Events happening in Oakville.

Sat, Dec 5 – Sun, Dec 6

SV Christmas Market 2026

80 incredible local and regional vendors. One of a kind gifts! Delicious food! Free Admission! Free admission! The first 50 visitors will each receive one entry in our draw for special prizes! Shop from 80 incredible local and regional vendors offering everything from handmade crafts and unique art to gourmet treats and festive decor. Find that perfect, one-of-a-kind gift! Visit Fireside Cafe on site and enjoy delicious food! • Parking: Free parking is available on-site at St. Volodymyr Event Centre. • Public Transit: Accessible via local transit routes (Oakville Transit). • Accessibility: The venue is fully wheelchair and stroller accessible. • Family Friendly: All ages are welcome!

St. Volodymyr Event Centre · Free

Saturday, December 5th

10:00AM – 3:00PM

CHRISTMAS MARKETPLACE

St. Joseph's Annual Christmas Marketplace 🎄 St. Joseph's Ukrainian Catholic Church invites parishioners, neighbours, and friends to its Annual Christmas Marketplace on Saturday, December 5, 2026, from 10:00 AM to 3:00 PM at the St. Joseph's Banquet & Conference Centre, 300 River Oaks Boulevard East, Oakville. The festive ballroom features over 40 local artists, crafters, and small businesses offering handmade holiday gifts. Traditional homemade Ukrainian lunch is available, along with a baked goods table featuring Ukrainian treats and sweets. Admission is free. All are welcome.

300 River Oaks Blvd E · Free

Sat, Dec 5 – Sun, Dec 6

The Atelier: Craft Fair

Oakville Galleries is hosting The Atelier: Craft Fair, a holiday market featuring local and regional crafts. Friday, December 5: 11:00 a.m. – 6:00 p.m. Saturday, December 6: 11:00 a.m. – 4:00 p.m. Oakville Galleries, Gairloch Gardens, 1306 Lakeshore Road East, Oakville. For more information, contact [email protected] or call 905-844-4402.

Oakville Galleries in Gairloch Gardens⁠ · Free

Saturday, December 5th

1:00PM – 6:00PM

Christmas Tour and Treat

Step back in time at Erchless Estate, beautifully decorated for an 1800s Christmas. Visitors will see fanciful ornaments, adorned trees, vintage fashions, and antique toys. Tours conclude with a festive treat and a hot beverage. For more information, contact the Oakville Museum at [email protected] or (905) 338-4400.

Oakville Museum

Saturday, December 5th

1:00PM – 6:00PM

Lady Next Door

Two neighbours share a common courtyard — and they couldn't be more different. Vana is orderly and organized; Huguette is exuberant and messy, delighting in loud music while hanging laundry, camping in her yard, and practicing acrobatic bike stunts. What troubles Vana most are Huguette's perpetually overflowing garbage cans. Through conflict and conversation, the neighbours begin to understand each other, and an unexpected friendship blooms. A female clown duo brings this story to life with physical comedy and heart.

Oakville Centre — AEG Liebherr Auditorium · $20

Sat, Dec 5 – Sun, Dec 20

Downtown Oakville’s Hometown Holiday Cheer

Family-friendly activities include holiday carollers, a photobooth, horse-drawn carriage rides, Santa, and hot chocolate. For more information, contact [email protected].

Downtown Oakville

Sunday, December 6th

11:00AM – 3:00PM

A Victorian Christmas Tea

Join us for a Victorian Christmas Tea hearthside in the cosy fireplace room of The Cottages, in the heart of Old Oakville. Enjoy the ambience of this historical setting, festively wreathed with boughs and candles, while costumed attendants serve you tea at small tables, beautifully decorated with white tablecloths and lovely vintage china.

Oakville Historical Society

Sunday, December 6th

5:00PM – 9:00PM

West End Jazz Presents: Season Finale Gala Night

The West End Jazz series presents an evening of dinner theatre featuring the Swing Shift big band, one of Canada's best jazz orchestras, alongside four accomplished vocalists. Attendees may choose to enjoy dinner, attend the show only, or both. Doors open at 4:00 PM, dinner is served at 5:00 PM, and the show begins at 6:00 PM.

Oakville Conference Centre

Wed, Dec 9 – Fri, Dec 18

The Addams Family

Normal is overrated. Theatre Sheridan presents THE ADDAMS FAMILY, a hauntingly hilarious exploration of family, secrets, and individuality. In one fateful night, relationships are tested and truths are disclosed as the Addams family confronts their worst nightmare: change. The story unfolds in the kooky world of the living, dead, and somewhere in between, celebrating what it means to be an Addams. For more information, contact [email protected] or call (905) 815-4049.

Macdonald Heaslip Hall - Sheridan Trafalgar Campus

Wednesday, December 9th

10:00AM – 11:30AM

Halton Memory Cafe – Oakville

The Halton Memory Café is a welcoming social gathering for people living with dementia and their care partners. Each session offers a relaxed opportunity to connect with others, enjoy meaningful conversation, participate in light activities, and spend time in a supportive community setting. The Memory Café is friendly and inclusive — not a clinical program or formal education session. It is designed to be comfortable for both the person living with dementia and their care partner. Registration is free. Space may be limited, and advance registration is requested to help organizers plan for seating, refreshments, and activities.

