Sing and Dance Your Way Through Oakville This Spring

Spring is upon us! With the days getting longer (and hopefully sunnier) and the coldest months behind us, there is a new energy in the air that makes us excited to get outside and try new things. Follow this two-day itinerary as we break down must-see and do locations around Town that will help ignite your adventurous spirit through Oakville’s art, music, and entertainment scene.

Day One

Exploring Downtown Oakville and Kerr Village

Check into your hotel, then hit the streets of Downtown Oakville, home to many boutique stores, art galleries, bakeries, and restaurants. Walk the streets and window shop at the many unique stores throughout the area. Key businesses to keep an eye out for are:

• The Native Art Gallery in Towne Square. This Gallery is dedicated to showcasing Canada’s Indigenous artists.
• Oakville Art Galleries in Centennial Square.
• The Witch’s Fix a store for those looking to connect with their mystical side.
• Must Boutique, Visit Oakville’s Talk of the Town winner for best apparel.
• Sugar Suite, Visit Oakville’s Talk of the Town winner for best bakery and Black Forest Bakery, Visit Oakville’s Talk of the Town winner for best pies.
• Or try your luck at Claw City, an indoor arcade and snack shop.

For lunch, stop at Figaro Coffee House. This café often hosts live music, open mic comedy shows, and sip and paint events. Visit their Instagram page here to see if there are any upcoming events that align with your stay in Oakville.  

After you have had your lunch at Figaro Coffee House, head to Kerr Village for some virtual reality fun. Another World VR Arena is opening in Oakville on March 14. This VR arena is home to many different rooms and themes, including Ghost Tower: Dance, which will be sure to get your adrenaline pumping and feet moving.

After you have danced your way to victory, head to Tannery Park for some sunshine and lakeside views. Grab a coffee, tea, or hot chocolate at Wet Coffee on your way to the park.  

For dinner, visit the Gingerman Social Corner. Not only does this restaurant serve delicious pub-style food, but it also hosts live music on Friday and Saturday evenings. Visit here to view their upcoming performances.

If you are visiting during the week, The Oakville Pump and Patio has bingo with a twist every other Monday and trivia and wine Wednesdays along with live music on Saturdays.

End your evening with a show at the Moonshine Café or at the Oakville Centre for the Performing Arts. The Moonshine Café has entertainment almost every night of the week, including live music, open mic nights, and improv shows.

Notable upcoming performances at the Oakville Centre for the Performing Arts include two-time JUNO Award winner Tenille Townes, Just for Laughs Roads Show, Classic Albums Live: Slippery When Wet, and JUNO Award winner Jesse Cook.

Day Two

A Day of Art, Craft, and Live Music

Start your morning at Winston Churchill, Oakville’s Entertainment Centrum where you will find fun entertainment attractions such as Putt in Glow and Dave and Busters. Spend your morning challenging your friends to fun arcade games at Dave and Busters and glow-in-the-dark mini putt at Putt in Glow. For those looking to take their trip to new heights, try indoor skydiving at iFly Oakville.

Next, make your way to Bronte Village for lunch. Along the way, stop at Gairloch Gardens. This beautiful garden has a scenic view of Lake Ontario, a rose garden, and is home to the Oakville Galleries. Enjoy the gardens at your leisure or inquire at the Galleries’ front desk about their A Large Slow River, 2000 audio walk by Canadian artist Janet Cardiff. You can borrow headphones at the Gallery and listen to the artist as they discuss the grounds.

After you have enjoyed the garden and gallery, stop at Por Vida in Bronte Village for lunch. This vibrantly decorated restaurant and winner of Visit Oakville’s best tacos will be sure to please your eyes as well as your stomach. This Mexican-style restaurant relaunched a new menu late last year, which offers Mexican staples like their surf and turf burrito, divorced enchiladas, birria quesadillas, and a wide variety of tacos to choose from.

Once you have enjoyed your lunch, make your way across the street to Artventures Studios. This studio is the perfect venue to release your creativity. They offer canvas, tote bag, and pottery painting workshops as well as pottery wheel throwing, watercolour workshops, and glass fusing. Visit here to view all their workshops. Reservations are highly recommended and will be prioritized over walk-ins. This Studio has locations across Ontario. When booking your reservation, make sure you are booking classes at their Oakville location.

After you are done at Artventures Studios, continue to explore the rest of Bronte Village. Head to Bronte Road and stop inside Lakeside Livin’, a nautical-themed store that sells artwork and home decor and My Girlfriend’s Closet, a clothing consignment store that is home to many hidden treasures. Continue your way down Bronte Road until you get to Bronte Heritage Waterfront Park. This park is home to over 100 Muskoka chairs that were hand-painted by residents, artists, business owners, and community groups across Oakville. Each chair is unique and tells its own story.

After you have explored Bronte Village, head to Easy on Fourth. This restaurant is a great venue for those looking to enjoy live entertainment with their meal. Easy on Fourth hosts a variety of trivia nights, karaoke, and live music. Visit their event page here to view their event schedule. 

Not ready to call it a night? Drive back to Winston Churchill and visit the Dirty Martini. On Fridays and Saturdays, a DJ transforms this venue into a dynamic nightclub where you can dance the night away.

This concludes this two-day itinerary, but your fun doesn’t need to stop here. Oakville has a wide range of art, music, and entertainment options throughout the year. Visit us again in the summer as our parks and streets come alive with the sound of music. Notable art-related events to look out for include:

• Oakville Festival of Film and Arts – Oakville’s ten-day film festival from June 17-27.
• Bachata Nights – learn to dance with the help of Tiana Adamas at the Bronte Market Square every Friday from June 19 – September 11.
• Bronte Lake Notes – a free weekly outdoor concert at Bronte Heritage Waterfront Park on Thursdays. The opening night will be announced soon.
• Oakville Wind Orchestra Sounds of Summer – enjoy free outdoor concerts at the Bronte Heritage Waterfront Park in the Butterfly Gazebo. Details coming soon.
• West End Jazz presents A Night to Remember on June 14. Listen to jazz music while you dine at the Oakville Conference Centre.
• Canada Day at the Bronte Legion – Live music, food trucks, and a vendor market at the Bronte Legion on July 1.
• The Summer Festival – in Downtown Oakville on July 18. Details coming coon!
• The Oakville Latino Festival – celebrate the Latin culture in Bronte Heritage Waterfront Park from July 24-26.
• Art in the Park– This event will feature more than 180 artists and artisans from across Canada on August 3 in Bronte Heritage Waterfront Park.   
• CRAFT Live Afro-Caribbean Canadian Waterfront Fete – celebrate the vast contributions and influencers of African, Caribbean, and black Canadians on August 29 at Bronte Heritage Waterfront Park.
• Kerrfest and Kerrfest Kids – enjoy live music, food vendors, a market and more at Westwood Park on September 11-13.

Visit here for a full list of Oakville events happening this year.