Events in Winchester — October 2026 (38 Things to Do)

October 2026 in Winchester, Massachusetts brings 38 live events across the city, led by community (24), art (3), wellness (3). Here's what's on.

Frequently Asked Questions

What's happening in Winchester in October 2026?

There are 38 events in Winchester, Massachusetts in October 2026, including Winchester Housing Authority at Winchester Town Hall, Walls, Rock & Rum: Colonial History of the Middlesex Fells at Winchester Town Hall, CONSERVATION COMMISSION at Winchester Town Hall, Conservation Commission Legal Notice- 3 Cutting St at Winchester Town Hall. Browse the full October 2026 calendar on VenuNite.

Are there free things to do in Winchester in October 2026?

No October 2026 events in Winchester are currently marked free. Events with an unknown price are not counted as free.

How do I find events in Winchester for a specific date in October 2026?

VenuNite lists every upcoming event in Winchester, Massachusetts with date filters. Use the date picker on this page to narrow October 2026 down to a single day or weekend.

Events in Winchester — October 2026

All October 2026 Events

Frequently Asked Questions

Browse Live Events by State

Events in Winchester — October 2026

All October 2026 Events

Winchester Housing Authority

Walls, Rock & Rum: Colonial History of the Middlesex Fells

Conservation Commission

Conservation Commission Legal Notice- 3 Cutting St

Winchester Council on Aging

Smart Solutions for Independence at Home

Winchester Cultural Council

Winchester Farmers Market — Saturday

Winchester Farmers Market

Early Voting in Person

Jazz Blessing of the Animals

Portfolio Prep: Photography for College & AP with David Oxton

Personal Mastery Workgroup

Early Voting in Person

Bird and Nature Walk around Long Pond, Winchester

Early Voting in Person

Mahjong & Mingle Open Play Night

An Evening with Gretchen Powell Fox

Early Voting in Person

Autumn at Long Pond

Early Voting in Person

Early Voting in Person

Dr. Feverdream's Haunted House and Rainforest Adventure

Voter Registration Deadline for State Election

Winchester Farmers Market — Saturday

Winchester Farmers Market

Dr. Feverdream's Haunted House and Rainforest Adventure

Portfolio Prep: Photography for College & AP with David Oxton

Ballot Test - Voting Machines for State Election

Early Voting in Person

ACOTAR 6 Midnight Release Party!

Vote by Mail Application Deadline - State Election

Early Voting in Person

Early Voting in Person

Early Voting in Person

Early Voting in Person

Autumn Walk at Wright-Locke Farm in Winchester

Winchester Farmers Market

Winchester Housing Authority

Winchester Housing Authority

Walls, Rock & Rum: Colonial History of the Middlesex Fells

Walls, Rock & Rum: Colonial History of the Middlesex Fells

Conservation Commission

Conservation Commission

Conservation Commission Legal Notice- 3 Cutting St

Conservation Commission Legal Notice- 3 Cutting St

Winchester Council on Aging

Winchester Council on Aging

Smart Solutions for Independence at Home

Smart Solutions for Independence at Home

Winchester Cultural Council

Winchester Cultural Council

Winchester Farmers Market — Saturday

Winchester Farmers Market — Saturday

Winchester Farmers Market

Winchester Farmers Market

Early Voting in Person

Early Voting in Person

Jazz Blessing of the Animals

Jazz Blessing of the Animals

Portfolio Prep: Photography for College & AP with David Oxton

Portfolio Prep: Photography for College & AP with David Oxton

Personal Mastery Workgroup

Personal Mastery Workgroup

Early Voting in Person

Early Voting in Person

Bird and Nature Walk around Long Pond, Winchester

Bird and Nature Walk around Long Pond, Winchester

Early Voting in Person

Early Voting in Person

Mahjong & Mingle Open Play Night

Mahjong & Mingle Open Play Night

An Evening with Gretchen Powell Fox

An Evening with Gretchen Powell Fox