Your Ultimate Guide to Toronto Fall Date Ideas

Festivals, spooky dates, and the perfect ideas for colder weather are here!

At datenight, we always welcome October with open arms! Seasonal drinks and treats, date ideas galore whether you love everything spooky or everything cozy, and so many fun things to do before the weather turns and a long winter arrives. You can find fall dates at virtually every corner you turn in Toronto and the GTA this season, so we’re bringing you the ultimate list of events, festivals, fairs, and farms to check out with your date this October!

See below for the ultimate fall date ideas round-up:

Festivals, Events & Fairs

Nightmarket TO Harvest Festival

Our favourite time of the year is here and we’re thrilled that Nightmarket TO is bringing back the Harvest Festival to Mississauga! NMTO will be hosting a 10-day harvest festival at Square One Shopping Centre with rides, games and a harvest marketplace.

Located: Square One Shopping Centre Lot P3, Mississauga

When: September 30th – October 9th

Toronto Oktoberfest

This is Toronto Oktoberfest’s 10-year anniversary bash, and they’re returning after a two-year COVID hiatus. Just because summer’s done doesn’t mean the party stops, and we can’t wait for this epic fall festival full of music, food, and of course beer!

You and your date can look forward to non-stop fun among Bavarian communal tables and benches direct from Germany lining the Festhalle, an outdoor Bavarian Village, and an atmosphere so authentic you’ll feel like you’ve been transported to Munich.

Located: Ontario Place, Toronto

When: September 30th & October 1st

Fall N Leaves

Calling all fall vibes lovers, and everyone who wants their food to look as on-season as possible! This seasonal pop-up patio is back in the heart of downtown. There’s tons of fall foliage decor for photos, cocktails, food, and fire pits for you to enjoy. But food and drinks aren’t all that’s happening at Fall N Leaves; pick a pumpkin and paint it, lounge on a hay bale sofa, play pumpkin bowling and more. Plus, it’s close to so many fun spots downtown that you can make a whole fall day of it!

Located: 164 Bathurst St, Toronto

When: September 30th – October 16th

Dark Waters at Ripley’s Aquarium

Spend the scariest night of the year with all our creatures of the deep as you explore the depths of the aquarium while enjoying live music, custom bars and spooky snacks.

And make sure to dress for the occasion with the return of their costume contest for a chance to win some JAW-some prizes​!

Located: Ripley’s Aquarium at 288 Bremner Blvd, Toronto

When: October 28th at 8pm

Spooky & Scary Date Ideas

Howland Inn Séance with Jaymes White

If the other horror attractions are baby food for you and your date, this experience is SURE to scare the socks off you. This is truly a once in a lifetime experience (because you may be too scared to go back)!

Jaymes White is a celebrity mentalist, mindreader (and possibly witch), inviting groups of brave souls to a chilling recreation of an authentic Victorian Séance at one of Toronto’s oldest and most haunted Inns.

To be warned: this soul-shaking psychological experience is not intended for the weak or faint of heart.

Located: Meet at the intersection of Howland Avenue and Dundas Street West (at the North East corner bus stop in front of the 4020 Dundas Street West Plaza). You will then be escorted a short walking distance to the Séance Location.

When: Sept 30th – November 26th

Casa Loma Legends of Horror

Usually, Casa Loma is a romantic castle to stroll through, or enjoy garden and terrace dinner dates at. In October, it’s a terrifying immersive horror experience. Brave the castle with your date while walking through a 2 km trail of the castle’s gardens, tunnels and some of the “darkest spaces never open to the public.” As if that’s not scary enough, they’re bringing the castle walls to life, literally, with 3D projections and theatrics.

Located: 1 Austin Terrace, Toronto

When: September 30th – October 31st

Halloween Haunt

What’s spooky season without this staple haunt happening at Canada’s Wonderland? If a wonderland full of opportunities to get scared sounds like your fall cup of tea, you have to make a point of heading here.

There’s a new maze for 2022: PANDEMONIUM.

The dark tunnels under the mountain are no place for humans, especially after dark. When the creatures of the pit awaken, they use their mind-warping tricks and luminescent traps to confuse their prey, luring them to a ghastly demise. The vibrant lights may appear to promise salvation, but they’re only a harbinger of the pandemonium that is about to ensue, as you’re embraced by the cold, dark death of the shadows and the creatures that live within.

