Celebrate the Holiday Season in Oakville this December

Every winter Oakville transforms into a must-visit holiday destination. With an array of boutique cafes, holiday-themed events and markets, light displays, and local stores that will make you feel like you have been transported into a winter wonderland. Grab your mittens, hat, and holiday cheer and head to Oakville this December.

Day One:

Check-In at Your Hotel

Check in at your hotel before hitting the Town. Visit our accommodations page to view the list of Oakville hotels. Two hotels have created holiday packages available during the festive season.

Holiday Inn Oakville Centre has put together a Festive Family Escape package which includes breakfast, a $25 gift card to Oakville Place, a complimentary map of nearby shopping and market areas, late checkout (subject to availability), and a seasonal treat. Offer is valid until January 4, 2026.

Homewood Suites By Hilton Toronto– Oakville’s holiday offer includes 15% off their best available rate and a welcome goodie bag at check-in. Offer is valid until December 22, 2025. (Corporate booking ID is 3228093).

Get in the Holiday Spirit in Downtown Oakville

Your first destination after you’ve checked into your hotel is downtown Oakville. It is easy to get into the holiday spirit walking the streets of downtown Oakville. Many businesses have decorated their storefronts in creative ways to celebrate the holiday season.

Fun Fact: The movies A Very Jonas Christmas and The Santa Clause filmed some of their scenes in downtown Oakville! Watch the trailer for the Jonas Brother’s new Christmas movie and you will see the Queen’s Head; a British style restaurant located in the heart of Oakville. Watch the opening scene of The Santa Clause to see actor Tim Allen drive through downtown Oakville.

For those looking to do some holiday shopping you are in luck! Downtown Oakville is home to many stores that are must-visit shopping destinations. For those with a sweet tooth visit Chocolate and Love. This shop has a wide variety of chocolate bars and chocolate bombs that would make great stocking stuffers. For the fashionistas out there, there are many clothing stores to visit including: Anthropologie, MUST Boutique, Lemonwood, and lululemon.  For those who aren’t finished with spooky season, visit the Witch’s Fix. This store features home decor, candles, incense, jewellery, tarot cards, and books that allow you tap into your intuition. Drive or walk to nearby Kerr Village to continue shopping. Lords of War Games and Hobbies is a great store to shop for those who enjoy role-playing games, board games, or cards. While in Kerr Village, visit My Back Shed for home décor goods and self-care products. No matter who you are shopping for, you will be able to find the perfect gift in Oakville.

After you have finished shopping, visit a restaurant in downtown Oakville for lunch. Café De Madrid is a charming cafe that serves authentic Spanish cuisine.

After lunch, cross the street and visit the newly opened Velvet Moo for a coffee, tea, or hot chocolate to take with you as you hit the streets of Downtown Oakville again. The Hometown Holiday event will take place every Saturday from November 29 – December 20 in Downtown Oakville. Take a horse-drawn carriage ride, visit with Santa, or enjoy the candy cane carolers as they serenade you with Christmas classics. The event takes place from 12:00 p.m. to 4:00 p.m.

For your next stop, head to Trafalgar Park for some outdoor skating. Helmets and skates are available to rent at the rink during business hours. Spend the afternoon skating at Trafalgar Park. 

After you have finished skating it’ll be time for dinner. Visit 7 Enoteca located in Towne Square, this must-visit restaurant was a recent recipient of the MICHELIN Bib Gourmand Distinction in September 2025.   

End your evening with a performance at the Oakville Centre for the Performing Arts. Notable holiday-themed performances are: The Oakville School of Classical Ballet’s The Nutcracker, a John McDermott Family Christmas, The Oakville Symphony’s Family Holiday Concert, and the BurlOak Theatre Group’s Snow White & the Secret Vault: A Holiday Pantomime.

Day Two:

Lakeside Strolls and Holiday Films

Start your morning with breakfast at Pur and Simple in Bronte Village. This brunch restaurant is sure to impress with their pancakes, crepes, avocado toast, and omelets. Pur and Simple is located in Bronte Market Square which is also home to the Bronte Village Christmas tree starting on November 22.

Once you are finished with your meal, continue your journey down Bronte Road to explore the shops in Bronte Village. Notable shops include Lakeside Livin’, My Girlfriend’s Closet, and Simply Green Baby.

After you have explored Bronte Village, head to Kerr Village for lunch at Narenj where you can enjoy the beautiful ambiance and delicious Mediterranean and Persian food.

We know that December can be busy and at times stressful, which is why it’s important to take time to relax and pamper yourself. Book a massage at one of the many spas in Oakville and let the stress of the season melt away. Rosewater Spa in Downtown Oakville won Visit Oakville’s Talk of the Town award for best spa. Rosewater Spa offers several different spa options such as a hot stone therapy massage, deep tissue massage, aroma therapy massage, couple packages, facials, and more. Treat yourself to a relaxing afternoon in Oakville.   

After your relaxing spa treatment, your next destination will be Coronation Park. Grab a warm drink at Vereda Central, Visit Oakville’s Talk of the Town winner for best Café before heading to the park. Every December, Coronation Park is transformed into a spectacular winter destination. The park will be decorated with over 100,000 lights during the winter season, The Holiday Lights by the Lake display starts December 1 and runs throughout the holiday season.

After you have enjoyed the light display at Coronation Park, visit J.A.C’s Bistro for dinner. J.A.C’s Bistro’s menu is a mix of rustic Italian and French cuisine.

After dinner, catch a movie at Film.ca. This independent movie theatre is showing Christmas staples like Love Actually, Elf, It’s a Wonderful Life, National Lampoon’s Christmas Vacation, and Dr. Seuss’ How the Grinch Stole Christmas.

DAY 3:

Heading Home

We hope your time in Oakville helped you get into the holiday spirit. Before you head home, stop in one of Oakville’s bakeries like Tatin Bakehouse or The Sweetest Thing to pick up a yummy treat box to bring back to your friends and family.