Ranking Kingston’s best milkshakes

Lifestyle editors and milkshake experts review the city’s best

Ally and Josh are self-proclaimed milkshake experts.

Ally’s Twitter bio lists milkshakes as her number one life pillar. Josh has a self-made poster of a Gold Medal Ribbon milkshake from Baskin Robbins hanging in his bedroom. It didn’t take long for them to come together and search for the best shakes Kingston has to offer.

Based on three restaurants selected through research and word-of-mouth recommendations, The Journal’s Lifestyle Editors set out to rank Kingston’s best milkshakes.


J: I’m a longtime Tommy’s customer and their food is part of my family at this point, which naturally relegates their milkshakes to supporting character status.

This doesn’t mean Tommy’s milkshakes aren’t great. The flavours are uncomplicated and sweet, the consistency is smooth and easily digestible, and their penchant for giving out the extras from each batch feels like a nice lunch lady slipping you an extra pudding for dessert. 

If this milkshake was a movie performance, it’d be Emily Blunt in The Devil Wears Prada—a solid show that props up the experience. But Blunt still plays second fiddle to Meryl Streep and this milkshake lacks the creativity to seriously compete.

A: Over the past year, I’ve chugged my fair share of Tommy’s milkshakes. The only thing better than gorging on breakfast for dinner is washing it down with one of the restaurant’s chocolate shakes. So, walking into the retro-style diner with Josh, I knew I’d leave happy and in a stage-four food coma.

As always, Tommy’s delivered a creamy, perfectly sweet moment of heaven. Although their shakes are a little on the thin side, it’s easy to tell they’re are made with real fruit as advertised. The diner also gets major bonus points for their classic whipped cream and maraschino cherry combo, even though maraschino cherries are absolutely disgusting.

My favourite part of the trip to Tommy’s was pretending to sip sultrily like Riverdale’s Veronica and Betty. Tommy’s is Kingston’s Pop’s Diner and that’s that. 

Rating: 3.5/5

The Works

J: I’ve had my fair share of milkshakes over the past 20 years, but I’ve never been served a drink in a glass measuring cup. I looked at my server with disbelief as she brought forth the ‘2001 Shake Odyssey,’ a mystifying combination of caramel, peanut butter, and Oreo cookies.

A shake with all three of those components sounds too good to be true and, in the end, it was.

This was one of the most creative milkshakes I’d had, but the sweetness was overwhelming. No matter how they tried to balance the flavours, I felt like my veins were pumped with sugar. I appreciated the drink’s ambition, but its thickness and taste left me exhausted by the end.

A: Before this past Friday, I’d only ever been to The Works on the hunt for a good burger. But since it’s scientific fact that a good burger joint also serves great milkshakes, I was optimistic.

Aside from their exciting presentation, this shake was all the best parts of a Wendy’s Frosty and Dairy Queen soft serve. It was also very thick and extremely sweet, so if you’re not a hardcore sweet tooth—I’m talking sugar on your cornflakes hardcore—beware. 

Rating: 3/5

Harper’s Burger Bar

J: Going into this experience, I’d wanted more creativity from a shake and then immediately ate my words when a guttier option came along. Maybe my mindset set me up for this, but Harper’s milkshake felt like a godsend.

I hesitantly combined french vanilla ice cream with Nutella and Mars Bars, and was delighted with the somehow well-balanced outcome. The consistency was moderately thick, the flavour was sweet but not nauseatingly so, and the addition of a spoon helped me scoop up any leftover Mars Bars pieces.

This milkshake felt like it put in an appropriate amount of effort to be great without trying to do it all, which I appreciated at the end of a not-long-enough journey to find Kingston’s best shake.

A: Although Harper’s was the last location Josh and I visited on our tour of Kingston’s milkshakes, if I’m being honest, I don’t remember much about the shake itself. Since chocolate was off the menu for the day, I had to step out of my comfort zone and choose mint chocolate—new and scary territory for me.  

My hope was that it’d be like sipping on a cold After Eight—it wasn’t. That’s not to say it wasn’t good, but it was just a little icier than I would have expected. I did, however, appreciate the spoon they gave along with it, which made for a fun eating-and-sipping experience.  

Rating: 3.5/5

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