Pickering might not be known for a wild nightlife, but these five spots definitely know how to do happy hour right. From classic favourites like Jack Astor’s and Moxie’s to lively vibes at State & Main, The Social, and Mansion Kitchen + Bar, each place brings something a little different to the table. Some have DJs on the weekends, some have killer menus and specials, but all of them are perfect for unwinding after a long day. And just to be clear—this isn’t a ranked list, they’re all worth checking out.
1. Mansion Kitchen + Bar
📍 1294 Kingston Rd, Pickering
🌐 Website
When:
- Monday to Thursday
What time:
- 9PM until Close
Featured Specials:
Wine Bottles half off every Wednesday ALL DAY
Mansion Kitchen + Bar is a foodie haven with upscale ambiance making it the perfect spot to unwind. Their happy hour menu offers something for everyone including a great selection of wines, beers, bar rails, and even a few special cocktails.
*Their short ribs are our favourite, we just can’t get enough!
2. Moxies
📍 1815 Liverpool Rd, Pickering
🌐 Website
When:
- Everyday, Monday – Sunday
What time:
- 2 PM- 5 PM, 9 PM until Close
Featured Specials:
Monday
- CocoRita 1oz | $2 off
- Corona 330ml | $2 off
Tuesday
- Old Fashioned 2oz | $2 off
- Smoked Old Fashioned 2oz | $2 off
Wednesday
- Bottles of Wine 750ml | ½ price
Thursday
- Local Craft Draft 16oz | $2 off
- Sangria 3.5oz | $2 off
Friday
- Tequila Shots 1oz | ½ price
- G & T 2oz | $2 off
Saturday
- Moxies Mule 2oz | $2 off
- Jalapeno Margarita 2oz | $2 off
Sunday
- Mimosa 3oz | $5 off
- Caesar 1oz | $6
Looking for the perfect place to unwind? Moxies has you covered with an amazing lineup of cocktails, brews, wines, and highballs — plus some of their most-loved food items to snack, share, or savour all to yourself. They also have a daily drink features that change every day of the week!
*We love the cozy vibes of their outdoor fire pit and the fish tacos are our fav!
3. Jack Astors:
📍1355 Kingston Rd Unit #9001
🌐Website
When:
- Everyday! Monday – Sunday
What time:
- 2 PM – 5 PM , 9 PM until Close
Featured Specials:
Wine Bottles half off every Tuesday ALL DAY
Jack Astors has a happy hour menu called Five for $5, featuring five different categories of drinks with over 15 different drinks options starting at only $5. From classic cocktails to refreshing pints and everything in between, there’s something for every vibe. Don’t miss their party starters shot menu that has all sorts of fun shots. Grab your friends for a round of Shot Roulette or test your skills with the legendary Slap-Shot-Ski — because why not make it a night to remember?
4. The Social
📍2460 Brock Rd Unit: B8, Pickering
🌐Website
When:
- Monday – Friday
What time:
- 2 PM – 5 PM , 9:30 PM until Close
Featured Specials:
Monday – Friday 16oz Domestic for $6
Monday:
- All day happy hour!
Tuesday:
- Wings & Fries – $12
Wednesday:
- 1lb Wings & 16oz domestic beer – $16
Thursday:
- Wings, Ribs & Fries – $22
The Social is the place to be for tasty apps, cheap beers, and daily specials. With 18 different wing sauces to choose from, there’s a flavour for everybody – best served alongside a cold beer. If beer isn’t your style, their happy hour menu also features wine, espresso martinis, and a variety of other cocktails. This is a great spot to socialize, chow down on some good eats, and wash it back with a delicious drink.
*Shoutout to their nachos (which aren’t on their happy hour menu) – ranking one of the best we’ve had…like EVER!
5. State and Main
📍1355 Kingston Rd Unit 510, Pickering
🌐Website
When:
- Every day
What time:
- 2 PM – 5 PM , 9 PM – Close
Featured Specials:
Monday:
- Mexican Lager 50cl $1 off
- Margaritas 2oz $2 off
Tuesday:
- Mill St Draft 16oz $1 off
Wednesday:
- Wings ½ price | Lawn Mower Yard Draft 16oz $1 off
Thursday:
- Wine 5oz|8oz $1 off | Bottle of Wine ½ price | By the Bottle Only Wines 25%
Saturday:
- White Sangria 3.5oz $2 off
Sunday:
- Signature Caesars 2oz $2 off
State and Main not only has happy hour specials every single day, but they also feature a unique daily special (excluding Fridays) to keep things interesting. Their happy hour menu includes some of their most popular appetizers and mains — don’t miss out on the Baja Fish Tacos or the Chili Coconut Calamari, they’re both local favourites.
Whichever spot you end up at, you’re in for great drinks, tasty bites, and a fun vibe that makes happy hour worth it!
