Events in Cheshire — October 2026 (57 Things to Do)

October 2026 in Cheshire, Connecticut brings 57 live events across the city, led by family (26), art (14), theater (11). 1 events are explicitly listed as free. Here's what's on.

Frequently Asked Questions

What's happening in Cheshire in October 2026?

There are 57 events in Cheshire, Connecticut in October 2026, including Art Exploration with ARTs Studio (Grades K-5) at Cheshire Public Library, Homeschool Hub at Cheshire Public Library, Play and Learn (Ages 0-5 with caregiver) at Cheshire Public Library, Open Art Studio ~Art is for Everyone~ Hosted by Cheshire Art League at Cheshire Public Library. Browse the full October 2026 calendar on VenuNite.

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

Yes — 1 October 2026 event is explicitly listed as free in Cheshire. Confirm current entry details on the event page or organizer source.

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

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

Events in Cheshire — October 2026

All October 2026 Events

Frequently Asked Questions

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Events in Cheshire — October 2026

All October 2026 Events

Art Exploration with ARTs Studio (Grades K-5)

Homeschool Hub

Play and Learn (Ages 0-5 with caregiver)

Open Art Studio ~Art is for Everyone~ Hosted by Cheshire Art League

Manic Presents Music Upstairs with Insomniac/Coma Hole/Sea of Bones

Insomniac

Make Me an Author Creative Writing Club (Grades 3-4)

Time For Twos (Ages 24-36 Months)

STEAM Lab Explorers: Mad Scientist Edition (Grades K-2)

Whimsical Ones (Ages 12-24 Months)

Mahjong Meetup

Leave the Leaves, Save the Stems

Play and Learn (Ages 0-5 with caregiver)

Open Art Studio ~Art is for Everyone~ Hosted by Cheshire Art League

Stories on Saturday (All Ages)

Redscroll Records Presents: Record Fair at Counter Weight

Time For Twos (Ages 24-36 Months)

Explore Your Family Tree (Monthly Group)

Family STEAM Night: Mad Scientist Edition

Winnie-the-Pooh Party (Ages 2-5)

Mahjong Meetup

One Mystery at a Time Group (Online) - Too Old for This

Dodd Drop In (Grades 7-8)

Nutmeg Readers (Grades K-3)

Item Drop-Off for Clothing Swap

Play and Learn (Ages 0-5 with caregiver)

Open Art Studio ~Art is for Everyone~ Hosted by Cheshire Art League

Item Drop-Off for Clothing Swap

Katie Boyle

Manic Presents Comedy Upstairs with Katie Boyle

Fall Clothing Swap

STEAM Lab Jr. Mad Scientist Edition (Ages 3-5)

Make Me an Author Creative Writing Club (Grades 3-4)

Time For Twos (Ages 24-36 Months)

Yarn Garlands (Grades 3-5)

Connecticut 169 Club

Whimsical Ones (Ages 12-24 Months)

Books Over Coffee: How Lucky

Mahjong Meetup

Teen VR (Grades 6-12)

Authors Upstairs with Connecticut Cryptids authors Patrick Scalisi & Valerie Ruby-Omen

Authors Upstairs: Connecticut Cryptids

Books Over Cocoa: How Lucky

Teen Cozy Cafe (Grades 6-12)

Play and Learn (Ages 0-5 with caregiver)

Open Art Studio ~Art is for Everyone~ Hosted by Cheshire Art League

Concert: Hungrytown

STEAM Lab: Mad Scientist Edition (Grades 3-5)

Volunteens Craft

Friends of the Library Meeting

Explore New Worlds: Virtual Reality

Time For Twos (Ages 24-36 Months)

Cupcake Wars (Grades 6-12)

Whimsical Ones (Ages 12-24 Months)

Mahjong Meetup

Happy Halloween Party (Ages 2-5)

Open Art Studio ~Art is for Everyone~ Hosted by Cheshire Art League

Art Exploration with ARTs Studio (Grades K-5)

Art Exploration with ARTs Studio (Grades K-5)

Homeschool Hub

Homeschool Hub

Play and Learn (Ages 0-5 with caregiver)

Play and Learn (Ages 0-5 with caregiver)

Open Art Studio ~Art is for Everyone~ Hosted by Cheshire Art League

Open Art Studio ~Art is for Everyone~ Hosted by Cheshire Art League

Manic Presents Music Upstairs with Insomniac/Coma Hole/Sea of Bones

Manic Presents Music Upstairs with Insomniac/Coma Hole/Sea of Bones

Insomniac

Insomniac

Make Me an Author Creative Writing Club (Grades 3-4)

Make Me an Author Creative Writing Club (Grades 3-4)

Time For Twos (Ages 24-36 Months)

Time For Twos (Ages 24-36 Months)

STEAM Lab Explorers: Mad Scientist Edition (Grades K-2)