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Kick Up Your Heels, Summer is Almost Here: A Guide to Events and Pop-Ups Downtown.

Updated: 4 days ago

Summer in Downtown Oakville is shaping up to be an unforgettable season filled with events and pop-ups for just about everyone. Whether you’re a fitness enthusiast, food lover, or just looking to enjoy some time soaking up the sun outdoors, our lineup of summer events has something special just for you.

Summer Sweat Outdoor Fitness Series

Kickstart your mornings every Saturday in June and July, with a burst of energy at the Summer Sweat Outdoor Fitness Series. Hosted in Towne Square by our very own local fitness studios and experts, these classes offer a blend of exercises to rejuvenate both your body and mind. Classes are open for pre-registration starting May 15, so be sure to secure your spot! Presented in partnership with Hot Yoga & Pilates, FlySpin, and SPINCO

National Donut Day Celebration

Donut lovers, rejoice! Join us on June 7th in Towne Square for National Donut Day and indulge in a delicious free mini donut courtesy of Maverick's Donuts. We're giving away these tasty treats to the first 500 attendees starting at 3 PM. This is your chance to see why Downtown Oakville is the ultimate Donut Destination!

Shop the Street

Prepare for summer with the Shop the Street sidewalk sale event from June 13 to June 16. Downtown Oakville merchants will offer incredible deals both along the sidewalk and inside their stores. It’s a fantastic opportunity to snag some great finds and enjoy the beautiful weather.

FRESH Market

Starting June 9th and continuing every second Sunday through September, stroll through the FRESH Market on George Street. From 10:00 a.m. to 5:00 p.m., explore an assortment of handcrafted goods, plants, produce and treats. This market is the perfect spot to find unique items and support local.

Silent Disco: Summer Solstice Edition

Dance into the longest day of the year at our Summer Solstice Edition Silent Disco on June 22. From 5:00 p.m. to 9:00 p.m. in Towne Square, join us for an evening of music and fun. Sponsored by Celebrity Cruises and Expedia Cruises Oakville South, this event promises to be a night to remember.

Pop Up Ice Cream Shop - Free Gelato

 We’re celebrating International Ice Cream Day on July 21 by handing out free gelato to the first 500 people at our Pop-Up Ice Cream Shop in Towne Square. Thanks to our partnership with Il Gelato Di Carlotta, you can enjoy a cool treat on a hot summer day. The fun starts at 12PM.

Silent Meditation

Find peace and mindfulness at our Silent Meditation event on June 23 at 1 PM in Towne Square. Hosted in partnership with Saje, this 45-minute session using noise-canceling headphones will help you reconnect and relax. All participants will also receive a special gift from Saje.

Retro Roller Jam

Lace up for the Retro Roller Jam our pop up roller party happening along Navy Street on August 4th from 1 PM to 6 PM. Grab your tickets for this throwback event, complete with live DJ.

Candlelit Concerts with the Oakville Symphony Orchestra

Enjoy an enchanting evening with the first of two special Candlelit Concerts at Lakeside Park on August 10. The second concert, with members of the orchestra, will take place in Towne Square on August 24. Both events are in collaboration with the Oakville Symphony Orchestra and promise to be a magical atmosphere under the stars.

Boots in the Square

Get a little bit country right in the heart of Downtown Oakville on August 17th. Join us in Towne Square for live country music and pick up some new steps with line dance instruction courtesy of Fred Astaire Dance Studio.

TD Summer Music Series

Enjoy the sounds of summer at the TD Summer Music Series every Saturday and Sunday in July and August. Featuring live performances by local musicians, this free event in Towne Square is a great way to relax and soak up the summer vibe.

For more details on these events and to stay updated on additional pop-up events and activations, visit our website at  or follow us on Facebook and Instagram. This summer, Downtown Oakville is the place to be. See you there!

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