Our Big Roundup of Community Events in Oakville, Ontario

ByOak Ville Rising Events
group of friends stacking hands

Are you among the 77% of Canadians who are feeling bored?

One of the greatest things you can do is reach out to your community to have fun together. Oakville is one of the most incredible places to live and visit since there’s always stuff on the calendar.

What are some of the top Oakville community events? Read on for our favourite events in Oakville.

Midnight Madness

Kick off your summer with Midnight Madness, one of Oakville’s most beloved events. Held each year in July, Midnight Madness transforms downtown Oakville into a bustling hub of excitement. Stroll along Lakeshore Road as shops stay open until midnight, offering special deals and promotions.

Live music fills the air, and delicious food vendors line the streets, creating a festive atmosphere that draws crowds from near and far. It’s the perfect opportunity to shop, dine, and experience the vibrant energy of Oakville at night.

Bronte Harbour Annual Tree Lighting

Embrace the holiday spirit at the Bronte Harbour Annual Tree Lighting ceremony. Held in December, this heartwarming event brings the community together to celebrate the festive season. Gather with friends and family at Bronte Heritage Park as the majestic tree is illuminated with thousands of twinkling lights.

Enjoy live performances, festive treats, and even a visit from Santa Claus himself. It’s a magical evening that captures the essence of community and joy. It’s one of the nicest things to do in Oakville during the holidays.

Oakville Children’s Festival

Let your imagination soar at the Oakville Children’s Festival, a day of fun and creativity for the whole family. Held in August at Queen Elizabeth Park Community and Cultural Centre, this event features a wide array of the following:

  • Interactive activities
  • Performances
  • Workshops designed to inspire and entertain children of all ages

From arts and crafts to storytelling and live entertainment, there’s something for everyone to enjoy. All families need to add this to their Oakville event calendars.

Oakville Family Ribfest

Calling all barbecue enthusiasts! Don’t miss the Oakville Family Ribfest, an annual celebration of mouthwatering ribs and live entertainment. Held in Sheridan College’s Trafalgar Campus, this event brings together top rib vendors from across North America to compete for the title of best ribs.

Sink your teeth into juicy ribs, savour delicious sides, and groove to live music performances throughout the weekend. With activities for all ages, including a kids’ zone and artisan market, it’s one of the tastiest Oakville events for the whole family.

Oakville Waterfront Festival

Dive into summer fun at the Oakville Waterfront Festival, a three-day extravaganza along the beautiful shores of Lake Ontario. Held in Coronation Park, this event showcases the best of Oakville’s waterfront with a variety of activities and attractions. You can do the following:

  • Explore artisanal vendors
  • Indulge in gourmet food trucks
  • Enjoy live music performances against the backdrop of the serene lake

Adults can sip on some beer while little ones can play in the dedicated kids’ zone. There’s something for everyone to enjoy at this waterfront celebration.

Oakville Farmers’ Market

Experience the vibrant flavours of Oakville at the Oakville Farmers’ Market, a weekly gathering of local vendors offering fresh produce, artisanal goods, and delicious treats. Held every Saturday from May to October in downtown Oakville, this market is a celebration of community and culinary delights.

Browse the stalls filled with seasonal fruits and vegetables, handcrafted goods, and gourmet delicacies sourced from local farmers and artisans. It’s the perfect place to shop local, support small businesses, and enjoy the bounty of the region.

Downtown Oakville Jazz Festival

Jazz enthusiasts rejoice at the Downtown Oakville Jazz Festival, a weekend-long celebration of smooth tunes and cool vibes. Held each year in August, this free outdoor event features performances by top jazz musicians from across Canada and beyond. Wander through downtown Oakville as various stages showcase the finest jazz, blues, and swing songs.

From intimate performances in local cafes to lively concerts in Towne Square, there’s no shortage of soulful music to enjoy. Bring a lawn chair, grab a bite to eat from nearby restaurants, and soak in the melodious atmosphere.

Oakville Film Festival

Lights, camera, action! Film buffs won’t want to miss the Oakville Film Festival, a showcase of independent cinema from around the world. Held in June at various venues throughout Oakville, this multi-day event celebrates the art of filmmaking with the following:

  • Screenings
  • Q&A sessions
  • Special events

Discover compelling narratives, thought-provoking documentaries, and groundbreaking films that push the boundaries of storytelling. Whether you’re a cinephile or looking for something different to do in Oakville, the Oakville Film Festival will enrich you like never before.

