Legends of Horror at Casa Loma
The historic castle grounds and subterranean stone tunnels transform into an immersive 2 km theatrical walk, lit dramatically under the October night sky.
halloweennightlifehistoric
For friend groupsThings to do in Toronto with friends this weekend (Oct 16–18)
This weekend in Toronto: Fri, Oct 16 – Sun, Oct 18, 2026 · 7 dated events
What's on in Toronto, Canada this week — the spots locals are packing, buzzy restaurants, and weekend plans worth texting the group chat about.
13 hand-picked things to do in Toronto, Canada right now · 7 with confirmed dates
Photo: Nathalia Segato / Unsplash
How we pick spots for a group
- Buzzy, higher-energy rooms that take a crowd
- What's on right now over evergreen tourist stops
- Bookable tables and shared plates a group can split
🍁 Happening Today
Events and things to do tonight
Toronto Maple Leafs vs. New York Islanders
Saturday night hockey in downtown Toronto as the Maple Leafs host the New York Islanders on home ice under the Scotiabank Arena lights.
hockeysportsdowntown
How to Train Your Dragon 2 in Concert
A full live symphonic orchestra performs John Powell's soaring score live-to-film on the massive Meridian Hall screen this afternoon.
orchestrafilmfamily
Plan a friends trip to Toronto, Canada
Tell us who's going and WonderKit drafts three Toronto, Canada trip ideas in about a minute — free, and you see them before creating an account.
☕ Eat & Drink
Saturday brunch and seasonal dining
Blueberry Hill Brunch at Old School
Stacked-high scratch buttermilk pancakes smothered in hot blueberry compote and brown sugar butter, paired with house-cured bacon in a vintage diner room.
brunchcomfort-foodclassic
Autumn Farm Breakfast at White Lily Diner
Michelin Green Star diner cooking with regenerative produce from their Uxbridge farm; order the house-smoked bacon, hash browns, and warm crullers.
farm-to-tablebreakfastcraft-beer
Wood-Fired Sicilian Plates at Bar ARDO
Freshly recognized on Michelin's recommended roster, this intimate King East sibling serves blistered sourdough pizzas, raw seafood, and spiced amaro cocktails.
italianwine-barcozy
🎟️ This Weekend in Toronto, Canada · Oct 16–18
Concerts, autumn walks, and weekend energy
Bruce Cockburn at Massey Hall
The Canadian folk-rock poet and guitar master steps onto Massey Hall's warm, historic wood stage for an intimate career retrospective.
folklive-musichistoric-venue
Buena Vista Orchestra at Danforth Music Hall
Classic Havana son, guajira, and bolero rhythms taking over the Danforth, channeling the vibrant, brassy energy of traditional Cuban big band.
latinlive-musicdance
Fall Foliage Walk at High Park & Grenadier Pond
Mid-October brings peak gold and amber across the black oak savannah. Grab a hot cider from Grenadier Cafe and loop the 5 km dirt trails.
outdoorsfall-foliagewalking
✨ New & Notable
Fresh honors and seasonal highlights
aKin's Contemporary Asian Tasting Menu
Chef Eric Chong's downtown counter freshly celebrated its Michelin Star, delivering high-concept courses of abalone, rich broth, and seasonal Ontario game.
fine-diningmichelintasting-menu
Halloween Harvest Festival at Bradley House
Step into 19th-century hearth cooking, cider pressing, and heritage autumn craft demonstrations on the forested Bradley Museum grounds.
heritageharvestfamily
🚗 Quick Escape
Easy autumn escapes under 3 hours away
Grape Harvest & Farmstands in Prince Edward County
Drive 2.5 hours east down the 401 to Hillier and Wellington during grape pressing. Sip cool-climate Pinot Noir at Closson Chase's purple barn and sample local sharp cheddar along rural country lanes.
wine-countryroad-tripharvest
Limestone Cliffs and Cider in Elora
Just 90 minutes west of the city, hike the dramatic cedar-lined rim of Elora Gorge, browse stone artisan boutiques along the Grand River, and warm up over dry farmhouse cider.
hikingsmall-towngorge
Ready-made Toronto, Canada itineraries
Ready-made plans for Toronto, Canada, written out in full and built from real local spots — start from one instead of a blank page.
Frequently asked
What are the best things to do in Toronto, Canada with friends?
Group-friendly highlights in Toronto, Canada right now include Legends of Horror at Casa Loma, Toronto Maple Leafs vs. New York Islanders, and How to Train Your Dragon 2 in Concert. WonderKit updates this guide daily so plans stay current.
Where do locals go out in Toronto, Canada?
The "Eat & Drink" section above lists buzzy restaurants and bars in Toronto, Canada — the spots locals are actually packing this week.
Where's the best nightlife in Toronto, Canada?
Check the sections above for current events, buzzy bars, and weekend plans in Toronto, Canada worth texting the group chat about.
Plan a friends trip to Toronto, Canada
Tell us who's going and WonderKit drafts three Toronto, Canada trip ideas in about a minute — free, and you see them before creating an account.