I’m obsessed with Craig’s Cookies. Mainly because the cookies are seriously the best I’ve ever had—they’re unlike anything in this world. Buttery, but not too buttery. Sweet but not too sweet. Chunky but soft on the inside so that every bite is the perfect bite. It’s the kind of cookie that makes even non-dessert lovers reach for more.
But it’s more than that. It’s because in 2015, before Craig’s Cookies was selling millions of dollars worth of cookies or had six locations, it was just Craig, on his bike, delivering cookies to my front door. He’d take orders on his website or through Facebook groups, and then deliver the cookies the next day. Even then he had wild flavors—Oreo stuffed cookies and Strawberry Pop Tart to name a few. That might not sound that crazy now but in 2015, he was the only person doing flavors like that. It was fun and original. You paid via Paypal in those days and emailed in your order. It was very bootstrapped and very endearing.
I remember the first order I made after finding his website in a Google search for cookie delivery in Toronto. I sent Craig a frantic email that probably made very little sense about how I was in Boston but my boyfriend was in Toronto and could he please leave the cookies behind an old recycling bin in the apartment complex’s hall. The cookies were supposed to be a surprise.
Craig was kind, and understanding, and even sent me a photo after they were delivered, showing a brown bag labeled “Craig’s Cookies :)” with a little smiley. They were tucked safely behind the recycle bin, just as I’d asked. It was the brown bag I’d come to look forward to most as I continued ordering them over the years.
Eventually, I’d introduce these cookies to my mom in New Hampshire (who still begs me to bring several dozen home to Boston every time I’m in Toronto), my friends, and everyone in and around Toronto. Apparently, I wasn’t the only one because by 2018 Craig had opened his first brick-and-mortar in Parkdale with just one employee. He even designed the store to feel like you were going into a loved one’s home, like his grandmother’s house in St John’s, Newfoundland. Before long, the rest of the locations (and 80+ employees) followed.
I guess the reason I love Craig’s Cookies so much isn’t just because the cookies are phenomenal. (which they are. They really are). It’s because this is one of those rare success stories where someone who has a passion, a talent, and a little bit of luck really does get the success they deserve. I guess I also feel a little proud to be one of those OGs that used to get the hand-delivered cookies in the brown bag. To see everything it evolved from, and everything Craig’s success has been able to do for the community.
So if you’re in Toronto, or you have a friend heading that way, ask them to bring you back a dozen or so cookies. It’s hands down the best cookie you’ll ever have and if you’re wondering, yes, they do freeze wonderfully. That’s assuming you have the self-control to not gobble them up.
