land. Copies of the book are generally available one month prior to the meeting and are located near the Reference Desk. Group members can call the Reference Department at 781-721-7171 x320 to have a copy reserved for themselves…

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Venue
Winchester Public Library
Sponsors
Winchester Public Library
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SpeakOUT Panel Discussion

Thu, May 14, 2026 — 7:00pm

Parent to Parent Winchester presents a panel discussion with SpeakOUT Boston, a nonprofit organization that supports LGBTQ+ community members and works to create positive change, will share personal stories. Ask questions and listen to honest, genuine, and heartfelt answers. Learn how to have safe, candid, and…

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Venue
Lincoln School
Sponsors
Parent To Parent
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2026 En Ka Fair

5/15/2026 to 5/16/2026

Come on down and join us for the annual En Ka Fair! Held in downtown Winchester/the Jenks Center parking lot.

Rides, fair food, the book tent, bake sale, jewelry, famous lobster rolls and more - all raising funds for En Ka Society.

More details will be given later!

Venue
Winchester Town Hall
Sponsors
En Ka Society
Rock the Smock: Flier for 2026 En Ka Fair
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Winchester Rotary Golf Tournament

Mon, May 18, 2026 — 10:30am

This tournament is held to benefit the Winchester Rotary Charitable Foundation, Inc.  The fund supports numerous local charitable organizations as well the national and international works of Rotary International.

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Venue
Winchester Country Club
Sponsors
Rotary Club of Winchester
Flier for Winchester Rorary Golf Tournament
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Monday Night Mystery Book Group

Mon, May 18, 2026 — 7:00pm

NOTE: Due to Memorial Day, this month's Mystery Book Group will meet on Monday, 5/18/26. Love mysteries? Join WPL for our monthly mystery book group. This month's selection is Pony Confidential by Christina Lynch. Copies of the book are generally available one month prior to the meeting and are located near the…

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Venue
Winchester Public Library
Sponsors
Winchester Public Library
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AANHPI Night!

Tue, May 19, 2026 — 5:30pm

NFSJ senior student interns Renee Lubormirski and Sonia Lakshmanan are leading the planning of a family-friendly Asian American Native Hawaiian Pacific Islander (AANHPI) celebration.

Join us Tuesday, May 19, from 5:30 - 7:30 PM at Winchester High School (80 Skillings Road) for activities with student clubs, performances…

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Venue
Winchester High School
Sponsors
Network for Social Justice
Flier for AANHPI Night!
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2026 Donnie Ellis Spring Draw Tennis Tournament

5/23/2026 to 5/25/2026
Venue
Packer-Ellis Tennis Courts
Sponsors
Winchester Tennis Association
Publicity image for 2026 Donnie Ellis Spring Draw Tennis Tournament
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Write On Winchester

Tue, May 26, 2026 — 7:00pm

Get your creative juices flowing at the Winchester Public Library's writing group. New and experienced writers are invited to the Library to explore creative writing in a safe, supportive, and inclusive environment. You'll have the opportunity to examine and apply writing techniques, to generate new work with writing…

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Venue
Winchester Public Library
Sponsors
Winchester Public Library
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Winchester PMC Kids Ride

Sat, Jun 13, 2026 — 9:00am

Annul bike-a-thon for kids ages 3-13 that raises money for Dana Farber/The Jimmy Fund. Volunteer opportunities 13+

Sponsors
Pan Mass Challenge
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Authorfest 2026

Wed, Oct 14, 2026 — 8:00pm

Authorfest delights Winchester students in all our schools. Winchester Foundation for Educational Excellence (WFEE) is proud to fund this annual event celebrating the love of books! Check out this article about Authorfest 2025: https://winchesternews.org/20251024_winchester-pitches-in-to-save-autho……

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Sponsors
Winchester Public Schools
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General State Election

11/3/2026 to 11/4/2026
Venue
Winchester High School
Sponsors
Winchester Town Clerk
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