Events happening in Oakville.

Fri, Nov 27 – Sat, Nov 28

OWEC Annual Gala: Old Hollywood

An evening of wine, food, and dancing. Attendees will enjoy a sparkling wine cocktail hour with an appetizer bar, followed by a seated 4-course dinner paired with curated wines. Live dance music plays throughout the night, with wine and beer stations available. For more information, contact [email protected] or 905-483-7286.

St. Joseph's Banquet & Conference Centre · $145 CAD + fees

Saturday, November 28th

9:00AM – 12:00PM

Visit with Santa

Santa is visiting the Museum. Guests can write a letter to Santa at the Old Post Office in Lakeside Park, tour the Erchless Estate decorated for Christmases past, and enjoy activities in the Coach House before meeting Santa in his sitting room. Bookings are 30 minutes long. The visit is for ages 3–10 plus accompanying adults. For more information, contact the Oakville Museum at [email protected] or (905) 338-4400.

Old Post Office

Saturday, November 28th

10:00AM – 4:00PM

Appleby College Parents’ Association Holiday Market

This festive market features vendors offering contemporary and unique gifts, along with a selection of sweet and savoury treats, seasonal favourites, and specialty foods and beverages. Attendees can enjoy festive holiday music performed by Appleby students, participate in complimentary holiday-themed workshops, and ice skate with family and friends. Those planning to skate should bring their own skates and helmets. No sticks are permitted. This is a free community event, open to all. For more information, contact [email protected].

Appleby College · Free

Saturday, November 28th

10:30AM – 3:30PM

Saturday Youth Workshop: Holiday Cards

Oakville Galleries is hosting a Holiday Youth Workshop led by instructor Meghan. Participants will learn simple linocut printmaking techniques to design and hand-print their own festive greeting cards and postcards — perfect for friends, family, teachers, or anyone on a holiday gift list. This is a hands-on, 2-hour workshop. No experience is necessary; all skill levels are welcome. Each participant will complete a finished artwork to take home. For more information, contact Oakville Galleries at [email protected] or 905-844-4402.

Oakville Galleries in Gairloch Gardens

Sat, Nov 28 – Sun, Nov 29

Oakville Art Society's Holiday Art Market

The Oakville Art Society hosts 30+ local artists over two days, showcasing handmade paintings, jewellery, fluid art, and other original creations. Each table displays the individual style and work of an Oakville Art Society member. For more information, contact [email protected] or 905-827-5711.

Oakville Art Society

Sat, Nov 28 – Sun, Nov 29

Holiday Inn Oakville Centre Christmas Market

The second annual Christmas market features 41 local vendors showcasing Canadian-made goods and gifts. Shoppers can browse the vendor stalls, take photos with Santa, and enjoy holiday music performed by a church choir. Entry requires a non-perishable food donation. For more information, contact [email protected].

Holiday Inn Oakville Centre

Saturday, November 28th

2026 Kerr Village Christmas Tree Lighting & Holiday Market

Kerr Village's Christmas Tree Lighting 🎄 is a tradition spanning more than 30 years. The event has grown and expanded throughout its history. This year's celebration takes place in Westwood Park on Saturday, November 28.

Westwood Park

Sat, Nov 28 – Sun, Nov 29

G.F. Handel's Messiah

G.F. Handel's Messiah 🎵 This annual holiday tradition features an uplifting performance by choir and orchestra at St Andrew's Catholic Church. Performances are November 28 at 8:00 p.m. and November 29 at 3:00 p.m. at 47 Reynolds Street, Oakville. For more information, contact [email protected] or 905-399-9732.

St Andrew's Catholic Church · $0 – $49.26 CAD

Sunday, November 29th

2:00PM – 4:30PM

Kinusaiga Craft Afternoon - Oakville

Kinusaiga is an easy, no-sew craft that creates a unique fabric mosaic artwork. Participants can choose from Christmas or standard designs and select from a variety of fabrics. All materials and supplies are provided, and the session is fully guided. Light refreshments will be served.

Queen Elizabeth Park Community and Cultural Centre · $50 CAD + fees

Tuesday, December 1st

12:00PM – 8:00PM

Local Love Christmas Market at Tabule

Meet a curated selection of talented small businesses and artists, discover handmade gifts, and connect with the creative community behind Inamullumani's markets. After shopping, guests can enjoy a meal at Tabule, which offers Middle Eastern cuisine.

Tabule

Thursday, December 3rd

6:00PM – 8:30PM

Adult Holiday Cards Printmaking Workshop

Oakville Galleries is hosting a hands-on printmaking workshop where attendees will design and manually print their own holiday greeting cards using linocut techniques. Participants will create multiples of their design, taking home a collection of handmade flat cards and postcards. No prior experience is required. Wine and light refreshments will be served. For more information, contact Oakville Galleries at [email protected] or 905-844-4402.

Oakville Galleries in Gairloch Gardens

Fri, Dec 4 – Mon, Feb 15

Holiday Lights by the Lake 2026

Holiday Lights by the Lake transforms Coronation Park into a festive winter destination with an elaborate light display. The lights are on display from December 4 through February at Coronation Park, 1426 Lakeshore Road West, Oakville. For more information, contact the organizers.

Coronation Park

Friday, December 4th

8:00PM – 10:00PM

Rowdymen Christmas

Legendary guitarist Gerry Finn (Burton Cummings, Killer Dwarfs, David Usher) and George Masswohl, star of the musical stage (Come From Away, Stratford Festival, Shaw Festival), return to the Oakville Centre with their popular Christmas programme. A Newfoundland Christmas with The Rowdymen features traditional music, stories, and Christmas tunes from Newfoundland and beyond. The evening offers a festive blend of song and storytelling.

Oakville Centre — AEG Liebherr Auditorium · $65

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

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

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