Community

Public meetings, parades, and other community-oriented activities and events of general interest

14th Annual Massachusetts Walking Tour

At 3 pm: Group Hike on the Tri-Community Trail, leaving from and returning to Winchester Unitarian Society parking lot. This loop hike is approximately 4.4 miles in total along the beautiful shores of the Mystic Lakes and through the Brooks Estate. Mostly flat walking on pavement or dirt path along lakes, hiking in woods and some elevation changes in Brooks Estate. Options to shorten the hike by joining or leaving from Upper Mystic Lake Dam parking lot. 

At 6 pm: concert at the Winchester Unitarian Society, sponsored by the Blackstone Valley Music & Performing Arts Collaborative. Refreshments

2025 Civic Leadership Award Ceremony

The LWV Steering Committee is proud and excited to announce that M. Joyce Westner will be the recipient of the 2025 Civic Leadership Award. Please join the League on Thursday, September 18, 2025 for the 2025 Civic Leadership Award Ceremony in the Town Hall Auditorium.

Joyce has provided a tremendous service to our community, bringing idealism balanced with professionalism to shape public discourse in a civil fashion. Joyce effectively engages a wide range of people, often while tackling some of the most challenging community concerns. Most recently, Joyce responded to the clear need for

2025 En Ka Fair

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.

Buy tickets online (enkasociety.org) or use the link below until May 14.
https://form.jotform.com/250806537696165

Buy tickets onsite starting May 15 (12-6pm), and during Fair's hours.

This year the Fair's hours are:
Friday, May 16, 4-10pm
Saturday, May 17, 10am-9pm (Parade is at 9:15am)

Sponsors

2025 Holiday Faire at Crawford Memorial UMC

On Saturday, Nov. 8, 2025, Crawford Memorial United Methodist Church, 34 Dix St., will hold its annual Holiday Faire, from 8:30 a.m. to 2 p.m. Come for Crawford's famous apple pies and fabulous cookie bar; the Christmas room with a splendid array of lovely holiday decorations and other exciting items not found in local stores; beautifully handcrafted goods and gift baskets; delightful and unique ideas for everyone; fun vintage jewelry; scrumptious baked goods; delicious breakfasts and lunches at the snack bar, and the white elephant sale including books, housewares, toys, the holiday room, and

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A Night With Koshari Mama

Koshari Mama presents vegan Egyptian delights. From the rich spices to the traditional dishes, this buffet offers a culinary journey through the heart of Egypt, all in a fun and welcoming atmosphere. To make the evening even more special, we’ll have a live belly dancer performance between courses, adding an exciting cultural experience to the night! Basic cost: $84; lower and higher tiered prices available.

AANHPI Celebration!

Join us at Winchester High School (80 Skillings Road) on Tuesday, May 20, from 5:30 – 7:30 for a family-friendly Asian American Native Hawaiian Pacific Islander celebration! There will be entertainment, educational activities, advocacy, food and more. This event is free and open to everyone. We hope you’ll join the fun!

Anastasia Sierra Artist Reception

Join us at WinCam Gallery on July 24th, 5.30pm - 7pm, for an artist reception with Anastasia Sierra to celebrate her solo exhibition, Bittersweet. Sierra's intimate project explores the emotional complexity of motherhood through colorful staged portrait photogrphy.

About Bittersweet -

Bittersweet is an ongoing body of work about the conflicting emotions of motherhood, where love and joy live next to the feelings of frustration, guilt and exhaustion.

I collaborate with my young son to recreate moments of tenderness and tension. Together, we make a colorful and mysterious world of

Annual Outdoor Living and Garden Tour

Be inspired by the green thumbs of your neighbors while visiting 7 uniquely blooming backyards scattered throughout town.

List of participating locations will be provided to all ticket holders in advance of the tour.

An unique option to have lunch in one of the gardens will be an additional $15. Lunch will be served from 12-2 and the location of the lunch will be sent to you once the ticket has been purchased.
All proceeds support the Town Beautification Fund managed by the Chamber, supporting projects that keep Winchester beautiful year round.
Thank you to our sponsor: Jessica

Art in August Opening Reception

The Winchester Cultural Council and the Winchester Artists Network invite you to a gala reception to celebrate the opening of Art in August 2025.

Come meet the artists who are exhibiting throughout August in locations throughout the town, the merchants who generously donate space in their shops and windows, state and town leaders, Winchester Cultural Council members and local grant recipients, and others from our community.

Wine and light appetizers served. All are invited, free admission.