Events happening in Oakville.

Thursday, October 15th

8:00PM – 10:00PM

Sing Pitch Perfect with Deke Sharon & Splush

Sing Pitch Perfect with Deke Sharon & Splüsh 🎤 Deke Sharon, Music Director for the three Pitch Perfect films, will lead attendees in learning and singing "Since U Been Gone" entirely a cappella. Sheet music will be provided for all participants. Splüsh, the SING! Canadian A Cappella 2025 double champions, will perform. Deke will also share behind-the-scenes stories from the movie-making process. Open to all ages and singing levels — non-singers are welcome.

Oakville Centre — AEG Liebherr Auditorium

Friday, October 16th

7:00PM

Haunted Happenings: Candlelight Tour

Step into the shadows this October… if you dare. Join the Oakville Museum for a unique Halloween experience where history and Halloween come together inside the beautifully preserved Erchless Estate. Wander from room to room as your guide reveals the curious origins of Halloween traditions, from eerie Victorian mourning customs and ghostly superstitions to fortune telling, jack-o’-lanterns, witches, cats and bats, and of course tricks as well as treats. Along the way, take part in a themed scavenger hunt as you search for hidden clues and surprises throughout the historic home then solve the riddle and get a special Halloween treat to take home as part of your evening adventure. Packed with history, mystery, and sprinkled with just the right amount of seasonal magic, this one-of-a-kind experience is perfect for curious minds of all ages who want a Halloween outing with a playful twist. This spirited tour is sure to leave you enchanted. History has never been so haunting!

Oakville Centre — Oakville Museum

Saturday, October 17th

10:00AM – 2:00PM

Family Saturdays | Pumpkin Carving

Oakville Galleries is hosting a Halloween day of creative activities for all ages. Attendees are invited to bring their own pumpkin to carve — no experience needed. A Halloween-themed craft station is available for children to make treats to take home. Classic Halloween family films will play throughout the day, and hot chocolate and sweet treats will be provided. For more information, contact Oakville Galleries at [email protected] or 905-844-4402.

Oakville Galleries in Gairloch Gardens · $10

Sunday, October 18th

12:00AM – 12:00AM

Wiggle Waggle Walk

Wiggle Waggle Walk 🐾 The Humane Society of Oakville, Milton & Halton (HSOMH) hosts this community fundraising walk, presented by Royal Canin. The event brings together supporters, families, alumni, and animal lovers to raise funds for HSOMH's mission of supporting people and their pets, helping animals, and promoting animal welfare in the region. River Oaks Community Centre, 2400 Sixth Line, Oakville.

River Oaks Community Centre, Room A

Saturday, October 24th

10:00AM

Haunted Happenings: Tricks, Treats and Traditions

Gather the whole family for some charming old-fashioned Halloween fun at the Oakville Museum! Young visitors can follow their very own Halloween Passport as it guides them throughout the historic estate and grounds to take part in festive activities, crafts, outdoor games, and seasonal surprises. Travel through centuries of Halloween traditions on a delightfully spirited guided tour of Erchless Estate. Enjoy a bit of creative mischief with a festive Halloween craft. Settle in with complimentary popcorn and warm apple cider as you enjoy a delightful selection of classic silent movie shorts and vintage Halloween cartoons at the Coach House. Wander over to our enchanted gingerbread cottage to collect a sweet treat and have your fortune told by our resident friendly witch. Costumes are highly encouraged, so come dressed as your favourite ghost, goblin, or storybook character and join in the festive spirit. It’s a magical mix of nostalgic entertainment, historic charm, and family-friendly Halloween memories sure to delight visitors of every age. *Artwork by Laetitia Wong

Oakville Centre — Oakville Museum · Free

Saturday, October 24th

10:00AM – 2:00PM

Halloween Spooktacular

🎃 Children enjoy an open-air, outdoor Halloween Hunt. Outdoors by Entrance 3, off Leighland Ave, by Stack restaurant. 🎃 Families take their individual turn exploring a “not-so-spooky” haunted walk-through for their own prepackaged treat bag. 🧡 Tim Hortons on site to join the Halloween fun. Reservations and prepayment required. Children $10+hst Adults free To reserve your lineup window time, email [email protected] , DM @duranplaceforkids on Instagram, or call 905-609-2223.

Oakville Place · $10

Sunday, October 25th

10:00AM – 2:00PM

Haunts & Harvest at the Bronte Farmers’ Market

Join us for Haunts & Harvest, the final Bronte Farmers’ Market of the year – with a fun Halloween twist! Explore 40+ local vendors, enjoy live music and dancing, and soak up the festive fall atmosphere. With surprises around every corner, there’s plenty to discover, taste, and enjoy. Come celebrate the season and close out another great market year with us!