Located: 1 Canada’s Wonderland Drive, Vaughan

When: Select nights, September 23rd – October 30th

The Black Lagoon Pop-Up

Black Lagoon is an immersive, creepy-as-hell experience that pays homage to the macabre and throws in a splash of goth and metal for good measure. Wear your costume to these dark dungeons of drink and enjoy innovative and deliciously spooky cocktails!

Located: 875 Bloor st west (upstairs)

When: October 1st – October 31st

Snyder’s Fear Farm

If you haven’t gotten your fix of fear in the city, venture out east and visit Fear Farm in Bright, Ontario this season. The farm has six different haunted attractions you can explore including a hay ride through the haunted grounds, a pitch-black corn maze, a multi-level haunted house, and a carnival.

If you need a bit of a snack after all that screaming then make sure to head over to one of the many food vendors on the farm that will be serving up some of your favourite fall treats including butter tarts and a warm glass of apple cider.

Located: 936685 Blenheim Rd, Bright ON

When: September 24th – October 30th

Fall Farm Date Ideas

Pingles Harvest Festival at the Farm

Celebrate fall on the farm with apple and pumpkin picking, wagon rides for the kids, a giant 6.5-acre corn maze, the Playland, a fall-inspired menu, an on-farm bar, multiple coffee shacks and more! Pingles Farm has been known to up their Harvest Festival game each year with delicious and inventive food and drink items, take-home food for your fall feasts, installations and activities, and market items to purchase!

Located: 1805 Taunton Road East, Hampton

When: Until October 31st; Tues-Thurs 9:30am-6pm, Fri-Sun 9:30am-7pm

During the week (Tuesday – Thursday) enjoy a more peaceful experience, for a discounted rate!  
*No food, live music, wagon rides or pumpkin patch access Tues – Thurs.

Downey’s Farm

Of course these guys made the list. Downey’s Farm has been the site of some iconic fall photography around the GTA with their iconic pumpkin patch and farm-front. Did you know that behind all of that, is an insanely fun Pumpkinfest happening right through the gates? Check out this map for EVERYTHING you can do.

Located: 13682 Heart Lake Rd, Caledon

When: Until October 31st; Daily 9am-5pm

Chudleigh’s Entertainment Farm

If you haven’t been to his Milton farm famous for their delicious Apple Blossom desserts, you need to put it on your list. Walking through the entrance brings you to a whole new fall farm world with a huge patio and live music area, a Cidery to taste flights of their own hard apple cider (and some fun cocktails), rows and rows of apples and pumpkins, farm animals, photo opps, and a market to bring a little but of Chudleigh’s home with you.

The pumpkin patch is now open!

Located: 9528 Regional Road 25, Halton Hills

When: Open daily 8:30am-6pm (Open until 11pm Fridays and Saturdays

Muskoka Lakes Winery & Farm

Johnston’s Cranberries at Muskoka Lakes Farm & Winery have started up their Harvest activities again. Visit this marsh and wade through 400,000 pounds of cranberries with your friends or date for a truly unique experience.

Spend the day at Muskoka Lakes Winery & Farm and go on a wagon tour, have a guided wine tasting, shop for fresh cranberries, and explore the hiking trails with beautiful scenery, too. Open seven days a week!

Located: 1074 Cranberry Rd, Bala

When: September 24th – October 31st

Applewood Farm & Winery

This family-run farm and winery has all the fall aesthetic you need and love for the season. Pick your own pumpkins, get lost is a corn maze, and check out the cute installations and animal enclosures at this spot northeast of the city.

On October 6th, book a Thanksgiving centerpiece workshop that includes wine with Perennial Petals at the farm! Email to register.

October 8th – 10th is Thanksgiving weekend at the farm! Start a new family tradition and join Applewood for fresh air, a giant corn maze and pumpkin patch.

