Top Things to Do in Oakville This Summer (2025 Guide)

Looking for the best things to do in Oakville, Ontario this summer? Whether you're a local resident or just visiting, we've rounded up 10 of the top summer activities in Oakville for 2025. From live music and art shows to lakeside trails and sweet treats, this guide will help you make the most of the season. We love any opportunity to share reasons to visit our community. 

1.    Wander Oakville’s Waterfront Trail & Watch the Sunrise (or Sunset) from Tannery Park

Start at the bottom of Allan Street and the waterfront trail that follows beautiful shoreline paths, mixed with residential sidewalks. It leads you to the Lakeside Park on the east side of the harbour which offers scenic walking paths, rose gardens, a pier, playgrounds for the kids and sweeping views of Lake Ontario and Toronto across the water. OR start on the west side, find parking at the bottom of Kerr Street, follow the waterfront trail along to Tannery Park. Start your morning strong with a view of the sunrise over Toronto in the distance, from the Tannery Hill Beacon.  

2.    Explore Oakville’s Art Festivals & Galleries

Art in the Park | Bronte Heritage Waterfront Park | August 4th | 10AM – 4PM

In 1965, the OAS created Art in the Park to promote local artists and artisans. Today this show has blossomed into Oakville’s premiere art event with artists and artisans from across the country. This show boasts only original work where artists are chosen for their originality and command of their chosen medium. Every medium is represented, from traditional oil, acrylic, and watercolour paintings, to glass, ceramics, photography, mixed media, sculpture, and fine jewelry.

Art in My Garden | Old Oakville Neighbourhood | September 6th | 12PM – 3PM

Have you checked out the unique experience that is Art In My Garden before? Enjoy a stroll in the picturesque neighbourhood of old Oakville and discover original art from 70 local artists across 35 garden locations. It is a free, non-commercial (no-sales) event in celebration of the creative community - a gift from artists to bring joy to your day. Meet the artists, be inspired by the stories of their work and enjoy being part this celebration of creativity and community.

Gairloch Gardens | 1306 Lakeshore Road East

Oakville Galleries presents the exhibition Between Heaven and Earth, and the Ship of Tolerance, by Ilya & Emilia Kabakov at Oakville’s Gairloch Gardens. Between Heaven and Earth highlights a number of the artists’ works, including paintings, prints and installations, and spills out into the gardens with several larger artworks. The largest installation is The Ship of Tolerance, a 60-foot long, hand-crafted wooden ship with sails made from children’s paintings, which is being presented lakeside in Gairloch Gardens for one year. At the same time be sure to wander through the gorgeous stone pathways and gardens throughout the property.

Art in My Garden, Oakville, previous year

3.    Shop Local in Downtown Oakville

Stroll through Old Oakville, where boutique shopping, lakeside cafes, and harbour views blend with historic architecture. Some of our team’s favourites include:

Home décor & furnishings: FOR, Rainsford Company
Clothing & accessories: Homebody Studio, Anthropologie, Burrows, MUST Boutique
Floral & outdoor: Flower Deco 
Kitchen supplies & grocery: Olives en Folie, Nicety’s

4.    Head Out for a Delicious Cup of Coffee & Pastry to Start the Morning

For our family there is nothing better than wandering into downtown Oakville for a fresh cup of coffee, or tea, to start your morning. Bonus if you have time to grab a pastry or baked good as well!

Wet Coffee – Banana Split Matcha
Tribeca Coffee Co. – Nitro Cold Brew
Peach Coffee Co. – Iced Latte
Black Forest Pastry Shop – Classic Chocolate Chip Cookie
Tradition De France – Croissant 
Kerr Street Café – Flat White (and stay for Brunch)
Tatin Bakehouse - Canele Earl Grey Cake

5.    Listen to Live Music

TD Music Series in the Square | Downtown Oakville | Saturdays & Sundays in August | 2PM – 6PM

Downton Oakville venues presenting local talent. This August, experience the heart and soul of summer in Downtown Oakville with the TD Summer Music Series! Enjoy free outdoor performances every Saturday and Sunday from 2 PM to 6 PM across three walkable venues in Downtown Oakville. 

Friday Night Jazz | Oakville Towne Square, 94 George St | 7PM - 9PM 

Swing into the weekend with the smooth sounds of jazz! Every Friday evening through the summer local artists bring classic jazz vibes to life. Perfect for music lovers and date nights alike. Don’t miss the rhythm, the groove, and the magic of live music every Friday night this August.

6.    Best Oakville Patios for Outdoor Dining This Summer

Summer in Oakville screams patio time! There are so many great patios in the community but these are some of our current favourites. 

Plank Restobar – Poke Spoons Appetizer
Bronte Boathouse – Peach Burrata Salad
Ce Soir Brasserie + Bar – Mushroom Ravioli & Ce Soir Burger
Maro’s – Proud Mama’s Bella and the Beast
Stoney’s Bread Company – Nove Sandwich 
Hexagon Restaurant – Tasting menu always! 

Ce Soir Brasserie + Bar, Downtown Oakville

7.    Have Yourself a Sweet Treat

The Robertson Kadwell genes hold a strong sweet tooth, so trips for ice cream and gelato have to be included in this list. 

Farma Greek by Colossus Greek Taverna – Soft Serve Greek Yogurt
La Dolce Vita – Pistachio or Blood Orange Gelato
The Flavour Fox – Salted Caramel Gelato 
Chocolato & Tommy Café – Banana Split Sundae

8.    Family Fun 

Movies in the Park | Oakville Parks | Wednesdays & Thursdays in August | 6:30PM 

Bring a picnic blanket and your favourite snacks to enjoy a free movie, plus family-friendly activities at a park near you. Entry and family-friendly activities begin at 6:30 p.m. with the movie beginning around dusk (approximately 8:30 p.m.). Arrive early to ensure you get a good spot to watch the main feature, have a chance to connect with friends and neighbours, and take part in Oakville Public Library activities.

Community Swim | Oakville Community Pools | Weekdays | Afternoons & Evenings

Enjoy family-friendly evening leisure swims at our outdoor pools this summer! Community Centres open their doors for free swim and play evenings through the summer.

Summer Splash | Oakville Parks | Wednesdays | 6PM – 8PM

Oakville Fire crews will are visiting splash pads around Town as they connect with the community though the Summer Splash campaign. Families are invited to meet fire crews, check out fire trucks and learn about fire safety.

8.    Go for a Paddle in Sixteen Mile Creek

Enjoy some relaxing time on the water, whether it be stand up paddle boarding (SUP) in Sixteen Mile Creek or kayaking out to Lake Ontario. It is super easy to rent boats and gear through companies like Paddle Sport Performance. Thinking you want to do it more regularly? Check out some of the great programs run by Burloak Canoe Club, options for the kids and adults. 

Stand Up Paddle Boarding in Lake Ontario

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