Fun Things To Do In Oakville Ontario On A Weekend Getaway

Oakville is a great place to visit for a weekend getaway. There are plenty of fun things to do in Oakville, which is located close to Toronto, making it easy to get to. It’s also a short drive from Burlington and Milton (all three towns are in the Halton Region).

With Black History Month and the Taste of Oakville festival happening at the start of the year, we got to experience all of the best reasons to visit Oakville. And so we decided to put them together for you. Both the Black History Tour and the Black History Exhibit at the Oakville Museum (mentioned later in this post) are available all year while the Taste of Oakville runs roughly from mid-February to mid-March.

Here’s a guide on the best attractions and places to visit in Oakville.

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A History of Oakville

• Oakville, Ontario’s history dates back to 1830 when Colonel William K. Chisholm founded it. 

• The town became an extension of the Underground Railroad, which led escaped African slaves out of America and into Canadian towns. There were also several slaves smuggled out of America and into Oakville by the famous Captain Robert Wilson.

• Certain African American families, after escaping slavery, settled in Oakville and opened up businesses. These people opened up barbers, fruit farms, and other companies. And when the town was incorporated in 1857, it was ready to become the thriving industrial community known today—rated as one of the top five places to live in Canada.

Getting To Oakville From Toronto

Oakville is a 30-minute drive from Toronto, and the town is a short distance from several airports. Here are the best ways to get to Oakville. 

By Bus

There is a ±30-minute bus ride directly from Renforth Dr in Toronto to Trafalgar Rd. @ Hwy. 407 Park & Ride in Oakville. This only gets you to the bus stop, and then you’ll need to find your way to your accommodation. 

By Train

Trains from Toronto to Oakville leave multiple times a day. Direct train routes between the two take 22 minutes to get you to Oakville from Toronto. Train tickets are pretty affordable, ranging from 20 CAD to 25 CAD. 

What To Do in Oakville, Ontario: Weekend Itinerary

Here’s a basic layout of the perfect weekend itinerary and all the best Oakville attractions:

• Arrive in the afternoon – Afternoon hike in Bronte Creek Provincial Park, and then dinner at Chop Steakhouse & Bar.
• Day 1 – Bronte Village, then Kerr Village.
• Day 2 – Downtown Oakville.

Find more information about each stop on the itinerary below.

Bronte Creek Provincial Park

Start your time in Oakville with an afternoon hike. Pick any of the trails below and enjoy a comfortable and stunning walk. These are all located in the Day Use area of the park.

• Maiden’s Blush Trail – a 1-kilometre, wheelchair-accessible paved trail through the forest. 

• Trillium Trail – also wheelchair accessible and stroller-friendly, this 1-kilometre trail offers gorgeous views of the valley floor and spring wildflowers in bloom.
• Ravine Trail – a bit longer, this 2.7-kilometre trail winds around the valley’s top. You’ll walk between Spruce Lane Farm and Lot A’s picnic area.

Chop Steakhouse & Bar

Chop Steakhouse’s menu is stacked with 100% premium Canadian beef steaks, as well as fresh seafood and other hearty meals. The drinks are varied, with specialty coffees, daily featured cocktails, and plenty of ciders and beers on offer. But the must-have here is the proprietary beer, Big Life Amber Ale, made by Creemore. 

• View their Taste of Oakville menu HERE

Day 1 – Oakville Attractions: Discover Bronte Village

Bronte Village began as a small fishing village in 1834, built on the spot where the Twelve Mile Creek met Lake Ontario. The harbour was established in 1894, making it one of the oldest lakeside communities in Ontario. 

This small village also served as an entry point for many African Americans entering Canada through the Underground Railroad system. Some of these individuals chose to build their homes right here, on the shores of the lake. 

Black History Bike Tour

There are many locations and landmarks that remain from when the African Americans landed in Bronte Village. One of the best ways to see these Oakville points of interest is to hop on a bike (if you haven’t bought your own, rent one) and take this self-guided tour. 

Bronte Heritage Waterfront Park

This waterfront park is popular with locals and visitors alike. There is space to take a stroll, chat and sip on a good cup of Oakville coffee (Taste of Columbia is super). There is a playground for the kids and big grassy patches for the canines. 

Muskoka Chair Display

What began in 2017 as a fun community project has become quite popular around town. Bronte BIA’s “At Home in Bronte” initiative (Business Improvement Area) sees organizations and groups of locals come together and paint lounge chairs in specific themes.

If you walk along the Lakeshore, you’ll notice these brightly-coloured chairs. Take a seat for a moment and soak in the views and atmosphere that Bronte Village provides. 

Bronte Village Shopping

A few great businesses to check out while you’re here: 

• EcoFillosophy specializes in eco-friendly products, reusables over disposables, and even has a refill program. 
• Goldwyn & Sons – for a real treat and some essential grooming, Goldwyn & Sons does haircuts, beard trims, and other upscale treatments paired with a drink.

