Trivia Night in Oakville: Free Entry, Prizes, and The Best Tuesday Night Out on Kerr Street

Tuesday Night’s Best Kept Secret

How many Tuesdays have slipped by in a blur of binge-watching and scrolling until you’re bored with your own feed? If you’ve been craving something fun, social, and actually worth leaving the house for, The Boot Social Pizzeria might just have your new favourite ritual. 

Every other Tuesday, the lights warm up on Kerr Street, the tables fill a little faster, and the room buzzes up; that’s when The Boot, the best Italian restaurant in Oakville, kicks off the Trivia Night. A midweek mix of laughs, friendly competition, and just the right amount of chaos. Hosted by the Black Sheep Entertainment (@blacksheepgta), the games move smoothly, the questions are clever, and the whole night feels like a group hangout disguised as a trivia showdown.

And the best part? It’s completely free. No entry fee. No pressure. Just show up, grab your team (or join one), order something delicious, and settle in for a few rounds of brain-flexing fun.

Trivia Night Oakville - What, When & Where

There’s trivia… and then there’s trivia run by people who actually know how to make a room come alive. At The Boot Social Pizzeria, the magic comes from teaming up with Black Sheep Entertainment, the Greater Toronto Area (GTA) crew famous for turning ordinary quiz nights into full-on experiences. 

Their hosts are sharp, funny, and fast on their feet, keeping the energy high in the room. No awkward pauses, no confusing rules, no “uh… let me double-check the answer” moments. Just a well-run, well-loved game night from start to finish.

The details are simple: Trivia happens every other Tuesday at The Boot, with the action kicking off right at 7:00 PM. And yes, the part everyone loves: Entry is absolutely free.

Book Your Spot for Trivia Night – Click to Reserve!

Fuel Up with the Fun: Pizza, Pints & Tuesday Specials That Fit the Mood

People usually start rolling in to the Free Entry Trivia in Oakville early. Grabbing their favourite table, ordering a thin-crust Italian pizza, and warming up their “team captain voice.” But once the first question hits the mic, the room locks in. Teams huddle. Someone whispers the wrong answer with way too much confidence. It’s all part of the fun.

But trivia nights hit different when the food is actually worth talking about. At The Boot, the menu is practically built for game night. The Boot’s signature thin-crust, Neapolitan-style pizzas come out of the traditional wood-oven blistered, airy, and full of flavour, the kind of “brain fuel” every team secretly believes gives them an edge.

And then there’s the bar. Think ice-cold craft beer, refreshing cocktails, and a lineup of Italian wines that taste even better when your team nails a tough round. If Tuesday specials are running, you’ll usually hear someone whisper, “We should’ve ordered two,” halfway through the first drink.

Conclusion: Your Next Tuesday Night Is Calling

The Boot Social Pizzeria — it’s not a pub pretending to be an Italian spot, or an Italian restaurant pretending to be a trivia venue. It’s both, effortlessly. And on a Tuesday night, that mix is unbeatable.

With free entry, real prizes, amazing food, and a room full of people who just want to have a genuinely fun night out, a Free Entry Trivia Tuesday Night at Kerr Street suddenly feels like the place to be. But fair warning: tables fill fast. The teams get bigger every week. And the regulars? They show up early to claim the best seats, order their favourite pizza, and get an early lead on bragging rights. 

So, reserve your spot, grab your team, be ready to yell “We knew that one!” more than once, and make this Tuesday a night worth remembering. The Boot Social Pizzeria is waiting — with good food and great energy throughout the night.