Events in Chesapeake — October 2026 (34 Things to Do)

October 2026 in Chesapeake, Virginia brings 34 live events across the city, led by community (10), art (7), food & drink (6). 3 events are explicitly listed as free. Here's what's on.

Frequently Asked Questions

What's happening in Chesapeake in October 2026?

There are 34 events in Chesapeake, Virginia in October 2026, including Chesapeake Rotary Foundation First Citizen Banquet at Chesapeake Conference Center, Self Defense and Awareness Class at Complementary Sound Therapy and Wellness Center (10:00 AM), "Intro to Real Estate Investing" Lunch & Learn at The Garage Brewery (12:00 PM), Dream Her Future at Greenbrier Country Club (5:30 PM). Browse the full October 2026 calendar on VenuNite.

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

Yes — 3 October 2026 events are explicitly listed as free in Chesapeake. Confirm current entry details on the event page or organizer source.

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

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

Events in Chesapeake — October 2026

All October 2026 Events

Frequently Asked Questions

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Events in Chesapeake — October 2026

All October 2026 Events

Chesapeake Rotary Foundation First Citizen Banquet

Self Defense and Awareness Class

"Intro to Real Estate Investing" Lunch & Learn

Dream Her Future

Tai Chi, Qi Gong, and Kung Fu

Sunday Soiree Gospel Sing-A-Long

Trust Your Journey Meditation

Southern Flair Open Mic Tuesdays

Oath Law Educational Workshop

Chesapeake Rotary

Oath Law Educational Workshop

Little Mania - Midget Wresting All Stars

College & Career Readiness Night

AMFM Healthcare

Rosè & Radiance Wellness Fair

Rose & Radiance Celebration – Black Tie Gala

In Full Bloom: A Floral & Wine Experience

Creative Spark Workshops- October

Chesapeake Rotary

Monthly Themed Live Trivia Nights at Bubba's 33 - Chesapeake Square

A. Smith Bowman Dinner with Master Distiller David Bock

Craft & Chat October 16th:(CC3): Bedazzling Night

Reins Of Impact

Love Songs on Sunday's Fall Wellness Festival

Halloween costume paint n sip

VDVS – Veterans Benefits Fair

Embracing Hope Relationship Adult Prom & Talent Show

“Crowned With A Purpose” Women's Brunch

Miss Cultural 2026: The Beauty Within

Halloween Cookie Decorating Class @ Studly Brewing

Joe Smith 2nd Annual Fall Classic Golf Fundraiser

Chesapeake Rotary

RVC Networking Social

Meet Me Outside Halloween Day Party

Chesapeake Rotary Foundation First Citizen Banquet

Chesapeake Rotary Foundation First Citizen Banquet

Self Defense and Awareness Class

Self Defense and Awareness Class

"Intro to Real Estate Investing" Lunch & Learn

"Intro to Real Estate Investing" Lunch & Learn

Dream Her Future

Dream Her Future

Tai Chi, Qi Gong, and Kung Fu

Tai Chi, Qi Gong, and Kung Fu

Sunday Soiree Gospel Sing-A-Long

Sunday Soiree Gospel Sing-A-Long

Trust Your Journey Meditation

Trust Your Journey Meditation

Southern Flair Open Mic Tuesdays

Southern Flair Open Mic Tuesdays

Oath Law Educational Workshop

Oath Law Educational Workshop

Chesapeake Rotary

Chesapeake Rotary

Oath Law Educational Workshop

Oath Law Educational Workshop

Little Mania - Midget Wresting All Stars

Little Mania - Midget Wresting All Stars

College & Career Readiness Night

College & Career Readiness Night

AMFM Healthcare

AMFM Healthcare

Rosè & Radiance Wellness Fair

Rosè & Radiance Wellness Fair

Rose & Radiance Celebration – Black Tie Gala

Rose & Radiance Celebration – Black Tie Gala

In Full Bloom: A Floral & Wine Experience

In Full Bloom: A Floral & Wine Experience

Creative Spark Workshops- October

Creative Spark Workshops- October

Chesapeake Rotary

Chesapeake Rotary

Monthly Themed Live Trivia Nights at Bubba's 33 - Chesapeake Square

Monthly Themed Live Trivia Nights at Bubba's 33 - Chesapeake Square