Taylor Swift is already taking Toronto by storm, and her crew hasn’t even landed in the city yet! Ahead of the pop superstar’s six stadium concert nights spanning from November 14 to November 23rd, 2024 we’re getting in the Swiftie spirit by brainstorming all the best Era’s-coded date ideas to check out in and around Toronto.
So, I’ve teamed up with the amazing team at TSwiftDancePartyCA (shout out to Miri and Victoria!) to create the best list of all the date ideas and spots around Toronto that match the vibe of Taylor’s albums and eras.
So, leave the work to us and dress accordingly for these perfectly themed dates!
Debut
Without Taylor’s Version of her debut self-titled album, we’re going off the vibes and aesthetic of the original 2006 album (but don’t worry, we’re still clowning for the TV release any chance we get). For this, you want to look for unmistakably 2000’s country music and vibes; from the curls to the boots to the southern drawl and everything in between.
Miri and Victoria of TSwiftDancePartyCA recommend hitting up Paris, Texas (461 King St W) for a night out in your favourite denim fits, or attending Open Mic Night at the Free Times Cafe (320 College St).
You can even get nostalgic and tap into your high school party days while line-dancing at Rock N’ Horse Saloon (250 Adelaide St W).
Fearless
Toronto has some magical places for all the golden fairytale vibes of Fearless to explore. One of the most quintessentially Fearless spots in Toronto has to be Casa Loma. From doing a walking tour of the inside, to dinner in the Casa Loma Gardens you’ll feel right inside a Romeo and Juliet story (minus the harrowing end, though, of course).
Miri and Victoria of TSwiftDancePartyCA: recommend booking a dinner & tournament seat at Medieval Times and being whisked away to another universe full of white horses, knights, and castle vibes galore.
Speak Now
Long live date nights! We’re getting into all things purple, sparkling, and ‘girly’. For a Speak Now-coded staycation, head to the St. Regis Toronto with tones of purple among their silvery grey throughout the rooms and gorgeous spa.
Toronto has so many charity galas throughout the year that you can buy tickets to and attend (amazing idea by Miri and Vic)! Head to Fitzroy to try on and rent the most gorgeous, flowy, tulle-y gown and check out the motionball Gala when it comes to town next. This night is truly sparkling.
Miri and Victoria: Butterflies play a huge role in this album vibe as well, so you can head for a date to the Butterfly Conservatory in Cambridge or Niagara Falls donned in your best purples.
Red
Okay we’re well aware there’s a couple different vibes of the Red, so we’ll try to hit both (with a heavy preference on Taylor’s Version of course).
The perfect vibe to hit the fall, muted tones of Red (Taylor’s Version) is hitting up one of Toronto’s fall fairs or apple picking at orchards in the GTA. It’s the perfect album to listen to while singing in the car, getting lost upstate watching the leaves change during autumn. Pull out those red scarves, cozy sweaters and Swift’s signature chai cookies to sit back and enjoy the serenity of fall.
To get a pop of the bright, iconic colour in your downtown Toronto date night, we recommend checking out the Muse Lobby Bar at the all-new Revery Toronto Downtown, Curio Collection by Hilton, it’s seriously gorgeous.
Miri and Victoria: Think a Scarf Knitting Workshop (found at The Knit Cafe on Dundas West), road trip to check out the fall foliage in Ontario, a visit to Her Father’s Cider Bar & Kitchen, or as simple as getting a hot apple cider at Balzac’s and walk about the Distillery District in your favourite peacoat.
1989
For this era, we’re thinking of all date ideas that give you a Welcome To New York vibe in the middle of Toronto. This album had some of the biggest radio singles and music videos that even non-swifties know about, so we want these spots to give the ultimate main character energy.
Get those classic downtown city vibes at a lively bar like the new GRETA Bar YYZ on King Street West, sipping a cocktail to DJ beats at the rooftop of Lavelle, or get artsy at The Drake Hotel’s Sky Yard rooftop bar.
Miri and Victoria of TSwiftDancePartyCA second the Drake Hotel idea, it gives such perfect city vibes and add on the east end’s Broadview Hotel rooftop, and 1 Hotel Toronto’s rooftop bar, Harriet’s to the list as well.
Reputation
If we publish this article, will it make Rep TV come sooner? If you’ve been clowning for the ‘most metal’ era of TayTay’s career like us, we understand that you may need to get your fill elsewhere.
In Toronto, The Bisha Hotel gives the perfect dark vibes in their entrance, lobby, and Mister C. bar for a Reputation-themed night out. During the concert time in November, the whole hotel will actually be transformed into Taylor’s Lover House with each floor representing a different album! We can’t wait to see this.
