Celebrate Halloween 2018 in Ossington Village

Ossington Village Halloween

We know where and how you can celebrate Halloween 2018 in Ossington Village. Parties are plentiful, so get your costume ready! October 31st is only a few weeks away and Ossington Village Halloween events start soon.

Fountain Halloween
Art at Fountain by Ceilidh Stidwill, from their instagram

Halloween is all month long at The Fountain

Dundas West art bar Fountain is pulling out all the stops with their annual creepy décor for Halloween. The art bar is showcasing several local artists’ works throughout the bar for the month of October. Stop by any night for a drink and prepare to be frightened because the exhibit includes a murder room. It runs through October 31st.

Fountain, 1261 Dundas Street West


Rocky Horror at Lower Ossington Theatre all monthRocky Horror at Lower Ossington Theatre

LOT‘s annual Halloween tradition includes more opportunities to see Rocky Horror Live all month long. Many of the shows are already sold out, because it’s that popular, so go online to purchase tickets! You know you want to do the time warp in a packed audience on Ossington this month!

Lower Ossington Theatre, 100 Ossington Ave.

Halloween Themed Mystery Show at The Painted Lady, October 18th and 19thHalloween Event Painted Lady Ossington

Ossington music venue The Painted Lady hosts a very unique Halloween Burlesque mystery game for two nights only next Thursday and Friday, October 18th and 19th. Go check out this murder mystery with burlesque at a bar where you can drink! Capacity at Painted Lady isn’t that big so it is likely to sell out. Tickets are available for $20 in advance.

The Painted Lady, 218 Ossington Avenue

Unleashed in the City’s 5th Annual Howl-o-Ween Party and Pup Parade, October 27thUnleashed in the City Howloween

If you have a dog or just like dogs, definitely check out this free Halloween event put on by Ossington dog care shop Unleashed in the City. The holiday inspired dog party runs in the afternoon from 1-3PM and the dogs in costumes are just the cutest. Bring your pup and your camera!

Unleashed in the City, 211 Ossington Avenue



Hey Ghoul Hey – The Garrison’s Halloween Party, Saturday October 27th

Hey Ghoul Hey Ossington Halloween
Hey Ghoul Hey at The Garrison October 27

Celebrate Halloween the Saturday before with DJs at The Garrison. The party is hosted by Sean Beardoncé and features DJ Pekoe and a costume contest with prize money. Festivities begin at 10PM and tickets are already on sale for $10.

The Garrison, 1197 Dundas Street West

CATL Ossington Village HalloweenCATL’s 4th Annual Halloween Bash at The Dakota, October 27th

Another neighborhood tradition, Toronto rock and blues duo catl returns to The Dakota Tavern for a costume filled night of live music. This year, Nashville band Volk joins them onstage. There’s a prize for best costume. Tickets are on sale now for the low price of $10. Wait til the day of, and the price goes up to $12.

The Dakota Tavern, 249 Ossington Ave


Ghost Stories Told Live at The Garrison, October 30th

Toronto’s monthly storytelling event True Stories Told Live hosts a special Halloween themed fundraiser at The Garrison on October 30th. Listen to spooky stories told by a variety of different storytellers, comedians and more. The event page has more details and $10 tickets are already on sale.

The Garrison, 1197 Dundas Street West

Trinity Bellwoods Pumpkin Parade, November 1st

The Friends of Trinity Bellwoods Park are once again hosting this fun and free post-Halloween event using the neighbors’ jack-o-lanterns. Everyone is invited to bring your carved pumpkin to the park, and they’ll all be lit up along the path north of the Recreation Centre. The event runs from 5:30 – 9:30PM and ends with a pumpkin toss right into the compost bins.

Trinity Bellwoods Park, north of the Rec Centre

Day of the Dead at Reposado, November 2ndDay of the Dead Reposado

Celebrate the post-Halloween Mexican holiday Day of the Dead at Reposado Bar on Ossington. This annual event features music, Mexican food and drinks with tequila and mezcal, as is Reposado’s forté.

Reposado Bar, 136 Ossington Avenue, November 2nd at 6PM


We know there are going to be more Halloween events in the next few weeks and we’re just waiting for them to be posted! If you know of an Ossington Village Halloween event we haven’t included please share in the comments or social media! We will keep adding to this post so keep checking back for more info, and also check our calendar regularly.

About Melinda M 604 Articles
Mel, living on a boat, sailing the world. Slowly.