Prepare for a holiday adventure in Oakville! Our guide has all the exciting festive events. Whether you're a local or a visitor, our guide showcases the festive magic of Oakville.
Experience the charm of the Santa Claus Parade, where community spirit comes alive with colorful floats and cheerful participants. In addition, the Original Santa Claus Parade features a unique blend of tradition and modern festivities that captivates families each year. And don’t forget that the Hometown Holiday celebration offers a variety of activities that immerse you in the joy of the season. Check out the rest of the page for more details on these and other fun events and activities!
Please contact us if you have suggestions or corrections!
Join the Oakville Discussion!
See the Latest Holiday News for Oakville!
Top Holiday Events In and Around Oakville
- Hometown Holiday
- Original Santa Claus Parade (Toronto)
- Santa Claus Parade
- Santa Claus Parade (Brampton)
- Light up the Night
- Breakfast with Santa & Mrs. Claus - Royal Botanical Gardens (Burlington)
- Santa Claus Parade (Newmarket)
- Horse-Drawn Carriage Rides
- Visit Santa at Santa Cottage
- Santa's Parade of Lights (Oshawa)
See these and even more events listed below!
Oakville Holiday Light Displays
Light up the Night
What to Expect:
Live cappella performances by the CW Carolling Champions.
Description:
Downtown Oakville's Light up the Night event features spectacular holiday lighting, live entertainment by the CW Carolling Champions, Sugar Plums, horse-drawn carriage rides, and visits to Santa's cabin. Participating shops stay open late for holiday shopping.
Where: Oakville | More Info: Light up the Night
Photos with Santa - Winter Festival of Lights
What to Expect:
Free Santa photo opportunity amidst holiday lights.
Description:
Capture a special moment with Santa Claus at the Winter Festival of Lights, where you can enjoy a free photo opportunity amidst the festive atmosphere.
Where: Toronto | More Info: Photos with Santa - Winter Festival of Lights
Santa's Parade of Lights
What to Expect:
Spectacular display of floats and marching bands.
Description:
The Oshawa Santa Claus Parade of Lights features a variety of floats, marching bands, and participants, showcasing a vibrant holiday celebration in Durham Region.
Where: Oshawa | More Info: Santa's Parade of Lights
Oakville Holiday Shows and Entertainment
Rock’n Around the Tree – Holiday Silent Disco
What to Expect:
Silent disco event with iconic Christmas tunes and dancing.
Description:
Join Rock'n Around the Tree – Holiday Silent Disco for a 60-minute session filled with iconic Christmas tunes and dancing under twinkly festive tree lights.
Where: Oakville | More Info: Rock’n Around the Tree – Holiday Silent Disco
Christmas Around the World
What to Expect:
Cultural celebration with international music, dance, and food.
Description:
Christmas Around the World is a cultural event featuring traditional music, dance, and food from various countries, celebrating the holiday season with international flair.
Where: Oakville | More Info: Christmas Around the World
Santa Claus Parade
What to Expect:
Spectacular parade with floats and marching bands.
Description:
The Brampton Santa Claus Parade is a festive event featuring floats, marching bands, and of course, Santa Claus, celebrating the holiday season in Brampton, Ontario.
Where: Brampton | More Info: Santa Claus Parade
Original Santa Claus Parade
What to Expect:
Iconic parade featuring elaborate floats and celebrity clowns.
Description:
The Original Santa Claus Parade is a beloved annual event in Toronto, celebrating hope, family, and love with colorful floats, marching bands, and celebrity clowns.
Where: Toronto | More Info: Original Santa Claus Parade
Oakville Other Holiday Activities
Hometown Holiday
What to Expect:
Holiday celebration with historical charm and international cuisine.
Description:
Downtown Oakville transforms into a vibrant holiday destination with historical buildings, trendy boutique shops, and international cuisine. The event features spectacular Winter Wonderland lights, charming store displays, and various holiday events.
Where: Oakville | More Info: Hometown Holiday
Santa Claus Parade
What to Expect:
Long-standing community tradition with a rich history.
Description:
The Oakville Santa Claus Parade is an annual event celebrating 76 years of community joy, featuring a festive procession through Downtown Oakville.
Where: Oakville | More Info: Santa Claus Parade
Visit Santa at Santa Cottage
What to Expect:
Santa's roaming visit through Downtown Oakville before settling in his cottage.
Description:
Meet Santa at his cozy cottage in Centennial Square, where he will roam the streets of Downtown Oakville before settling in for booked appointments. All proceeds support the United Way Halton.
Where: Oakville | More Info: Visit Santa at Santa Cottage
Horse-Drawn Carriage Rides
What to Expect:
10-minute scenic ride through historic Downtown Oakville.
Description:
Take a leisurely horse-drawn carriage ride through historic Downtown Oakville, enjoying the charming neighborhood scenery and festive atmosphere.
