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

Winchester Artists Town Day Exhibit

Sat, Jun 6, 2026 — 9:30am

Come to Town Hall on Town Day to see beautiful artwork by Winchester artists who are members of the Winchester Artists' Network. You can meet many of the artists at a reception in Town Hall's beautiful and historic Winchester Room on the first floor throughout the day. Art will remain on display throughout the…

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Venue
Winchester Town Hall
Sponsors
Winchester Artists Network
Winchester Cultural Council
Winchester Room, site of the Winchester Artists Town Day Exhibit
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Town Day Beer and Wine Garden

Sat, Jun 6, 2026 — 3:00pm

FREE to attend! Join us as we wrap up Town Day 2026 with an unforgettable afternoon at the Town Day Beer Garden! Enjoy locally crafted beer poured by Arlington Brewing Company, wine from Marble Ridge Winery, and live music by Scott Damgaard -- all set on the beautiful outdoor terrace of The Griffin Museum of…

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Venue
Griffin Museum of Photography
Sponsors
Chamber of Commerce
External flier or other event image
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Live Watercolor Demonstration with Carolyn Latanisian

Sat, Jun 6, 2026 — 6:00pm

Winchester artist and teacher Carolyn Latanisian will be present to demonstrate her art in a special session. Registration opens in the last week of May at www.jenkscenter.com.

Venue
Jenks Center
Sponsors
Jenks Center
Flier for Live Watercolor Demonstration with Carolyn Latanisian
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Garden Tour with Jess Zander

Sun, Jun 7, 2026 — 12:00pm

Jess Zander of You Can Do It Gardening will gibe a tour of her native garden as a fundraiser for the farm.
(afternoon, timing TBD)

Venue
Wright-Locke Farm
Sponsors
Wright-Locke Farm
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PRIDEfest 2026!

Thu, Jun 11, 2026 — 4:30pm

Winchester's 6th annual PRIDEfest will take place in the Winchester Town Common on Thursday, June 11th, 4:30-6:30PM (rain date Friday, June 12th, same time). This is an outdoor, community-centered, Winchester-based event featuring multiple ways for attendees to educate themselves about LGBTQIA+ rights and issues and…

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Venue
Town Common
Sponsors
Network for Social Justice
Flier for AANHPI Night!
External flier or other event image
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An Evening with Isabella Stewart Gardner

Thu, Jun 11, 2026 — 6:00pm

The well-known art collector, philanthropist, and patron of the arts Isabella Stewart Gardner visited Winchester in 1915. Now modern Winchester residents have the opportunity to meet her, as portrayed in period costume by Jessa Piaia. Mrs. Gardner  will reminisce about her visits to artists here and on the North Shore…

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Venue
Griffin Museum of Photography
Sponsors
Jumelage Association
Flier for An Evening with Isabella Stewart Gardner
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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
External flier or other event image
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Destress with Grant the Therapy Dog

Mon, Jun 15, 2026 — 5:00pm

This event is for students in grades 6-12. No adults, please. Stressed out? Finals, studying, and projects all you can think about? Why not take a quick 15 minute break and come pet Grant, a therapy dog! The slots are open to three people at a time so come with friends.

Venue
Winchester Public Library
Sponsors
Winchester Public Library
External flier or other event image
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2026 Chamber Annual Garden & Outdoor Living Tour

Tue, Jun 16, 2026 — 12:00pm
Sponsors
Chamber of Commerce
External flier or other event image
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Summer Reading Kickoff: Foam Party on the Lawn!

Tue, Jun 16, 2026 — 3:30pm

Join us out on the Library Lawn to officially kick off our Summer Reading Program! Sign up to play in the foam on the lawn and also stop by one of the Summer Reading Tables and sign up for our Summer Reading Program. This program is for preschoolers age 4 and up - students entering 6th grade.

Venue
Winchester Public Library
Sponsors
Winchester Public Library
External flier or other event image
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Monday Night Mystery Book Group

Mon, Jun 22, 2026 — 7:00pm

Love mysteries? Join WPL for our monthly mystery book group. This month's book is Djinn Patrol on the Purple Line by Deepa Anappara. Copies of the book are generally available one month prior to the meeting and are located near the Reference Desk. Please email Kristin at kmacleod@minlib.

Venue
Winchester Public Library
Sponsors
Winchester Public Library
External flier or other event image
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VIRTUAL: Celebrating America's 250th: "Boston, 1776" with author J.D. Dickey

Mon, Jun 22, 2026 — 7:00pm

Celebrate the 250th anniversary of the signing of the Declaration of Independence with author J. D. Dickey discussing his book, Boston, 1776: A Rogue Tour of Revolution City. Relive the chaos, courage, and color of the American Revolution's capital city while meeting those who led the fight in the nation's War of…

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Venue
Winchester Public Library
Online
Sponsors
Winchester Public Library
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VIRTUAL: Celebrating America's 250th: Common Soldier: Uncommon Hero with historian Bruce E. Mowday

Mon, Jun 29, 2026 — 7:00pm

Historian Bruce E. Mowday will be discussing the common soldier at Valley Forge with a strong New England connection: Connecticut's own Joseph Plum Martin and his diary. We hope you can join us for this fascinating conversation! **Due to limited space, please register only if you can watch the presentation live.

Venue
Winchester Public Library
Online
Sponsors
Winchester Public Library
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Massachusetts Primary Election

Tue, Sep 1, 2026 — 12:00am
Venue
Winchester High School
Sponsors
Winchester Town Clerk
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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 Foundation for Educational Excellence (WFEE)
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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