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Oakville activities and events allow us to delight in Christmas cheer every holiday season! As we roll into winter, the kids look forward to spending special time with their families during festive events. The holidays bring warm celebrations with Santa, holiday shows, religious services and lots of fun and games! Winter snow invites us to bear the cold and hit the slopes or outdoor rink, make a snow man, and delight in the white fluffy coating that brightens the chilly night.

We look forward to sharing special time with the people dearest to us, bonding over the good cheer. Some of our neighbours may not celebrate Christmas, or any holiday tradition, but it is important to be respectful of everyone’s beliefs and welcome them to share in your cheer. This is also a good time to teach your children about values like compassion, giving and sharing.

As always, we’ve found plenty going on as early as November. Look through family shows, outdoor activities, concerts, parades, and much more. To search for a key word press CTRL-F on a PC or CMD-F on a MAC.

Happy Holidays!

Christmas Activities in Oakville

Downtown Oakville Christmas Tree Lighting – Friday November 18th

Join Downtown Oakville’s Annual Ceremony from 7 – 9 pm. The Downtown Oakville Tree Lighting Ceremony will begin at 7 p.m. located in the Town Square to kick off the Christmas season! Enjoy incredible entertainment, caroling, Santa, treats, and of course the lighting of the beautiful tree!
146 Lakeshore Road East – Oakville, ON – (905) 844-4520 –

Christmas Craft Show – Saturday November 19th
Once again Kerr Street Ministries is holding their annual Christmas Craft Show to raise money for their Christmas Wonders Program. This is an outreach program that helps make Christmas more celebratory for the families and individuals in the Kerr Street area of Oakville, where over 26,000 people live below the poverty level. All of the money raised at this event will go directly back to our community. Join them from 10am – 2pm. You’ll find lots of unique gift ideas!
485 Kerr Street – Oakville, ON – 905 – 845-7485 –

Santa Claus Parade Oakville

Oakville Santa Claus Parade – Saturday November 19th
This year’s parade will take place downtown, rain or shine starting at 9:00 a.m. Marvel in the proud theme of a Canadian Christmas! Check out the floats, bands, Santa Claus and loads more fun. The parade route will flow down Lakeshore Road East from Reynolds Street and turn right at Kerr Street, finally veering left at Stewart Street, ending at Felan Avenue. Please bring change, non-perishable food items and toys to donate.
Lakeshore Road East & Reynolds Street – Oakville, ON – 905-815-5981 –

Bronte BIA Christmas Tree Lighting – Saturday November 26th

Bundle up, bring your camera, and come down to Centriller Square on Lakeshore Road. (Opposite Sobey’s at Centriller Square Plaza). From 4pm – 6:30pm experience the mirth and merriment of an old-fashioned Bronte Christmas during the Bronte Business Improvement Area’s Annual Tree Lighting Ceremony. Take time to shop some great early sales and warm up indoors at one of Bronte’s excellent eateries with mulled cider, festive treats or whatever your heart desires.
2410 Lakeshore Road West – Oakville, ON – 905-825-3258 –

Christmas Open House – Weekends November 26th – December 11th

Santa Claus will be dropping by Springridge Farm! The farm is just a short drive from Mississuaga. The day is loaded with Christmas activities for children and families. Paint a glass ball ornament or decorate a freshly baked Gingerbread Cookie to take home. Visit with Santa throughout the barn while enjoying hot cider. See the bakers busy making cookies, fruit pies and tarts for the holiday season.  Please call ahead to place a Christmas baking order 905-878-4908. Plus, Gift Baskets and Gourmet Foods, with dips, sauces, spreads, jams. Springridge Farm – 7256 Bell School Line – Milton, ON –

Santa Visits & Photos – Saturday November 26th

Share your Christmas wishlist and get your photo taken with Santa in the magical setting of Towne Square, from 2;00pm until 4:00 with it’s beautiful Christmas tree, music, holiday treats and more for all ages to enjoy! Photos with Santa is available and FREE to all!
94 George Street – Oakville, ON – (905) 844-4520 –

Wagon Rides & Carolling – Saturdays & Sundays November 26th– December 24th, 2016

Whether you’re finishing your Christmas shopping, preparing your home and self for the holidays, picking up a treat for a host, or out dining and celebrating the season, you can enjoy crossing off your holiday ‘to-do list’ in Downtown Oakville, with wagon rides with Santa throughout the Downtown (pick up in Towne Square) and the melodic sounds of carollers from 1:00pm-4:00 pm

94 George Street – Oakville, ON – (905) 844-4520 –

Kerr Village Christmas Tree Lighitng– Dec 2nd from 5-8pm

This is a local heartwarming event that has continued as a tradition for 22 years and brought many families together to ring in the start of the holiday season.  Special Appearance by Santa, Mrs. Claus, The Elf, McGruff the Crime Dog, Town Crier & Invited Dignitaries.

Heritage Square 340 Kerr St.


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