Bronte Village Specialty Foods

Take your tastebuds on a journey at any (or all) of these spots:

• Flavour Fox – a range of flavours, as well as hot drinks and even fro-yo for the dogs.
• Taste of Colombia – find Fair Trade coffee, gifts, savoury and sweet foods, and even coffee cocktails here. 

La Parisienne Crêperie (Temporarly Closed)

La Parisienne Crêperie is a husband-and-wife-run Parisian-style cafe that provids sweet & savoury French-style crêpes. The way the inside is decorated 

La Parisienne Creperie is a little piece of France in Bronte Harbour. Owned by husband-and-wife team Mikael and Courtney Colas, who took over their family business and breathed new energy into the space! The completely renovated interior of the restaurant will instantly take you back to a cute cafe in Paris.

Meanwhile, the delicious sweet & savoury French-style crêpes are delicious and made with fresh, local ingredients whenever possible to support the local farmers and winemakers. 

This place is on its way to no longer being a hidden gem!

• View their Taste of Oakville menu HERE
  

Coronation Park

This park is right on the shores of Lake Ontario and offers plenty of grassy space, volleyball nets, and picnic tables. You can even see the Toronto skyline on a clear day as you look out over Lake Ontario. 

Kerr Village

Today, Kerr Village is a quaint little community comprising boutique shops, hospitable restaurants, and a strong feeling of community. But back in the 1850s, the village was a haven for African Americans fleeing America who built their homes here. 

Self-Guided Black History Tour

An insightful self-guided tour is available to anyone wanting to explore the buildings and places of interest surrounding Kerr Village’s Black History significance. 

Just a few things to take note of from the tour include:

• Burnet Park – In 2019, a plaque commemorated the 40,000+ African American people who migrated to Canada through the Underground Railroad.

• The Adams Home – initially owned by Jeremiah B Adams, was kept in the Adams family for 100+ years. It was demolished in 2016, but you can visit where it stood. 

• Shipyard Park is fast becoming public and a permanent dedication to Oakville’s Black history as its one of the places along Lake Ontario where American slaves first arrived.

• Turner Chapel Antiques and Appraisers – once the Turner African Methodist Episcopal Church, built in 1891 by former slaves. 

• Kerr Street – the original home of the much-loved Carousel of Nations Multicultural Festival, Kerr St. is the heart of this village and holds much of its history.

Tannery Park

Tannery Park offers views of Lake Ontario, public washrooms, and plenty of space for the whole family to relax. On a clear day, you can also see Toronto’s skyline from here.

Some points of interest inside the park:

• Oakville Lighthouse – you can’t go in the actual lighthouse, but the scene from the outside is worth the stop. 
• Waterfront Trail – spanning through Tannery park, you can stroll down this trail and enjoy the fresh air and lakeside views.

Kerr Village Shopping

• Dove + Arrow – stop here to purchase locally-made products as souvenirs and gifts. 
• The Kind Matter Company is another fantastic Oakville eco-friendly shop for zero-waste shopping. 

Kerr Village Specialty Foods

Some of these spots are a part of the Taste of Oakville festival, and others are just worth a visit. 

• Farmhouse Artisan Cheese is a great place to pick up gourmet cheese for a picnic and a few locally-made products. 
• The Sweetest Thing is a boutique bakery with delicious cakes, cookies, and coffee. 
• Vereda Central Coffee Roasters is undoubtedly home to the best coffee in Kerr Village. 
• Café Mix Up – a Black-owned mother-and-son operation serving everything from soup and salad to pasta and desserts.
• Community Restaurant – serving delicious meals with a 100% plant-based menu.

Jac’s Bistro

Jac’s Bistro is a trendy French/Italian restaurant on Kerr Street. It has been voted one of the best restaurants in the GTA by Toronto Life Magazine and Chatelaine Magazine.

The menu features classic dishes from France and Italy, emphasizing fresh ingredients and local products. Jac’s Bistrot offers a wide variety of wines by the glass or bottle as well as specialty cocktails.

• View their Taste of Oakville menu HERE

Film.Ca Cinemas

Independently owned and operated by an Oakville local, this cinema has five screens to show new movies and classic favourites. Their unique aspect, though, is the magnificent snack bar available. 

Day 2 – Head to Downtown Oakville

The heart of Downtown Oakville is a bustling neighbourhood filled with interesting shops, local businesses, and upscale eateries. This is a spectacular part of town with Six Mile Creek running right through Downtown Oakville and Lake Ontario showing off its beauty from the harbour. 

This is where the town’s founder, Colonel William Chisholm, settled in and built his home. And later, it’s where the African-American people would come to develop their businesses and new lives. 

Sixteen Mile Creek

Start the morning at 16 Mile Creek. The main loop trail runs for about 6 kilometres, crossing the creek on both sides, and there are several side trails. There are some sections where there are hills, but the paths aren’t too busy. The trails have fantastic lookout points, where you might see wild animals.

The Moccasin trail is part of Ontario‘s heritage trails, encouraging hikers to explore the landscape from a First Nation perspective. A series of 13 Indigenous plaques tell Indigenous stories and offer a deeper understanding of Indigenous cultures.