Where: Oakville | More Info: Horse-Drawn Carriage Rides
Visit Santa at Magical Christmas Forest - Kortright Centre for Conservation
What to Expect:
Family-friendly holiday event with Santa and festive activities.
Description:
Visit Santa at the Kortright Centre for Conservation, where families can enjoy a festive atmosphere filled with lights, crafts, activities, and horse-drawn wagon rides. Treats and a visit with Santa in his cabin make for a memorable experience.
Where: Vaughan | More Info: Visit Santa at Magical Christmas Forest - Kortright Centre for Conservation
Christmas at the Farm - Downey's Market
What to Expect:
Traditional farm activities and baked goods during the holiday season.
Description:
Christmas at the Farm - Downey's Market offers a delightful winter tradition with festive activities, farm-fresh treats, and a charming atmosphere.
Where: Brampton | More Info: Christmas at the Farm - Downey's Market
Santa Claus Parade
What to Expect:
Interactive parade with costume characters and festive floats.
Description:
Welcome Santa Claus to Newmarket at the annual Santa Claus Parade, featuring festive holiday floats and a special guest, jolly Old St. Nick. Attendees are encouraged to bring letters for Santa and non-perishable food items for the Newmarket Food Pantry.
Where: Newmarket | More Info: Santa Claus Parade
Breakfast with Santa & Mrs. Claus - Royal Botanical Gardens
What to Expect:
Breakfast with Santa and Mrs. Claus in a serene botanical setting.
Description:
Join Santa and Mrs. Claus for a delicious breakfast buffet at the Royal Botanical Gardens. Enjoy a morning meal with festive company and then explore the beautiful gardens.
Where: Burlington | More Info: Breakfast with Santa & Mrs. Claus - Royal Botanical Gardens
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Burlington (9 miles)
- Mississauga (9 miles)
- Milton (11 miles)
- Mimico (14 miles)
- Islington-City Centre West (14 miles)
- Etobicoke (15 miles)
- Stonegate-Queensway (16 miles)
- Hamilton (16 miles)
- Brampton (17 miles)
- High Park-Swansea (17 miles)
- Willowridge-Martingrove-Richview (17 miles)
- High Park North (18 miles)
- South Parkdale (18 miles)
- Rockcliffe-Smythe (18 miles)
- Grimsby (18 miles)
- Kingsview Village-The Westway (18 miles)
- West Humber-Clairville (19 miles)
- Niagara (19 miles)
- Dovercourt-Wallace Emerson-Junction (19 miles)
- Waterfront Communities-The Island (20 miles)
- Oakwood Village (20 miles)
- Bay Street Corridor (21 miles)
- Annex (21 miles)
- Church-Yonge Corridor (21 miles)
- Mount Olive-Silverstone-Jamestown (21 miles)
- Moss Park (21 miles)
- Downsview-Roding-CFB (22 miles)
- Glenfield-Jane Heights (22 miles)
- Rosedale-Moore Park (22 miles)
- Ancaster (22 miles)
- South Riverdale (22 miles)
- Englemount-Lawrence (22 miles)
- Toronto (23 miles)
- Mount Pleasant West (23 miles)
- Black Creek (23 miles)
- Bedford Park-Nortown (23 miles)
- York University Heights (24 miles)
- Thorncliffe Park (24 miles)
- The Beaches (25 miles)
- East End-Danforth (25 miles)
- Westminster-Branson (25 miles)
- Flemingdon Park (26 miles)
- Banbury-Don Mills (26 miles)
- Willowdale (26 miles)
- Willowdale East (26 miles)
- Newtonbrook West (26 miles)
- Birchcliffe-Cliffside (27 miles)
- Clairlea-Birchmount (27 miles)
- Bayview Village (27 miles)
- Parkwoods-Donalda (27 miles)
- Wexford/Maryvale (28 miles)
- Vaughan (28 miles)
- Don Valley Village (28 miles)
- Dorset Park (29 miles)
- St. Catharines (29 miles)
- Guelph (29 miles)
- Eglinton East (30 miles)
- Tam O'Shanter-Sullivan (30 miles)
- L'Amoreaux (30 miles)
- Steeles (31 miles)
- Bendale (31 miles)
- Agincourt South-Malvern West (31 miles)
- Woburn (32 miles)
- Richmond Hill (32 miles)
- Agincourt North (32 miles)
- Cambridge (32 miles)
- Milliken (32 miles)
- Caledon (33 miles)
- West Hill (33 miles)
- Malvern (34 miles)
- Markham (36 miles)
- Rouge (36 miles)
- Brantford (37 miles)
- Orangeville (38 miles)
- Welland (39 miles)
- Fergus (39 miles)
- Niagara Falls (39 miles)
- Aurora (40 miles)
- Niagara Falls (40 miles)
- Brant (40 miles)
- Pickering (42 miles)
- Kitchener (42 miles)
- Stouffville (42 miles)
- Waterloo (42 miles)
- Ajax (43 miles)
- Newmarket (43 miles)