Events happening in Oakville.

Saturday, November 7th

10:00AM

Oakville Remembrance Trail Run

Oakville Remembrance Trail Run Location: Start and End at Upper Middle Park, 207 McCraney St W, Oakville Time: Starts 10:00 a.m. Join in for the 2nd annual Oakville Remembrance Trail Run! On Saturday, November 7, hit the trails of Lions Valley for an 11km or 5km trail run in honour of our veterans, first responders, and their families. This isn’t just a run — it’s a remembrance movement. All proceeds support Wounded Warriors Canada, helping those who’ve given so much for us. Lace up. Show up. Run with purpose.

Start and End at Upper Middle Park

Sunday, November 8th

7:30PM – 9:30PM

Vivaldi and Company

Vivaldi and Company presents an evening of holiday-season music with the Oakville Chamber Orchestra, featuring works by Corelli, Schubert, Vivaldi, Tchaikovsky, and Bach. The program opens with Corelli's Christmas Concerto, followed by Schubert's dramatic Quartettsatz. Vivaldi's elegant Cello Concerto in D minor (RV407) features Joseph Johnson, Principal Cello of the Toronto Symphony Orchestra, as soloist. After intermission, Mr. Johnson performs Tchaikovsky's lyrical Andante Cantabile, one of the composer's most beloved works for strings. The concert concludes with Bach's Orchestral Suite No. 4, featuring its festive overture, graceful dances, and spirited finale. This program combines Baroque masterpieces with Romantic favourites, showcasing the artistry of one of Canada's leading cellists.

Oakville Centre — AEG Liebherr Auditorium · $50

Friday, November 13th

6:00PM – 9:00PM

Wreath Making Workshop

Participants craft their own wreath in this hands-on workshop. The session welcomes both beginners and experienced crafters and emphasizes enjoying the creative process. Attendees are invited to bring friends or meet others in a relaxed, social setting. The workshop includes all materials, refreshments, and a charcuterie box.

Figaro Coffee House · $125 CAD + fees

Saturday, November 14th

9:00AM – 10:30AM

Oakville Santa Claus Parade 2026

Santa Claus is coming to Town, featuring a North Pole sweets and treats theme. A free Oakville Transit Santa Shuttle runs from Oakville GO Station to Trafalgar Park Community Centre, operating every 5 to 10 minutes with no stops in between. The shuttle service runs from 8 a.m. to 11:30 a.m. Return shuttles to Oakville GO Station operate until 11:30 a.m. The parade starts at 9 a.m. and is expected to end around 10:30 a.m. Arriving early is recommended to avoid missing festivities.

Downtown Oakville and Kerr Village

Saturday, November 14th

9:00AM – 2:00PM

Mary Mother of God CWL Christmas Bazaar

Mary Mother of God welcomes holiday shoppers to browse one-of-a-kind gifts, homemade lunch, and baked goods. The event features a Christmas Café serving lunch, alongside gift stalls offering Advent candles and wreaths, baked goods, preserves, books, CDs, puzzles, crafts, gift baskets, jewelry, purses, a Christmas store, and poinsettias available for pre-order. Free admission and parking. Cash, debit, and credit accepted. For more information, contact [email protected] or call 289-795-9553.

Mary Mother of God Parish · Free

Saturday, November 14th

10:00AM – 4:00PM

Film.Ca Cinemas Christmas Market 2026

The Film.Ca Cinemas Annual Christmas Market is back for 2026! Shop from local artisans, makers, small businesses, and creators with something special to share this holiday season! Be part of one of their favourite annual traditions! 🛍️🎄 For more information, contact Film.Ca Cinemas at (905) 338-6397.

Film.Ca Cinemas

Saturday, November 14th

12:00PM – 2:30PM

Family Holiday Workshop | Clay Wreaths

Oakville Galleries is hosting a family-friendly art activity in Gairloch Gardens on Saturday, November 16, 2026. Participants will design and hand-build their own holiday clay wreaths, guided by instructors through simple clay techniques to create a decoration to keep. For more information, contact Oakville Galleries at [email protected] or 905-844-4402.

Oakville Galleries in Gairloch Gardens

Fri, Nov 20 – Thu, Dec 24

Santa Photos Book Now Special Offer

Photos with Santa 🎅 at Oakville Place Families can book appointments for professional photos with Santa. Sessions run November 20 through December 24. Appointments are popular and book quickly. Pricing: $10 off the Elite package with code SANTA10 at checkout. Offer valid for visits on or before December 11, 2026, and expires November 8, 2026. Cannot be combined with other offers.

