It’s the most wonderful time of the year….

And it’s not even December yet!  We’re feeling very festive these last few days as we get in gear for the busy holiday season ahead. With December being a busy month for most of us, it can be difficult to carve out some family time amidst the hustle and bustle of Christmas shopping, last days of school, office parties, family commitments, decorating, baking, etc.  The list truly does go on, doesn’t it?  As working moms, we can definitely relate.  We’ve rounded up a small list of some really great family friendly events happening in the west end this holiday season. Oh and one for the grown ups.  These are all free, fun and walkable.  Enjoy!

Light Up The Night in Bloor West Village

Bloor West Village is about to transform into a holiday winter wonderland! Kicking off the holiday season this weekend, the Bloor West BIA is putting on their annual Light Up The Night festival, complete with a tree lighting ceremony, and free hot chocolate.

This annual event is one of our favourites, when BWV comes to life, more than it already is.  Check out the beautifully decorated  20 foot tree at Jane and Bloor and enjoy a free concert by the 5 Neat Guys, there are also professional carollers strolling around, and you can feel free to join in with them, if you’d like.  There will also be free coffee, hot chocolate and glow sticks!  Like any good festive market, there will be plenty of give-aways and extended shopping hours at many of our favourite BWV shops.

Over the weekend, keep an eye out for Santa’s Village, popping up at the corner of Bloor St. West and Willard Ave. Here you’ll find more live entertainment, free photos with Santa, cookie decorating, and holiday gift shopping at the artisan marketplace.  There is also a pancake breakfast, not to be missed! The cost for this is $5 per child and $10 per adult with all proceeds going directly to local food banks.

The BWV Light Up The Night festival starts Friday November 25th from 6PM to 9PM

Window Wonderland in The Junction

This is a very unique event, in fact it is the only event of its kind in the entire city. This magical event is free and features 20 unique augmented reality installations, featuring the work of 40 local artists.  Not sure what we’re talking about?  Let us explain.  Stroll along the Junction strip, aim your smartphone at the store front of any of the participating businesses and enjoy an augmented reality show put together by local artists. Still not sure?  Head down to the Junction strip this weekend and see for yourself.  This is a really fun event that is absolutely worth checking out. The Window Wonderland kicks off on November 25th.  Next month, you’ll also be able to catch The Alpine Merry Sheep Choir, a family- friendly performance of funny, heart-warming sheep singing Christmas carols along Dundas Street West.  Catch the sheep from December 3rd until the 24th from 2-4PM.

Window Wonderland in The Junction kicks off on November 25th until January 1st

The CP Holiday Train

This annual family favourite is set to return his year, for the first time since 2019!  Catch the magical holiday train on November 29th at 8:15PM at 750 Runnymede Road at the CP Office Yard Parking lot.  There will also be live performances from Tennille Towns and Asyanbee from 8:30-9:00PM.  This is a fantastic, festive and fun little treat for the entire family.  Though the event is free to attend, there are donation bins around the area for non-perishable food or cash donations.  Since its inception in 1999, the CP Holiday Train initiative has raised over $21 million and collected over 5 million pounds of food. What better way to get into the giving holiday spirit than that!  Don’t forget, this is an outdoor event, so bundle up!

The CP Holiday Train will be rolling through the west end on November 29th at 8:15PM. Catch the train at 750 Runnymede Road at the CP Office Yard Parking Lot

Miracle On Bloor Street in Bloordale

This one is for the grown ups, sort of.  Kiddos are welcome until 8PM and after that, its a grown up night out. The Miracle On Bloor Street is taking over the space at 875 Bloor St from November 18th until December 31st.

Pop into 875 Bloor St. West, near Ossington ave. to a space completely transformed into a Christmas wonderland extravaganza.  Enjoy holiday themed drinks, and incredibly Instagram-worthy decor and festive vibes all around.  It is recommended to wear your ugliest Christmas sweater if you’re popping in, but don’t worry, you’ll match the decor and probably get some great selfies, too.  If that isn’t enough to get you feeling festive, know that the bar is also donating $1 from every drink sale to Nellie’s Shelter, a shelter dedicated to providing shelter, education and advocacy for women and children in the GTA.

Miracle On Bloor will also be hosting a handful of holiday drag shows, check their Instagram for exact dates and details.

Pet Photos with Santa at Dufferin Mall

Of course the baby pictures with Santa are a definite rite of passage for many little ones, but what about your pet? The Dufferin Mall Santa so graciously set aside some time this year to take some photos with all the pets on his nice list. Bring you cats, dogs, puppies and kittens and have some professional festive snaps taken for next year’s Christmas card.  You can even be in the photos as well. if you like. This cute holiday tradition is up and running again this year at the west end’s favourite landmark, the Dufferin Mall. 

Reservations are encouraged, however you can show up and wait in line as well.  Check the Dufferin Mall Website for more information.

Letters To Santa at Nested Real Estate

Last but not least, and back by popular demand, it’s our annual Letters To Santa event.  Every year we deck out our office in true Nested style holiday spirit, and set up our big red “Santa’s Mailbox.” Come see what it’s all about, stop by our office at 639 Annette St. To pick up a custom Santa Letter Postcard, located in a plastic box just outside our front door, or bring your own letter for Santa and drop it into our very special red mail box with a direct line tot he Big Man himself!  This event is free for anyone to take part in and Santa actually writes back to all the letters received.  The drop off deadline is December 7th, after that we send all the letters off to Canada Post and on their way to the North Pole

Nested Real Estate is located at 639 Annette St. Right at the corner of Annette and Durie.  You can’t miss the big red mail box!