Oakville Half Marathon

Anyone who’s looking for fitness activities in Oakville should grab their running shoes and go to the Oakville Half Marathon. It’s an annual event that combines fitness and community spirit. Held in September, this popular race attracts newcomers and experienced runners alike.

The scenic course takes participants through picturesque neighbourhoods, along the waterfront, and past iconic landmarks. It gives each participant a memorable and invigorating racing experience. Whether you’re racing for a personal best or enjoying the camaraderie of fellow runners, the Oakville Half Marathon is a must-attend event for fitness enthusiasts and spectators.

There are cheering spectators, live music along the course, and post-race celebrations. It’s a thrilling event that promotes wellness and community spirit.

Oakville Downtown Ghost Walks

Embark on a journey into Oakville’s haunted history with the Oakville Downtown Ghost Walks, a spine-tingling experience that explores the town’s eerie past. Led by knowledgeable guides, these guided walking tours take participants on a ghostly adventure through the streets of downtown Oakville. It reveals chilling tales of the following:

  • Paranormal encounters
  • Mysterious happenings
  • Lingering spirits

Whether you’re a skeptic or a believer, the Oakville Downtown Ghost Walks offer a fascinating blend of history, folklore, and supernatural intrigue that is sure to send shivers down your spine.

Oakville Family Day Winterfest

Beat the winter blues and celebrate family fun at the Oakville Family Day Winterfest, an annual event held in February. This winter wonderland extravaganza offers a wide range of activities and attractions for all ages. It includes the following:

  • Outdoor skating
  • Tobogganing
  • Snowshoeing
  • More

Warm up by the fire pits with hot cocoa and marshmallows, or participate in arts and crafts workshops and interactive games. With live entertainment and food vendors serving up delicious treats, the Oakville Family Day Winterfest is the perfect way to embrace the magic of winter and create cherished memories with loved ones.

Oakville Makers’ Market

Discover unique treasures and support local artisans at the Oakville Makers’ Market, a monthly showcase of handmade goods and crafts. Held on select weekends throughout the year at various locations in Oakville, this curated market features a diverse array of products. It includes the following:

  • Jewelry
  • Pottery
  • Textiles
  • Woodworking
  • More

Meet the makers behind the creations, learn about their craft, and shop for one-of-a-kind gifts and keepsakes. The Oakville Makers’ Market offers a delightful shopping experience that celebrates creativity and craftsmanship.

Oakville Outdoor Movie Nights

Experience the magic of cinema under the stars at Oakville Outdoor Movie Nights, a series of free outdoor film screenings held during the summer months. Pack up some lawn chairs and cozy blankets and head to select parks and public spaces in Oakville for an evening of family-friendly entertainment.

From beloved classics to recent blockbusters, each screening offers a different movie-going experience for audiences of all ages. Pack a picnic dinner or purchase snacks from food vendors on-site, and enjoy a memorable night out under the open sky.

Oakville Retrofest

Step back in time and relive the nostalgia of decades past at Oakville Retrofest, an annual celebration of vintage cars, music, and culture. Held in downtown Oakville in August, this retro-inspired event features a dazzling display of classic cars and motorcycles from the 1950s, 60s, and 70s, lovingly restored to their former glory. You can do the following:

  • Stroll along the streets lined with vintage vehicles
  • Enjoy live performances of retro music and dance
  • Browse retro-themed vendors offering memorabilia and collectibles

Whether you’re a vintage enthusiast or appreciate the timeless charm of yesteryear, Oakville Retrofest offers a fun and nostalgic experience for all.

Oakville Winter Beer Festival

Warm up with good cheer and great beer at the Oakville Winter Beer Festival, an annual celebration of craft brews and winter festivities. Held in January, this outdoor beer festival brings together local breweries and cideries to showcase their finest seasonal offerings. Sample a wide selection of beers, ciders, and specialty beverages, each carefully crafted to warm you from the inside out.

Pair your drinks with delicious bites from food trucks and vendors, and enjoy live music performances in a festive atmosphere. The Oakville Winter Beer Festival is the place to be if you love event planning in winter.

Oakville Yoga Festival

Find inner peace and rejuvenation at the Oakville Yoga Festival, a day-long event dedicated to wellness and mindfulness. Held in June at various locations throughout Oakville, this festival offers a diverse lineup of the following:

  • Yoga classes
  • Workshops
  • Wellness activities for practitioners of all levels

From sunrise yoga sessions to meditation workshops and holistic healing therapies, there’s something for everyone to explore and experience. Connect with like-minded individuals, learn from knowledgeable instructors, and embrace the transformative power of yoga in a supportive and inclusive community environment.