Centre Court

Friday, November 20th

5:00PM – 9:00PM

Light Up The Night 2026

Light Up The Night celebrates the holiday season in Downtown Oakville. Attendees can stroll through the area to enjoy holiday lighting, visit Santa, and gather at Towne Square for the annual tree lighting at 6:00 p.m. Participating shops will stay open late, offering an opportunity to begin holiday shopping. For more information, contact [email protected].

Downtown Oakville Towne Square

Friday, November 20th

6:30PM – 7:30PM

Candlelight: The Best of Hans Zimmer

Candlelight: The Best of Hans Zimmer 🕯️ Experience live classical interpretations of Hans Zimmer's iconic film scores performed by a string quartet in the intimate, candlelit setting of Knox Presbyterian Church. The program features music from Inception, The Lion King, Madagascar, Dunkirk, The Pacific, The Dark Knight, Wonder Woman, Gladiator, Interstellar, Dune, Sherlock Holmes, and Pirates of the Caribbean. Performers: String quartet (2 violins, 1 viola, 1 cello). Knox Presbyterian Church, 89 Dunn St, Oakville. Doors at 6:30 p.m. Tickets available online.

Knox Presbyterian Church

Sat, Nov 21 – Sat, Dec 5

HSOMH Holiday Pet Pictures

Capture a festive holiday portrait of your furry, feathered, or scaly friend with a talented volunteer photographer from Karen Dillabough Photography. All proceeds support the Humane Society of Oakville, Milton & Halton's work providing food, medical attention, and second chances for animals in their care. 💙 For more information, follow the Humane Society of Oakville, Milton & Halton on social media.

Ren's Pets

Saturday, November 21st

9:00AM – 2:00PM

St. Dominic Christmas Market

Browse beautiful handmade gifts from local vendors. 🎁 The event features a cozy coffee bar and photo opportunities with Santa. For more information, contact [email protected] or (905) 827-2373.

St. Dominic Parish

Saturday, November 21st

10:00AM – 4:00PM

The Bronte Historical Society’s Christmas Art Show

Celebrate the holiday season at the Bronte Historical Society's Sovereign House, featuring works by local artists. For more information, contact the Bronte Historical Society at (905) 825-5552 or [email protected].

Sovereign House

Saturday, November 21st

3:00PM – 7:00PM

At Home in Bronte for the Holidays 2026

The businesses of the Bronte BIA present At Home in Bronte for the Holidays in Bronte Market Square, with the tree lighting at 5:30 p.m. Bundle up and gather with friends and neighbours to ring in the season together.

Bronte Market Square - 2445 Lakeshore Road W

Wednesday, November 25th

12:00PM – 8:00PM

Local Love Christmas Market at Verace

Meet a curated group of small businesses and artists, discover handmade gifts, and connect with the creative community. After shopping, attendees can enjoy a meal at Verace. ❤️

Verace Italian Restaurant

Thursday, November 26th

5:00PM – 8:00PM

Holiday 100 Exhibition

Summer & Grace Gallery presents Holiday 100, a curated exhibition of smaller works by gallery artists, on view November 26 – February 1. Original artworks range from $100 to $900, offering pieces for personal collections or as meaningful gifts. Opening Reception: Thursday, November 26, 5:00–8:00 PM. Attendees are invited to enjoy artwork, wine, and hors d'oeuvres. Summer & Grace Gallery, 14–323 Church Street, Oakville.

Summer & Grace Gallery · Free

Fri, Nov 27 – Sun, Nov 29

The Nutcracker

The Nutcracker 🎄 brings Tchaikovsky's beloved score to life in this traditional holiday tale. Audiences follow Clara, her Nutcracker, and the magician Herr Drosselmeyer through a whimsical journey to the Land of Snow and the Kingdom of Sweets. The Oakville School of Classical Ballet's production features the school's students under the artistic direction of Amanda Paterson. The performance is family-friendly. For more information, contact the Oakville School of Classical Ballet at [email protected], 905-815-2021, or toll-free 1-888-489-7784.

Oakville Centre for the Performing Arts

Friday, November 27th

10:30AM – 4:00PM

Christmas and Craft Tour

Tour the Erchless Estate, decorated for the season. Visitors can explore Christmas traditions of the past, view classic toys on display, and make a festive craft. For more information, contact the Oakville Museum at [email protected] or (905) 338-4400.

Oakville Museum