If you visit during or after a fresh fall of snow, it’s nothing short of breathtaking.

The Simple Kitchen

The Simple Kitchen is perfect for breakfast, with delicious but healthy options to start the day. It offers a wide range of low-carb, paleo and gluten-free products, including healthy whole foods for takeaways, granolas, beverages, and natural body care products.

View their Taste of Oakville menu HERE

Browse a Few Shops & Businesses

• Burrows Clothiers – if you’re looking for some upscale clothing for men to wear for your evening plans, stop in at Burrows, and they’ll sort you out.
• Village Cigar Company & Barbershop – cigars, sophistication, and gent’s haircuts. We visited the sister company in Burlington and can say you won’t be sorry you stopped in. 
• Maker’s Mojo – a marketplace for uniquely handmade products, perfect for gift shopping. 

Nyla’s Room

You must have lunch at this Black-owned tea room and delight in oven-baked goodness, award-winning gelato, and some comfort food.

Nyla’s Room embraces each customer with its unique Jamaican style. It celebrates some of the world’s best-loved comfort foods from Jamaica’s North Coast. Hospitality. We wouldn’t be surprised if you found it difficult to leave as the staff are incredible, fun and warmly welcoming.

Nyla was inspired by her family’s history and her appreciation for cuisines, and the hospitality she experienced when travelling. Nyla‘s room is a Gelateria/Café meets Teahouse.

View their Taste of Oakville menu HERE

Other Downtown Specialty Foods

• Tribeca Coffee Co. – grab a New York-inspired coffee while you send out an email in this specialty coffee house. 
• Wallflower Doughnuts – located inside Tribeca Coffee, these donuts go perfectly with a cup of coffee or tea.
• Black Forest Pastry Shop – fresh, mouthwatering pastries baked and sold daily.
• Sugar Suite – sweet and savoury baked goods, with gluten-free and vegan options available.

Oakville Towne Square

This is the heart of Downtown, and you’ll find numerous shops and businesses within the square. 

George’s Square

This leafy square is home to the Veteran’s Wall memorials that Oakville put up to remember and honour their war veterans. 

Historic Homes and Churches on Alan and Navy Streets

Alan and Navy Streets are both home to several historic homes and churches. A stroll down each of these streets allows you to view these buildings and perhaps learn even more about this town’s history.

Oakville Museum

When Colonel William Chisholm founded Oakville, he built Erchless Estate in a prime spot – overlooking the harbour and Lake Ontario. This family home is now the Oakville Community Museum. 

The museum displays Oakville’s rich and captivating history with various exhibits. Two of these are centred around Oakville’s Black history. One exhibit shows the story of a freeborn African-American, Branson Johnson and his life in Oakville. And another is a multi-media presentation of a former slave, Debra Brown’s journey in the Underground Railroad. 

Lakeside Park

Lakeside Park is home to Oakville’s first post office and an 1829 residence (The Thomas House). It’s also where you will find the TOWARF Canadian Coast Guard Auxiliary. The park has public restrooms, benches, and endless grassy areas to sit and enjoy the space. 

Dingle Park

Another splendid open space in Oakville, Dingle Park, offers walking paths, picnic benches, and impressive views of Lake Ontario and the Toronto skyline. It’s small but often also peaceful, so it’s a great place just to gather your thoughts and appreciate the scenes around you. 

Oakville Galleries

This space is a not-for-profit contemporary art museum housed in the public library. It is designed to bring communities together in unconventional and unexpected ways. 

One of the must-see exhibits is the Two Truths and a Lie exhibit. It’s a collaborative artistic expression from several artists. This speaks to the “complex interactions within the pursuit of truth.”

The Oakville Centre for the Performing Arts

This centre puts on multiple performances each year, a fantastic place for the Oakville community to unite in dance, music, and storytelling. You can find a schedule and book tickets on their website. 

CAMERON’S Brewing Company

The perfect way to end your Oakville visit, enjoy an ice-cold beer from this award-winning, family-run brewery. There are occasional events here, too, with live music and catered food to accompany what many people say is “the best beer in Canada.”

Glen Abbey Golf Club

The world-famous Glen Abbey Golf Club has been the site of 25 Canadian Open Championships –– most notably when Tiger Woods defeated Grant Waite in 2000. Whether you’re a pro golf enthusiast or just looking for a relaxing brunch spot, the Glen Abbey Golf Club is a great choice. The club is also home to a golf academy for those wishing to learn the art of the sport.

Also located at Glen Abbey Golf Club is the Canadian Golf Hall of Fame, where visitors can learn about the rich golf history in Canada. Notable inductees include Stephen Ames, Michael Weir, Sandra Post, Stanley Thompson, and the legendary Jack Nicklaus.

Where to Stay in Oakville + Map

Along with the engaging stories that Oakville has to tell, the town’s hospitality is another reason to visit. Here’s where we chose to stay in Oakville. 

• Sandman Oakville – a comfy and convenient place to settle in for a night or two in Oakville. 

• Holiday Inn Oakville Centre is located close to Downton for easy travel to the top attractions and landmarks. 

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