Your Ultimate Toronto Fall Date Ideas Bucket List

pumpkins after dark

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 month, so we’re bringing you the ultimate list of events, farms, dessert shops, and wineries you can take your date this October for the most fall vibes.

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


1. Halloween Haunt

What’s spooky season without this staple GTA event 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.

New attractions for 2021 include the Kingdom of Carnage, Streets of the Undead, and The Farmstead; in case there weren’t already enough scary spots to check out.

Located: 1 Canada’s Wonderland Drive, Vaughan

2. Pumpkins After Dark

Experience Canada’s award-winning largest outdoor Halloween event featuring thousands of hand-carved pumpkins and live carving demonstrations. Grab some car snacks and drive your way through Pumpkins After Dark, a 2.5km tunnel and trail of light installations like no other. The whole event will take you around 45 minutes to one hour, perfect for heading out to dinner in the area afterwards!

Located: 8560 Tremaine Road, Milton

3. 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

4. The Eatonville Farmhouse 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 is a celebrity mentalist, mindreader (and possibly witch),inviting groups of 13-16 guests to a chilling recreation of an authentic Victorian Séance. Happening until November 27th.

Located: 555 Burnhamthorpe Road #102, Etobicoke (meet infront of The Red Cardinal Tavern)

5. Fall N Leaves

Calling all foodies looking for their next non-spooky date night. 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


1. Pingles Farm Market

This year, there’s two different ways to experience the farm during October! For the best fall date, head over during weekends to enjoy the Harvest Festival with activities like their Alice in Wonderland 6.5 acre corn maze, the Playland, a wagon ride, pick your own apples and pumpkins, and some delicious looking seasonal treats.

Offering their full dine-in menu, you won’t even have to find somewhere else to eat. What we recommend for the ultimate fall day? Chunky Chili Poutine, Maple Bacon Chicken & Waffles, house-smoked Brisket on a Bun, the Pingles Donutwich, Apple Pie Funnel Cake, and their delicious fall drinks with fun sweets on top.

Hallowoof Day for your doggy dates is happening on Saturday October 30th too!

Located: 1805 Taunton Road East, Hampton

2. Carl Laidlaw Orchards

You don’t have to venture too far outside of Toronto for this farm! Carl Laidlaw Orchards has fun going on all month at their farm. Their installations are some of the most unique we’ve seen, you definitely need some photos of you and your date here.

Located: 9496 Heritage Road, Brampton

3. 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

4. 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. We personally recommend this date idea!

Located: 9528 Regional Road 25, Halton Hills

5. Merry Farms

Head west out to Hamilton for your next cute fall farm date! Merry Farms is now open for Pumpkinfest season. Admission includes over 30 activities like a Pedal Kart track, farm animals, barnyard basketball, a corn maze, Tractor Pull, a 65′ long bouncy pumpkin. pumpkin bowling, a corn pit, Hay Bale Mountain. giant slides, wagon ride through the Christmas tree fields & so much more. No reservations required!

Located: 1974 Concession 2 Rd W, Hamilton

6. 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 legendary farm is back to bring those who dare enter haunted hayrides, creepy cornfields that you’ll definitely need to hold onto your date tight to get through it, and the spooky Hiller House.

Located: 936685 Blenheim Rd, Bright

7. 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, and explore the hiking trails too. Open seven days a week!

Located: 1074 Cranberry Rd, Bala

8. Brantwood Farms

What doesn’t this farm have for you and your date? Their fall festival happens every weekend in October and has events and activities that include hayrides, a giant jumping pillow, a corn maze, haunted barn, apple sling shots, pumpkin bowling, and so much more.

Just check out the epic map below of everything you can find!

Located: 251 Powerline Rd, Brantford

9. Brooks Farms

The highlight of Brooks Farms’ season is their Fall Fun Festival! For over a decade, they’ve hosted an awesome fall fest that gets bigger and better every year. Happening until October 31st.

The only thing we love more than exploring their seasonal activations, riding tire horse swings, zip lining, and wagon rides is fall eats! Check out the Hungry Hut Poutine Food Truck, home made donuts, Peameal bacon on a bun, pizza buns, seasonal soups and so much more. Yum!

Loacted: 122 Ashworth Road, Mount Albert


1. Konzelmann Estate Winery

Enjoy Fall Flights at this winery! Cozy up by a private fire with your date and enjoy a seasonal wine flight including their new Pumpkin Spiced Mulled Wine, plus take home your own ingredients for at-home date night mulling. Book your spot online.