Located: 2055 Saintfield Road, Seagrave ON

When: Open Thurs-Fri 11am-5pm, Sat-Sun 10am-5pm & Thanksgiving Monday 10am-4pm

Drive-Thru & Walk-Thru

Spooktacular Light Show

Experience the largest family friendly Halloween Light Show like none other! Spooktacular Light Show will be featuring over 2 million lights on a 2KM route of your family fun favourite characters, pumpkin filled drive thru tunnel, from 2D to 3D displays, music lights and much more this Halloween season!

Located: Meadvowvale GO Station, Mississauga & Richmond Hill GO Station, Richmond Hill

When: September 23rd – October 31st

Pumpkins After Dark

Pumpkins After Dark is Canada’s award-winning outdoor Halloween event. Featuring over 6,000+ hand-carved pumpkins, this one-of-a-kind walk-through experience is the must-see event of the fall season. Grab some car snacks and drive your way through a 2.5km tunnel and trail of light installations. The whole event will take you around 45 minutes to one hour, perfect for heading out to dinner in the area afterwards!

Located: Country Heritage Park at 8560 Tremaine Road, Milton

When: September 23rd – October 30th

Halloween Nights of Lights & Pumpkinville

Taking place at CF Sherway Gardens from September 30 to October 31, 2022, Halloween Nights of Lights will now be a thrilling, immersive walk-through experience for the 2022 season.

Bigger and better, this year’s experience will feature more than 1.5 million LED and RGB lights animated and synchronized to your favourite Halloween tunes. Continue the fun inside Pumpkinville, a fun fair located at the end of the Nights of Lights trail featuring larger-than-life pumpkin sculptures and village featuring over 30,000 pumpkins.

Located: CF Sherway Gardens at 25 The West Mall, Etobicoke

When: September 30th – October 31st

Little Canada

Have you ever wanted to take a glance at Canada from the view of a giant? Well, we can’t make you bigger, but Little Canada can bring a miniature version of the country right to your doorstep.

Situated just off of Yonge-Dundas Square and marked with a colourful entryway, Little Canada takes you off the streets of Toronto and into a miniature version of landmarks and cityscapes from all over the country.

This is perfect for rainy days, staycations or travels into the city, or pairing with a restaurant or event near-by!

Located: 10 Dundas St E., Basement2, Toronto

When: Permanent attraction, open daily 10:30am-7:30pm


The Bentway and Exhibition Place invite you to experience Confluence, a massive, immersive installation within a hidden chamber under the Gardiner Expressway, inspired by the water systems that have shaped Toronto.

Created by Maine-based artist duo Striped Canary (Stephen B. Nguyen and Wade Kavanaugh), and featuring a sound field composed by Anne Bourne, Confluence asks visitors to reflect on how humans have shaped natural environments, how our urban landscape has changed over time, and how the built and natural worlds can meaningfully co-exist in the future.

Located: Under the Gardiner at Exhibition Place

When: Wednesdays to Sundays October 1st – 30th

Nuit Blanche

Nuit Blanche, Toronto’s all-night celebration of contemporary art, returns from sunset on October 1 to sunrise on October 2 for its biggest event ever.

Expanding to include exhibitions in Etobicoke and North York, in addition to downtown and Scarborough, the long-awaited event features more than 150 artworks by local, national and international artists.

Located: 10 Dundas St E., Basement2, Toronto

When: October 1st, 7pm-7am

Psychedelics: The Experiential Exhibition

Toronto is celebrating with a captivating, eye-popping experiential art exhibition. Have your mind-expanded, and perspective changed, with this enlightening trip through the long, strange history of psychedelic substances, from their origins in indigenous healing rituals, to their current applications in Western clinical therapy.

The exhibition guides viewers through a series of curated spaces, each devoted to a different psychedelic substance and its historical or traditional uses.

Located: Lithuanian House at 1573 Bloor St. W, Toronto

When: September 30th – October 30th (Wednesdays through Sundays)

We’re sharing more date ideas throughout this season from all things haunted, to all things pumpkin spice, and more. Stay tuned and keep your eyes peeled here for the best Toronto and GTA date ideas!

datenight – your experience destination across Canada Established in 2013, we are the trusted source for all things dating.




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datenight – your experience destination across Canada Established in 2013, we are the trusted source for all things dating.




British Columbia




datenight Game

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