TNAP Highlights: What’s new in Singapore May 2026

May brings a vibrant mix of celebrations and activities to Singapore! Kick off the month with Labour Day, then honour moms with special Mother’s Day treats and not forgetting the June school holidays.

Cultural highlights include Vesak Day observances and Hari Raya Haji. From cultural traditions to maritime adventures, discover the best ways to enjoy this action-packed month!

⇒ Related Read: Mother’s Day Gifts Every Mum Will Love

1. Sail the Currents that Shape Us at Singapore HeritageFest 2026

Through islandwide cultural performances, scenic water and land tours, guided trails, workshops and exhibitions, SHF 2026 reveals Singapore’s deep connection to the sea and the vibrant communities that made us a global maritime hub.

This year, festival-goers can embark on a captivating journey through Singapore’s maritime past, exploring how trade, migration, beliefs and practices, and naval history have shaped the island we know today.

📅 1 to 24 May 2026
📍 Islandwide

For more information, visit Singapore HeritageFest (SHF) 2026.

*******************************

2. Five Footway Festival 五脚基节 5th Edition at Chinatown Singapore

Five Footway Festival, also known as 五脚基节, transforms Smith Street into a vibrant showcase of living heritage, where culture, community and street life come together in the heart of Chinatown Singapore.

Held at the rejuvenated Cultural Heart @ Smith Street Chinatown Singapore, the Festival invites both locals and tourists to immerse themselves in a line-up of traditional performances, hands-on workshops and nostalgic street experiences.

📅 2 to 10 May 2026 (Sat & Sun performances only)
📍 Chinatown Singapore

For more information, visit Five Footway Festival 2026.

*******************************

3. Charlie and the Chocolate Factory Singapore: A Magical Family Musical Experience

Based on Roald Dahl’s globally beloved novel, CHARLIE AND THE CHOCOLATE FACTORY follows young Charlie Bucket’s golden ticket adventure into the mysterious and magical world of Willy Wonka’s chocolate factory. From chocolate rivers to nut-sorting squirrels and mischievous Oompa-Loompas, the musical dazzles with eye-popping visuals, larger-than-life characters, immersive delight for audiences, and toe-tapping music.

The musical features iconic songs from the classic 1971 film, including “Pure Imagination,” “The Candy Man,” and “I’ve Got a Golden Ticket,” along with original music by Grammy® and Tony Award® winners Marc Shaiman and Scott Wittman (Hairspray, Mary Poppins Returns).

📅 from 19 May 2026
📍 Sands Theatre, Marina Bay Sands

For more information, visit Charlie and the Chocolate Factory Singapore.

*******************************

4. Singapore International Festival of Arts (SIFA) 2026

Courtesy of Arts House Group

Revel in the arts this May through play! The Singapore International Festival of Arts (SIFA), Singapore’s pinnacle annual performing arts festival organised by Arts House Group and commissioned by the National Arts Council, returns with a vibrant constellation of performances, installations and encounters – from epic productions to engaging, participatory works.

Led by the call-to-action “Let’s Play!”, SIFA 2026 invites audiences to explore, experiment, engage and be inspired by the arts.

📅 15 to 30 May 2026
📍 Various locations in Singapore

For more information, visit Singapore International Festival of Arts (SIFA) 2026.

*******************************

5. PolandSHIOK!

📅 16 May 2026
🕙 6pm – 7pm
📍 Shaw Foundation Symphony Stage

For more information, visit PolandSHIOK!.

*******************************

Note: All details are correct as at the time of publishing. While every effort has been made to ensure the accuracy and completeness of the information, no guarantee is given nor responsibility is taken for errors or omissions in the compilation. Readers are advised to check with the respective event organisers for the most updated schedules, venues and details.

💐👩‍👧‍👦 MOTHER’S DAY 2026 👩‍👧‍👦💐

Mother’s Day is just around the corner! Treat Mum to a well-deserved celebration – explore our curated list of Mother’s Day dining spots, thoughtful Mother’s Day gifts, and beautiful Mother’s day cakes to make her day extra special.

🎭🎪 JUNE SCHOOL HOLIDAY 2026 🎪🎭

Welcome to the June school holidays! Make the most of the break with your little ones – explore our curated list of fun, engaging, and family-friendly activities happening across Singapore during the June School Holidays in Singapore 2026.