Located: 1096 Lakeshore Road, Niagara-on-the-Lake

2. Back 10 Cellars

If you were lucky enough to visit this winery during the summer, you would have been lounging at their Smitten Summerhouse. Now, you can chill outside with all-new Sparkling Smitten Fritter cocktails. Find them on Saturdays and Sundays at the winery. And yes, that’s an apple fritter on top!

Located: 4101 King Street, Beamsville

3. Ravine Vineyard

This winery has a farmhouse feel that already gives fall vibes, and now you can find new donuts in their retail store perfect for the season to finish off a wine tasting. Try their Spiced Pear and Pumpkin Cruller this October!

Located: 1366 York Rd, St. Davids

4. The Hare Wine Co.

Walking through the stone archways and giant gates, you’ll see a completely decked out and transformed winery for the fall season to check out with your date. Inside, you can discover their Pumpkin Spice Wine Cocktails! Stop by the patio on weekends and sip on a Pumpkin Slushy infused with Chardonnay, pumpkin spice, and a hint of Icewine or a twist on the classic Old Fashioned. A Cabernet Franc base mixed with @kvasfbco Northern Maple Old Fashioned Simple Syrup, a zest of fresh orange, garnished with a cinnamon stick. Both sure to warm you up on a crisp Fall day.

Located: 769 Niagara Stone Road, Niagara on the Lake

5. Lakeview Wine Co.

Ever wondered what the best wine to pair with Halloween candy is? At Lakeview, you can find out! Book their Hallowine Tastings every weekend in October you can taste wine paired with classic Halloween candy.

You can also check out Spooky Movie Trivia Night on October 20th at the winery!

Located: 1067 Niagara Stone Rd., Niagara-on-the-Lake


1. Euro Desserts

This pick up-only bakery has gone viral a few times for their inventive treats that taste as good as they look! Having an at-home date night or heading to a get together and in charge of the desserts? Impress with their fall-themed donuts, cannolis, and cakes.

Located: 90 Turbine Dr. #16, North York

2. Lamanna’s Bakery

This is not for the ordinary. The pizzas and desserts that come out of Lamanna’s Bakery are iconic and unique, making them a staple for that Instarammable bucket list foodie date item. For fall, they’re serving up Pumpkin Pie Whoopie Pies, seasonal donuts and gelato flavours, and really anything your date can possibly desire! How about a huge pizza slice covered in pumpkin pie slices? They can do that!

Located: 6758 Kingston Rd, Toronto

3. Nani’s Gelato

A new season means new gelato flavours! Nani’s is already known for having the most creative and gourmet gelato flavours on their ever-changing menu, so it’s only fitting they release some new treats for the fall. This season, find Apple Crumble, Pumpkin Pie, Vanilla Bean, and Salted Dark Chocolate on the menu.

Located: 6 Charles Street East, Toronto

4. Eva’s Original Chimney Stax

Treat yourself with the infamous donut ice cream cone, with a fall twist. Walk through Port Credit or Bloor West with your date in the crisp fall air, and bundle up so you’re not too cold to try a Pecan Pie, Cinnamon Bun Caramel Cheesecake, Pumpkin Pie, or Apple Pie Chimney Stax!

Located: 454 Bloor West, Toronto & 53 Lakeshore East, Port Credit & Square One Shopping Centre, Mississauga

5. Bloomer’s

Bloomer’s is known for their handcrafted vegan donuts, so you know they’d come swinging when the fall season arrived. Get a box of donuts with your date and see which one you like the best; for a fun added date idea, keep polaroid pictures and ratings of the flavours for a cute keepsake. New flavours include Canadian Maple, Apple Pie, Crème Brûlée, Carrot Cake, Pumpkin Pie, and Pecan Butter Tart.

6. Pandoughra’s Cookies & Ice Cream

Inside the Stackt Market is this cute spot for cookies, cookie dough, and ice cream. Always on trend, they have some cute selections for spooky season including Frozen Hot Cocoa, Pumpkin Pie Cookie Dough, Spiked Hazelnut Latte, and even a Halloween Spook Box to get in the spirit!

Located: 28 Bathurst Street #3-122, Toronto

Looking for more date ideas? Click here!

Subscribe to receive our weekly newsletter

Your destination for date ideas and experiences across Canada

Articles, Giveaways, Gift Ideas & More