Beat The Heat and Muskoka Crowds: A Guide to an Epic August Long Weekend in Oakville

Happy long weekend! The August long weekend is fast approaching and there is no better feeling than getting three days away from the office and your everyday routine. Take full advantage by spending it in Oakville. This four-day itinerary will give you the lowdown on the best places to visit this long weekend.

Day 1- Friday night:

MEDITERRANEAN CUISINE AND JAZZ MUSIC

Start your long weekend by heading to Oakville Friday night. Check into your hotel and visit Downtown Oakville for a delicious dinner. Click here for a list of all the hotels available in Oakville. Downtown Oakville is home to over 30 restaurants with a range of diverse cuisine. We recommend that you try Colossus Greek Tavern. With their authentic Mediterranean cuisine and décor, you’ll feel like you’ve been transported to Greece.

Fun fact: FUBAR, a spy thriller staring Arnold Schwarzenegger recently filmed a scene in Colossus Greek Tavern! For a full list of restaurants in Downtown Oakville visit here.

After dinner, walk around the Downtown streets and window shop the boutique storefronts. Grab yourself a treat at Maverick’s Donuts or Sugar Suite and visit Towne Square at the intersection of George Street and Lakeshore Road.

Starting at 7:00 p.m., Towne Square hosts live jazz music every Friday throughout the summer. Kick off your long weekend by enjoying live music and treating yourself to a sweet treat.

Day 2- Saturday:

EXPLORE OAKVILLE BY LAND AND WATER

Start your morning at the Oakville Farmer’s Market.  At the Farmer’s Market you will find over 40 unique vendors, including home décor, local restaurants showcasing their best dishes, and of course, baked goods and local produce. The Market is open from 8:00 a.m. – 1:30 p.m. every Saturday until the end of November.

Once you have wandered the Farmer’s Market and explored the array of vendors, it’s time to hit the Lake for stand-up paddle boarding. Swing by Paddle Sports Performance to pick up your stand-up paddleboard (SUP). Paddle Sports Performance offers SUP rentals for those who have experience paddle boarding. If you have never paddle boarded before, you are in luck. The facility also offers private lessons for those wanting to learn. Rent your stand-up paddle board or book lessons in advance on their website.

After enjoying your paddle on Lake Ontario it’s time for lunch in Kerr Village with it’s mix of small-town hospitality and urban revitalization, Kerr Village is a destination for niche foodies and hobbyists alike. Stop by Community Restaurant to try their mouth-watering vegan menu.

Once  you’ve enjoyed your lunch, grab a milkshake at Visit Oakville’s Talk of the Town best milkshake winner, La Dolce Vita and take a stroll through Tannery Park. Visit the Tannery Park Becan, Moccasin Identifier, and butterfly garden.

Next, head back to Downtown Oakville and revisit any of the stores that caught your eye last night.  

Once you have finished shopping in Downtown Oakville take a short drive to Gairloch Gardens. This Oakville gem is a breathtaking outdoor oasis next to Lake Ontario. Walk amongst the rose bushes, over the bridge, around the pond, and through the onsite art gallery.

The last stop of the day is Joshua Creek Heritage Art Centre for their Dinner & Stroll with Alpacas event – a perfect family-friendly evening. On August 3, enjoy an outdoor pasta dinner and walk around the grounds with your very own alpaca!

Day 3- Sunday:

A BLAST FROM THE PAST- A DEEPER DIVE INTO OAKVILLE’S HISTORY

Begin the day by learning more about Oakville’s rich history with the Canadian Caribbean Association of Halton and their guided Black History walking tour. Make your way through Kerr Village and learn more about black history in Oakville.

After you have finished your tour take a short drive to Downtown Oakville just in time for lunch. Grab a seat at Verace Restaurant which has won Visit Oakville’s Talk of the Town award for best seafood and was recently named one of the top 100 restaurants for outdoor dining in Canada by OpenTable.

After you have enjoyed your lunch, stay in Downtown Oakville and experience Oakville’s first ever retro roller-skating event.  On August 4, the Downtown Oakville Business Improvement Area is hosting a retro roller jam. Reserve your spot and equipment beforehand here, and spend the afternoon skating and listening to music in Downtown Oakville.  

After you have skated around Oakville, get an even deeper understanding of Oakville by visiting the Oakville Museum. The Oakville Museum is a short walk from the roller jam. Along your way, you will see plaques on historical homes honouring who built the homes and the year they were constructed. Visit the Museum and learn more about Oakville’s black history and the contribution Oakville made to the Royal Canadian Air Force.  

After you have learned more about Oakville, it’s time to cool off with a boat ride. Oakville has three boat charters:

• Charter Ability, which docks out of Downtown Oakville and will take you on a free pleasure cruise up Sixteen Mile Creek.

• Hearn Fishing Charters docks out of Bronte Harbour. You can book Hearn Fishing Charters for fishing and pleasure cruises.

• Osprey Charter Fishing docks out of Bronte Harbour and will take you on a fishing trip for salmon and trout.

Whether you are in the mood for fishing or a pleasure cruise, you will for sure have a memorable time on the water. Please make reservations prior to arriving.

Wrap up the evening with dinner at Bronte Boathouse in Bronte Village.  Enjoy a cocktail and dinner on their patio and soak in the sun and breeze overlooking Bronte Harbour. Reservations are recommended before you arrive. You can make reservations here.

Day 4- Monday:

ENDING YOUR LONG WEEKEND ON A POSITIVE NOTE

Your long weekend may be coming to an end but there is still a lot to see and do!

Grab an early breakfast at Pur and Simple located in the Bronte Village Market Square before heading to Bronte Heritage Waterfront Park for the annual Art in the Park event. The event features more than 175 artists and artisans from across the country. Every medium is represented, from traditional oil, acrylic, and watercolor paintings to glass, ceramics, photography, mixed media, sculptures and fine jewellery.

Continue your visit in Bronte by grabbing an ice cream at Duckies Dairy Bar, Flavour Fox, or Happy Food Hub and exploring Bronte Heritage Waterfront Park and the At Home in Bronte Muskoka chair exhibit. All of the Muskoka chairs in Bronte are hand painted by residents, local artists, and business owners.

Next, head back to the grounds of the Oakville Museum to take part in the Emancipation Day picnic. Bring your lawn chairs and picnic blankets and enjoy music from Kevin Adams & Voices of Praise Choir and family friendly activities presented by entertainer Nick Gordon. The Canadian Caribbean Association of Halton is also giving away 250 free meals during the event. Meals are limited, will be given away on a first come first served basis, and need to be booked in advance. Visit the CCAH’s website to learn more about the event and to pre-register for a meal.

As your long weekend comes to an end take one last moment to treat yourself at Rosewater Spa. This Talk of the Town best spa winner has everything from manicures, facials, and massages. Book an appointment at the spa and let yourself be pampered.

Unable to get a lunch during the Emancipation Day picnic? The Rosewater Spa also offers spa lunches.

As you head back home, grab yourself a baked good at The Sweetest Thing Bakery to enjoy during your car ride. We hope you enjoy your time in Oakville.

Be sure to tag Visit Oakville in your adventures and let us know what the highlight of your long weekend was!

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