Glen Abbey United Church · Free

Thursday, December 10th

6:30PM – 8:30PM

Winter Wonderland Paint and Sip

Holiday Paint and Sip 🎨 Oakville Galleries is hosting a festive evening of painting for adults. Led by instructor Emma Loiselle, this one-night workshop invites participants to explore winter's colours and atmosphere in a relaxed and welcoming setting. Attendees will be guided through techniques to create a winter-inspired scene, drawing on seasonal imagery such as snowy landscapes, glowing evening skies, and the subtle warmth and light of the holidays. The focus is on layering colour, texture, and light. No prior experience is necessary. Wine and light refreshments will be served. For more information, contact Oakville Galleries at [email protected] or call 905-844-4402.

Oakville Galleries in Gairloch Gardens

Fri, Dec 11 – Sat, Dec 12

Classic Albums Live: The White Album

Classic Albums Live recreates The Beatles' White Album with exacting precision. Founder Craig Martin explains the group's philosophy: "We don't dress up or wear costumes. All our energy is put into the music. We want the performance to sound exactly like the album. These albums are sacred to people. We deliver exactly what we promote — 'note for note, cut for cut' accuracy." Act One is a flawless, note-for-note recreation of the album, bringing every detail to life. Act Two shifts to celebrate the band's legacy with their greatest hits, including "Back In the U.S.S.R.", "While My Guitar Gently Weeps", and "Ob-La-Di, Ob-La-Da".

Oakville Centre — AEG Liebherr Auditorium · $75

Sunday, December 13th

10:00AM – 4:00PM

Bronte's 9th Annual Handmade Market

Bronte's 9th annual handmade market at The Royal Canadian Legion features local crafters and handmade gifts. For more information, contact [email protected].

The Royal Canadian Legion

Sunday, December 13th

11:00AM – 4:00PM

Oakville Christmas Market 2026

The Oakville Christmas Market 🎄 brings together local makers, artisans, and small businesses for holiday shopping in the heart of Oakville. Attendees can browse unique handmade gifts, holiday décor, gourmet treats, and one-of-a-kind items while supporting local vendors. Admission is free. Families and friends are welcome. For more information, contact [email protected] or (289) 216-2155.

Hilton Garden Inn Oakville · Free

Sunday, December 13th

1:30PM

Family Holiday Concert

A one-hour orchestral concert celebrating the holiday season for the entire family.

Oakville Centre — AEG Liebherr Auditorium · $48

Sunday, December 13th

3:00PM – 5:30PM

The Great Holiday Cookie Exchange | Oakville 2026

The Great Holiday Cookie Exchange 🍪 Bake It Up! is hosting a festive gathering for cookie lovers and holiday baking enthusiasts. Attendees are invited to bring 24 homemade cookies to exchange, discover new flavours, meet fellow bakers, and take home a box of treats to enjoy. What's included: complimentary coffee, tea, and non-alcoholic beverages while mingling, plus a festive cookie box to fill and take home. Sunday, December 13, 2026 in Oakville, Ontario. Exact location to be announced. Tickets: $49 per person. Limited to 40 participants — reserve your spot early.

Rain Condos Oakville · $39 – $49 CAD + fees

Monday, December 14th

9:00AM – 12:30PM

Oakville Pathfinders Hiking Group

Oakville Pathfinders is an active hiking group for adults aged 50 and up. Members enjoy weekly walks and hikes of varying lengths and difficulty levels — participants choose the distance and terrain that suits them. Up to five hikes are offered Monday and Thursday mornings year-round. Locations include the Bruce Trail, Halton and Hamilton Conservation Areas, Royal Botanical Gardens, Oakville trails, lakefront trails, and more. A valid Town of Oakville Seniors Services membership is required to participate. Memberships are available to residents and non-residents. Each hike has a small fee, payable to the hike leader. For more information, visit https://oakvillepathfinders.blogspot.com/ or email pathfinders1992@gmail.com to ask questions or join.

Meet at the spot designated by the hike leader: the trailhead, or the John Colborne Centre, or the Iroquois Ridge Community Centre. · Free

Wednesday, December 16th

7:00PM – 8:00PM

Cookbook Club

Explore and discuss food culture from around the world. Each session will focus on a specific theme centered on food. Participants can read a fiction or non-fiction book from a curated list. Feel free to try out recipe or two and discuss your experiences in this interactive new book club This month's theme is ________. Registration is required. Please review the guidelines and frequently asked questions on our Program FAQ Skills Learned: Social Skills, Communication Need to cancel? Please let us know. If you have to cancel your spot for any reason, you can do so by: 1. Logging into MyEvents using your library card. If you did not register with your library card, you will need the reference number you received in your confirmation email. 2. Phone your local branch , or email oplreference@oakville.ca. Please have ready the program title, program date, and names of registered individuals. Access to facilities and programs may be impacted by evolving health and safety protocols related to COVID-19. The town will follow all requirements and recommendations issued by Halton Public Health and any applicable provincial regulations. The Town may use discretion to impose its own requirements. You will be notified if your registration is impacted by any changes.

Iroquois Ridge Branch