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Where to have fun in Oakville after 8:00 pm

Anyone who lives in the GTA has heard plenty about the things to do in Toronto or Niagara, which are great for tourists, but not many know the hidden gems that don’t require a Go Train ticket. 

Oakville is much more than million-dollar houses and sports cars, what this town offers is a destination to unwind; the lakefront at sunset will invoke feelings of nostalgia, a quick drive down lake shore will make you want to chase your wildest career aspirations, and a visit to any local bakery will treat you to some of the best brews and baked goods in the region.

However, people need to know that these streets don’t roll up after 8 pm, so if you’ve got a little bit more energy after picnics by the lake and applying for an MBA here are 5 spots in Oakville that are perfect for rejuvenating and unwinding:

First, let’s set the scene, it’s a Friday evening - you’re coming off a long week of work, your phone is blowing up with messages… Everyone is looking to get out on the town tonight, what are you suggesting?

1. The Kings Arms (323 Church St)

Kings Arms | Rick Brown
Kings Arms | Rick Brown

A great spot and a local favorite that can have you enjoying a delicious dinner at 8, shooting pool by 9, and laughing with friends over drinks up until 2 in the morning if you wish. Located in the heart of downtown Oakville and most notorious for its lively atmosphere, off-the-charts quality of food and drinks, and friendly staff.

The Kings Arms is a one-stop shop where you can enjoy live music, games on the big screen, karaoke nights, or celebrate an occasion over some top-notch food and drinks. It’s got that energy that you could only find from a local spot that has been a staple in the community for years attracting a diverse crowd of locals and visitors alike.

So whether you’re looking for a nice dinner in the evening, to save the cost of an admissions fee at a nightclub in Toronto, or you and your friends are night owls unwinding from a long week, the Kings Arms has you covered.

So let's say you hit the Kings Arms on Friday, wake up a little later on Saturday - but tonight you’re feeling a completely new vibe. You want a place to relax, catch live entertainment, and enjoy some light food with delicious drinks, where do you go?

2. The Moonshine Cafe (137 Kerr St)

Moonshine Cafe | Rick Brown
Moonshine Cafe | Rick Brown

As an Oakville nightlife right of passage, you and your friends have to check out the vibrant music scene at The Moonshine Cafe. Live music every single night and not just cover songs, home-bred original music and tremendous talent all night long. It's a must-visit destination not only for music enthusiasts but anyone seeking a unique and entertaining experience.

For nearly 2 decades they’ve provided a great venue for local talent to be able to showcase what they love to do and put on a show that will truly be a memorable and great night out for locals. Also, not to mention, they’ve got a great menu of BBQ’d sandwiches.

So now let’s say maybe you’ve got some people coming into town tonight. You show them the waterfront, head over to the Nike Factory in Burloak for a shopping trip. You run a bit longer than expected and everybody’s looking for a place to eat close by… What do you do?

3. BLK Swan (3420 Rebecca St)

Rick Brown
Rick Brown

When it comes to atmosphere, quality food, and charismatic staff, it doesn’t get much better than BLK. With a seemingly endless variety of drinks and even a secret late night food menu, it’s the ultimate destination for an unforgettable dining experience.

It’s a great place to relax, eat good food, have good drinks, Karaoke, and if you happen to drop by between May 20th-22nd, you’ll catch live music to celebrate the opening of PATIO SEASON!

Unwinding and enjoying yourself is the name of the game when it comes to nights out in Oakville and BLK is one of the newest, hottest spots to uphold this reputation.

So you have a great night at BLK Swan but there’s a game on in 30 minutes and everyone wants to watch but they don’t just want to sit down... Where do you go?

4. Monaghans (1289 Marlborough Ct)

Monaghans | Rick Brown
Monaghans | Rick Brown

A straight shot up Trafalgar and you’ll find yourself at Monaghans, a sports pub with tons of space and billiards as well as TVs to watch the game. Should you come in on a Friday, you’ll catch the Fish and Chip special, come back on Monday and you’ll need a bib because it’s Wing Night!

Since you’re coming in on a Saturday, you’ll be able to catch live music and even have access to a large drink menu (including over 20 different beer labels). Monaghans has one of those atmospheres that just lets you unwind and have a good time. The staff is great, the drinks are cold and the company is always lively.

Alternatively, if you’re someone looking for a more unique and intimate experience, we might know just the place…

5. The Tin Cup (1540 North Service Rd W)

Rick Brown
Rick Brown

The Tin Cup is the perfect spot to visit for sports fans in the GTA. Tucked away in a cozy corner of Oakville, the Tin Cup offers a distinct charm that you simply won’t find anywhere else. The rustic decor, dim lighting, and comfortable seating create a relaxed ambiance that is great to bring friends, watch the game, and really just live in the moment. 

The menu is fantastic, whether you're craving juicy burgers, crispy wings, flavorful nachos, or warm pretzels, their menu has something to please every palate.

Oakville is more than just a community, it’s a lifestyle available to everyone who visits. You’ll find an atmosphere that’s right for you no matter what your interests or preferences may be. Just make sure to explore beyond the surface and dive into the diverse offerings of Oakville.


Ben Brown

About the Author: Ben Brown

Ben Brown is a local news reporter from Oakville, Ontario, a graduate from WIlfrid Laurier University and a self-published author. His main focus is reporting on crime, local businesses and achievements, and general news assignments throughout town
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