Plus, The Bisha Hotel now has a Taylor Swift-inspired Suite literally called The Taylor, so how on brand is that?!
Or, get out of the city and stay at this VERY Reputation-coded room at Hotel Philco in Crystal Beach, ON. Check out their Black Room, where everything is black, you even think the photos are taken in greyscale!
Miri and Victoria: Get “dive bar on the east side where you at??” vibes at Goods & Provisions and The Comrade, quite literally, both located on Queen E. in Leslieville; or go for the dark Reputation vibes at Bar Mordecai.
Lover
We’re thinking bubblegum pink and cotton candy clouds, glittery hearts, and being in love. Possibly one of the most datenight-y eras, we’re living in pastels writing this paragraph.
Head to Sugar Beach for those bubblegum pink beach vibes, while still being very much in the *big city*, or Le Tigre Cocktail Bar for a date at the pink-est bar in all of Toronto.
Also, the cotton candy-clad ice cream shop Dutch Dreams gives us such Lover vibes for a cute summer date!
Okay hear us out on this vibe shift, all inspired by her life and time in London that obviously really kicked in during this era. I know it’s so joe-over (sorry, no puns for Matty), but if you want to recreate the London Boy vibes of Lover, head to Bar Wellington or Compton Ave inspired by the city. We still hope it’s shitty in The Black Dog, though.
Miri and Victoria: Brunch at Oretta (honestly, King West and Midtown both work here) or a classier Champagne and oysters date at C.O.C.
folklore
As Taylor Swift said herself, you have to envision yourself listening to folklore like you’re a Victorian lady with a candle stick wandering through the woods and writing poetry in a cottage. Naturally, we have to tap into our ‘middle of a forest cabin’ vibes in a huge, loud, bustling, always busy city… but there’s some spots that make it work!
On Queen West, Cafe 23 is a beautiful, rustic cafe with a hidden vine-y back patio, and the perfect place to write in your journal, or write letters to a long lost love.
Wandering into the Elgin & Winter Garden Theatre to see one of their stage productions will actually make you feel like you’re stepping into the album cover with its wintery yet lush foliage.
Miri and Victoria: Stroll through the Allan Gardens, have a picnic on a secluded spot of the Toronto Islands or in High Park, or go on a self-guided walking tour of Toronto’s ravines.
evermore
Sing life was a willow and it bend right to your wind while sitting under one of the most majestic Willow trees we’ve ever seen, while staying at the Willow Farmhouse in Niagara-on-the-Lake, a woodsy (and possibly haunted) small town. If that sentence doesn’t scream evermore we don’t know what does! Book a stay here.
Miri and Victoria: Evangeline (careful, you may haunt a corner at this vibey Toronto bar); another option is heading to St. Lawrence Market to shop for dinner groceries (or Chai cookie ingredients) then home to cook and drink (white) wine (plaid coat optional).
Midnights
For this bedazzled, nostalgic nightlife/70s indie album (did we get the aesthetic right?) blending all of Taylor Swift’s album vibes and eras, we recommend some hazy, dazzling, and artsy spots around Toronto.
We’ve got KISSA, a Japanese-style vinyl listening lounge and 915 Dupont, a chill spot that’s a hi-fi listening bar by night, café by day and resto-lounge a few evenings a week. Both of these are giving alternate vinyl album covers Midnights, with all the retro vibes.
We’re so thankful Midnights has so many different vibes and aesthetics to it, because you can go from the depths of nostalgic nights to getting in the Lavender Haze, shall we say, and heading to one of the GTA’s gorgeous lavender fields (see: Purple Hills Lavender Farm) – all while staying on-theme!
Miri and Victoria: Experience Toronto Midnights style at ROM After Dark, a curious and seriously vibey date idea that’s diary-worthy.
TTPD
Okay dark academia, we see you! Toronto not only matches this vibe by having greige, cloudy and cool conditions most of the year but we also have some seriously vibey spots for all the tortured poets, writers, writers-blocked, and Lovelorn.
Try grabbing a drink at Library Bar at the Fairmont Royal York or Writer’s Room Bar at Toronto’s Park Hyatt hotel, or even Prequel & Co. Apothecary. Bring a notebook and pen poetic phrases to each other as you get inspired by your surroundings.
Did you really beam me up? To tap into the extra-terrestrial (yet dazzling) side of TTPD, check out Offworld Bar on Queen Street West that’ll have us in love for a fortnight.
We’re keeping an eye on all things Taylor Swift Era’s tour ahead of November, stay tuned here for the best swiftie date ideas.
