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The Whippoorwill Restaurant and Tavern – Kitsch and Comfort in Bloordale

June 24, 2014

For the second installment of our office supper club, I decided to once again choose from my long bucket list of restaurants in Toronto. My colleague is friends with the co-owner of The Whippoorwill Restaurant and Tavern (1285 Bloor St. W), Shawn Creamer (also owns the Dakota Tavern), and he had told me marvelous things about their food. Bonus points go to Shawn for also being a member of the awesome local band The Beauties! Along with co-owner and chef Tyler Cunningham, The Whippoorwill has become a dining destination for both locals to the neighbourhood and beyond. The menu presents an array of mouth-watering choices, that made it hard for our large party to settle on any one single item. On top of that they had so many specials for the day that sounded amazing, making ordering even tougher. I knew that NOW Magazine named their burger the best over $10 in 2013 (Winner of Best New Restaurant as well), so that was a strong contender, but everything sounded very delicious and unique. Immediately upon walking in to the restaurant, we felt at home in the retro-kitschy dining room. The bar along the wall presented like an old school diner, and there were so many things to look at, I was in heaven. Our server was also amazing! She had a ton of insight into the various drinks and menu items, and was also extremely helpful in the serious debates many of us were having over what to order. I know that I will be back to try the rest of the menu very soon!

What I drank:


Hemingway’s Mistress ($8): This was one of the special cocktails for the night playing on the theme from a tiki party they had a few nights before. It was made of anejo rum, pisco, maraschino, grapefruit, passion fruit, lemon, and strawberries. Great boozy cocktail in an awesome glass!

What I ate:


Oysters ($3 each): I love oysters and these were perfect! The pickled chilies added a nice hit of spice to accompany the horseradish. I wish I knew it was oyster happy hour (ended up being $7 for three), because I would have ordered a ton more!


Corn ($5): This was one of their special sides for the day. A few of my colleagues ordered it and it seemed to be a hit!


Champs ($5): Another $5 special, I originally thought this was a mushroom dish according to the name, but I was pleasantly surprised to find out it was mashed potatoes topped with cheese and spinach. Mashed potatoes are one of my favourite foods and with the added bonus of cheese, this was the perfect comfort food.


Rainbow Trout ($24): After much struggle and debate I settled on the trout. The combination of ingredients and flavours sounded too good to pass up. The fish was accompanied by wild ginger dashi, asparagus tempura, shiitake mushrooms, and watercress in a seaweed broth. The fish melted in your mouth and was extremely flavourful. I loved the mushrooms and asparagus for texture, and the watercress for a hint of bitterness. The broth was very smoky, which made for a unique taste!


The Whippoorwill Burger ($14): I was so tempted to order this after my colleague said it was the best burger he had ever had, however I was coming off the indulgences of Bonnaroo, and had planned a detox (has not panned out yet). I knew I could probably snag a bite or two off one of the many burgers on the table, so I felt a bit better about choosing the trout. My colleague was nice enough to cut me a sizeable chunk and after biting in, I knew why Shawn had told me the burger was dreamy. The ground prime beef burger was so tender and juicy, and all the accompaniments worked perfectly in each bite. I loved the punch of the Russian dressing, and perfectly melted cheddar cheese especially. It is definitely a messy one, yet in the most incredible way!






The Golden Rule: This was such a perfect choice for our supper club, with a wide range of dishes and drinks, in such a comforting atmosphere. The food was amazing and the service even better! The plating was such a treat for the eye, and the hodge podge of dishware fit the restaurant aesthetic perfectly. I recommend going with a group so you can get a taste of multiple things off the menu. I promise that you will want to once you read it! I love how they have a lot of choice including chalkboard specials, although that can be a problem when you want to eat everything. Definitely will be back to try many more things (and eat a whole burger)!

The Golden Scale: 9/10!

Twitter: @WhippoorwillTO

Instagram: whippoorwillto

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