Don’t you love that feeling when you’re out and about downtown maybe running errands or on your way to meet a friend, headphones cranked to the max, and an absolute banger of a song pops up on your playlist? Sometimes a song perfectly captures the mood you’re in. Or seems to magically intuit where you are, or what you were just thinking about. We want to help you make that magic moment happen when you’re visiting Old Town Toronto; so we’ve made you a mix tape. Check out our selections below and add our Spotify playlist to enjoy next time you’re in the hood.

Diamond Dogs, Artist: David Bowie 

Where to listen: Honestly, you could listen to the entire Diamond Dogs album while strutting around Old Town Toronto in your tallest heels and tightest jeans and have an excellent time, but the eponymous song from Bowie’s 8th studio album is a delight to listen to on your next visit to the Berczy Park Dog Fountain. 

Diamond Dogs not your speed? May we also recommend:

Dog Days are Over, Florence + the Machine

Werewolves of London, Warren Zevon

Dog Days of Summer, Steve Conte

Take on Me, Artist: a-ha

Where to listen: This Norwegian synth-pop hit from 1985 has one of the most iconic music videos of all time. It’s an energetic bop with an emotional charge that’s sure to pump you up on your way to your next Climber Conditioning or Interval Running class at Altitude Fitness- a studio that specializes in preparing you for your next adventure.

May we also recommend:

Under Pressure, Queen/David Bowie

Cherry Bomb, The Runaways

Running Up That Hill, Kate Bush

Take Me To Church, Artist: Hozier

Where to listen:  Okay. Listen. This might be a bit on the nose, but the debut single from the (now) uber-famous singer-songwriter makes for beautifully-moody accompaniment as you appreciate the glow of the newly installed lights in St. James Cathedral. Yes, we know the song is a metaphor and not actually about going to church, but the soul and gospel infusion of this alt-rock tune hits hard whether secular or sacred.  

May we also recommend:

Imagine, John Lennon

Dear Wormwood, The Oh Hellos

Hallelujah, Pentatonix

I Think I Like When it Rains, Artist: WILLIS

cc lounge

Where to listen: If you’re in a dreamy, romantic kind of mood there’s nothing quite like wandering around in a gentle rain with this bluesy WILLIS tune playing. Once you’re ready to dry off try popping into CC Lounge for their famous Toronto cocktail- a twist on a classic Old Fashioned.

May we also recommend:

Barstool, Gary Jules

Helplessness Blues, Fleet Foxes

Nothing’s Gunna hurt You Baby, Cigarettes After Sex

All Too Well (Taylor’s Version), Artist: Taylor Swift

Where to listen: If you haven’t heard the ten-minute, heartwrenching ballad that made the internet cancel Jake Gyllenhaal where have you been? This bittersweet but ultimately uplifting folk tune is best suited to accompany a meandering walk along Market Street and the Esplanade, maybe picking up some seasonal flowers for yourself at the St. Lawrence Farmer’s Market, then sitting down with a hot cocoa at Balzac’s to write in your journal. 

May we also recommend:

Scarborough Fair/Canticle, Simon and Garfunkel 

A Tiskit A Tasket, Ella Fitzgerald

These Boots Are Made For Walkin’, Nancy Sinatra

The Distance, Artist: Cake

Where to listen: If you’re working against a deadline this 90s alt-rock track by Cake is the perfect song to give you a jolt of adrenaline to get you there- especially if you pair it with a snug pair of noise-canceling headphones, a comfy nook, and a double-Americano over ice from Fahrenheit Coffee. 

May we also recommend:

Cosmic Dancer, T. Rex

Where is My Mind?, Pixies

Eleanor Rigby, The Beatles 


So there you have it- a complete playlist for a full day bopping around OTT. Have any songs that remind you of Old Town Toronto you’d like us to add to the playlist? Message us on Instagram and let us know!

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