Bronte Market Square, 2445 Lakeshore Road West

Sunday, October 25th

1:00PM – 3:00PM

The Velveteen Rabbit

The Velveteen Rabbit is a musical adaptation by Mya Leworthy, Naomi Jijina, and Lucy Ellis. On Christmas Eve, a young boy sneaks downstairs to search for a toy rocket among the presents. His grandmother discovers him and agrees to let him stay up late — but only if he listens to her story about a toy called the Velveteen Rabbit. Performance begins at 1:00 p.m. at Oakville Centre for the Performing Arts, 130 Navy Street, Oakville.

Oakville Centre — AEG Liebherr Auditorium

Saturday, October 31st

10:00AM – 12:00PM

Tiny Tots 2026

Tiny Tots 2026 Location: Downtown Oakville Time: Starts 10:00 a.m. Tiny Tots is back! Join Downtown Oakville on October 31st for a fun-filled morning of trick-or-treating! Bring your little ones in costume and visit participating businesses along Lakeshore and nearby streets for sweet treats and Halloween Fun. For more information, contact [email protected] .

Downtown Oakville

Saturday, October 31st

1:00PM

Tails & Treats

No tricks, just treats for your four-legged friends! Dress them up and join us for treats, prizes and Halloween fun. For more information, contact [email protected] .

Downtown Oakville

Sunday, November 1st

12:00PM – 9:00PM

SWASTHYAM DIWALI

OAKVILLE’S VERY OWN FREE ANNUAL DIWALI CELEBRATION IS BACK! Get ready for a dazzling celebration of light, culture, community and joy!

St. Volodymyr Cultural Centre - SVCC · Free

Fri, Nov 20 – Thu, Dec 24

Santa Photos Book Now Special Offer

Join us for photos with Santa, where little smiles, festive outfits, and merry memories come to life at Oakville Place. Appointments fill up faster than Santa’s sleigh on Christmas Eve, so don’t wait.RESERVE NOW Photos with Santa November 20 – December 24$10 off Elite package. Enter code SANTA10 at checkout. Only valid for visits on or before 12/11/26. Expires on 11/1/26. Not valid with any other offers.

Centre Court

Sat, Nov 28 – Sun, Nov 29

G.F. Handel's MESSIAH

The most wonderful event of the season! Start the holidays off right with a performance of Handel's Messiah.

St Andrew's Catholic Church

Saturday, December 5th

1:00PM

Lady Next Door

Two neighbours share a common courtyard — Huguette, exuberant and free-spirited, and Vana, orderly and organized. Their clashing lifestyles create constant friction: Huguette hangs laundry to loud music, sets up a tent for backyard camping, and practices acrobatic bike tricks, while Vana is most bothered by Huguette's perpetually overflowing garbage cans. Through the chaos, the neighbours gradually learn to communicate and understand each other better. A glimmer of friendship emerges as they discover they may not be so different after all. This female clown duo delivers physical comedy and heart — expect to laugh until you cry.

Oakville Centre — AEG Liebherr Auditorium

Sunday, December 13th

1:30PM

Family Holiday Concert

Orchestral, Concert, Christmas, Classical Fill your heart with joy and cheer, and the spirit of the holidays in an exciting one-hour concert for the entire family.

Oakville Centre — AEG Liebherr Auditorium

Sat, Dec 19 – Sun, Dec 27

A Wicked Christmas Carol - A Holiday Pantomime

Christmas, Musical Theatre Bah, munchbug! Elphabeneezer Scrooge, the holiday-hating Wicked Witch of the West is hidden away in her castle trying to ignore Christmas but, on the other side of the yellow brick road, the secretly evil Wizard of Ozville is plotting to get rid of her. FOR GOOD. Glinda is sure she can save her old friend from the nasty Wizard’s plans - three spirits and a little of bit of time travel should do the trick. Oh, and you! The good guys are going to need your magical powers, cheers, and boos if they’re going to save the day. So come join us for a hilarious mash-up of classics - and get your tickets soon because as Glinda would say… Popular! We’re gonna be popular!

Oakville Centre — AEG Liebherr Auditorium

Thursday, December 31st

1:00PM

Grand Illusion: Edllusion

The Grand Illusion Show is a 90-minute live theatre experience blending grand illusions, mind-reading, comedy, and high-energy theatrical showmanship. A dynamic cast of professional assistants and dancers performs stunning visual illusions, shocking reveals, and crowd-pleasing comedy designed to engage audiences throughout. The production is suitable for all ages and works well for family outings, friend groups, or group nights out.

Oakville Centre — AEG Liebherr Auditorium

Friday, January 29th

7:00PM

No Excuses, No Limits

No Excuses, No Limits 🎤 ILL-Abilities is an international award-winning breakdance crew comprising Bboys with disabilities. The ensemble has performed in over 25 countries and reached more than 1 million audiences globally. This production takes audiences on a journey through each dancer's personal story, combining dance, music, and audience interaction to explore the limitless possibilities within any person. The show sold out 10 sessions at Kennedy Center in Washington D.C., USA. The crew's name plays on the word "ill," a term from hip-hop culture used to describe something positive and exceptional. ILL-Abilities uses dance, optimistic attitudes, and personal narratives to inspire and spread positive thinking.

Oakville Centre — AEG Liebherr Auditorium