Events in the Cayman Islands

Celebrating the culinary capital of the Caribbean!

Spotlight on Tour

Harquail Theatre, F.J. Harquail Cultural Centre, 17 Harquail Drive, George Town

7:00pm - 9:00pm

Spotlight returns with an evening of musical entertainment at the Harquail Theatre.

Wed 28 Oct

Survivors’ Voices Panel Discussion

By: Cayman Crisis Centre

6:00pm - 7:30pm

Hear four survivors share their stories of domestic abuse, resilience and the need for change.

55 Market Street, Camana Bay, George Town

Sat 31 Oct

Pirates Week 2026 Celebrations

By: Cayman Islands Government

11:00am - 11:00pm

Celebrate Pirates Week with landings, competitions, food, fireworks and family fun.

George Town

Sat 31 Oct

Inclusive Halloween Family Festival

By: Autism Acceptance

10:00am - 7:00pm

A free inclusive Halloween festival with family activities, food and fun.

Autism Acceptance, 13 Melody Lane, George Town

Sat 07 Nov

LIFE Literacy Conference 2026

By: Literacy Is For Everyone (LIFE)

9:00am - 4:15pm

A free conference exploring shared responsibility for early childhood success.

Kimpton Seafire Resort + Spa, West Bay

Tue 10 Nov

Cayman Youth Choir - “One Moment in Time”

By: Cayman Arts Festival

6:00pm - 7:00pm

Cayman Youth Choir takes audiences on a joyful musical journey through time.

John Gray High School Performance Hall, John Gray High School, 135 Olympic Way, George Town

Tue 17 Nov

Bedi Walker Boarding School Fair

By: Bedi Walker

6:00pm - 8:00pm

Meet representatives from 20+ North American boarding schools in Grand Cayman.

Grand Cayman Marriott Resort, 389 West Bay Road, Seven Mile Beach

Fri 20 Nov

Ladies Golf for Good

By: Sentient Charitable Foundation

From 8:30am.

A ladies' nine-hole golf tournament raising funds for Cayman Islands Crisis Centre.

The Ritz-Carlton Golf Club, 1066 West Bay Road, Seven Mile Beach

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Tue 13 Oct

Cayman Restaurant Month 2026

Celebrating the culinary capital of the Caribbean!

Tue 13 Oct

Community Chess, Sunset House

By: Cayman Chess Club

From 5.30pm

Join the Cayman Chess Club for a complimentary chess class and open challenges weekly. Anyone can learn, play and enjoy chess; even complete beginners.

Sunset House

Wed 14 Oct

Cayman Restaurant Month 2026

Celebrating the culinary capital of the Caribbean!

By: Cayman Islands Sailing Club

Wed 14 Oct

Wednesday Night Hartley Club Sailing/Racing, CISC

4:30pm - 6:30pm

CISC would like to welcome sailors to join us for Wednesday night club sailing/racing.

Cayman Islands Sailing Club, Spinnaker Road, Red Bay

Thu 15 Oct

Cayman Restaurant Month 2026

Celebrating the culinary capital of the Caribbean!

Thu 15 Oct

To Kill A Mockingbird

The Prospect Playhouse, 223B Shamrock Road, Prospect

A powerful stage adaptation exploring prejudice, compassion and moral courage.

Cayman Restaurant Month 2026

Celebrating the culinary capital of the Caribbean!

Spotlight on Tour

Harquail Theatre, F.J. Harquail Cultural Centre, 17 Harquail Drive, George Town

7:00pm - 9:00pm

Spotlight returns with an evening of musical entertainment at the Harquail Theatre.

To Kill A Mockingbird

The Prospect Playhouse, 223B Shamrock Road, Prospect

A powerful stage adaptation exploring prejudice, compassion and moral courage.

Cayman Restaurant Month 2026

Celebrating the culinary capital of the Caribbean!

By: Cayman Islands Government

Halloween Movie Special: Spellbound

11:00am - 1:00pm

A free family Halloween screening of Spellbound with snacks at local libraries.

East End Public Library, West Bay Public Library, North Side Public Library, George Town Public

High Tea & Bubbles: Navigating Perimenopause & Menopause with Clarity

Union Grill, 18 Market Street, Camana Bay

2:00pm - 4:00pm

Dr Mubeen discusses perimenopause, menopause and women's hormonal health.

By: Cayman Islands Youth Development Consortium

Planning for Youth Success Conference

9:00am - 3:00pm

Youth and adults come together to turn ideas into action for Cayman’s young people.

Central Scranton Park, off Shedden Road, George Town

Spotlight on Tour

Harquail Theatre, F.J. Harquail Cultural Centre, 17 Harquail Drive, George Town

7:00pm - 9:00pm

Spotlight returns with an evening of musical entertainment at the Harquail Theatre.

To Kill A Mockingbird

The Prospect Playhouse, 223B Shamrock Road, Prospect

A powerful stage adaptation exploring prejudice, compassion and moral courage.

By: Culture at the Cinema

Kids Club at the Cinema, Grand Cayman

10:00am - 11:30am

Family friendly movies are shown weekly at the cinema.

Camana Bay Cinema

By: Cayman Islands National Museum

Free Admission for Residents, Cayman Islands National Museum

Residents can enjoy free entry to the National Museum every Saturday.

Cayman Islands National Museum, 3 Harbour Drive at Shedden Road, George Town

Sun 18 Oct

Cayman Restaurant Month 2026

Celebrating the culinary capital of the Caribbean!

Sun 18 Oct

Spotlight on Tour

Harquail Theatre, F.J. Harquail Cultural Centre, 17 Harquail Drive, George Town

5:00pm - 7:00pm

Spotlight returns with an evening of musical entertainment at the Harquail Theatre.

Sun 18 Oct

To Kill A Mockingbird

The Prospect Playhouse, 223B Shamrock Road, Prospect

A powerful stage adaptation exploring prejudice, compassion and moral courage.

Mon 19 Oct

Cayman Restaurant Month 2026

Celebrating the culinary capital of the Caribbean!

Tue 20 Oct

Cayman Restaurant Month 2026

Celebrating the culinary capital of the Caribbean!

Tue 20 Oct

Community Chess, Sunset House

By: Cayman Chess Club

From 5.30pm

Join the Cayman Chess Club for a complimentary chess class and open challenges weekly. Anyone can learn, play and enjoy chess; even complete beginners.

Sunset House

Wed 21 Oct

Cayman Restaurant Month 2026

Celebrating the culinary capital of the Caribbean!