Oakville Harbour Day

Dive into maritime history and waterfront fun at Oakville Harbour Day, an annual event celebrating the town’s nautical heritage. Held in June at the picturesque Oakville Harbour, this family-friendly event has a bunch of activities for all ages. You can do the following:

  • Explore historic ships
  • Take guided tours of the harbour
  • Learn about Oakville’s rich maritime history through interactive exhibits and demonstrations

With live music, delicious food vendors, and children’s activities, Oakville Harbour Day is a delightful way to spend a day by the water.

Oakville Family Fun Fair

Get ready for a day of thrills and excitement at the Oakville Family Fun Fair, a carnival-style event that promises fun for the whole family. Held annually in May at Bronte Creek Provincial Park, this fair features a wide array of rides, games, and attractions to delight visitors of all ages.

From classic carnival games to adrenaline-pumping rides, there’s something for everyone to enjoy. You can do the following:

  • Indulge in tasty treats from food vendors
  • Participate in contests and giveaways
  • Create fabulous memories with friends and family at this festive event

Oakville Winter Carnival

Embrace the magic of winter at the Oakville Winter Carnival, a festive celebration of all things snowy and fun. Held in January at various locations throughout Oakville, this event offers a wide range of winter activities for families and individuals alike.

From ice skating and snowshoeing to tobogganing and ice sculpting, there’s no shortage of cold-weather fun to be had. Warm up with hot cocoa and cozy treats, enjoy live entertainment, and marvel at the beauty of winter in Oakville at this enchanting carnival.

Oakville Music Festival

Immerse yourself in the melodious sounds of the Oakville Music Festival, an annual showcase of local talent and musical diversity. Held in April at various venues throughout the town, this event features performances by musicians representing a wide range of genres.

Whether you’re a music aficionado or love live entertainment, the Oakville Music Festival offers something for everyone to enjoy. Visitors can do the following:

  • Support local artists
  • Discover new bands
  • Experience the vibrant music scene in Oakville

Oakville Garden Tour

Explore the beauty of Oakville’s gardens at the Oakville Garden Tour, an annual event that showcases the town’s most exquisite private gardens. Held in June, this self-guided tour allows visitors to wander through stunning landscapes, floral displays, and tranquil retreats tucked away in Oakville’s neighbourhoods.

From lush backyard gardens to curated landscapes, each stop on the tour offers inspiration and insight into the art of gardening. Whether you’re a seasoned gardener or appreciate natural beauty, the Oakville Garden Tour is a must-see event for plant enthusiasts.

Oakville Craft Beer Festival

Raise a glass to local brews at the Oakville Craft Beer Festival, an annual celebration of Ontario’s craft beer industry. Held in August at the picturesque Coronation Park, this event brings together breweries from across the province to showcase their finest creations.

Sample a wide variety of craft beers, ciders, and spirits, and meet the masterminds behind the brews. With live music, food trucks, and games, the Oakville Craft Beer Festival is a laid-back and enjoyable way to discover new flavours and support local breweries.

Oakville Art in the Park

Experience the creativity and talent of Oakville’s artistic community at Art in the Park, an outdoor art exhibition held annually in August at Bronte Heritage Waterfront Park. Stroll along the picturesque waterfront as you admire photography, paintings, jewelry, and more. You can do the following:

  • Meet local artists
  • Purchase unique pieces for your home or collection
  • Enjoy live art demonstrations and performances

With stunning lake views as a backdrop, Art in the Park offers a scenic and inspiring setting to appreciate the arts in Oakville.

Oakville Food Truck Festival

Indulge your taste buds at the Oakville Food Truck Festival, a mouthwatering event that celebrates the diverse culinary offerings of the region. Held each year in July at Bronte Heritage Waterfront Park, this festival brings together some of the most incredible food trucks in the region.

From gourmet burgers and tacos to decadent desserts and savoury snacks, there’s no shortage of options to satisfy your cravings. Enjoy live music, family-friendly activities, and a bustling atmosphere as you feast on delectable fare at this popular foodie event.

Oakville Art Tour

Immerse yourself in Oakville’s thriving arts scene with the Oakville Art Tour, an annual showcase of the town’s finest galleries, studios, and creative spaces. Held in September, this self-guided tour invites art enthusiasts to explore a diverse range of ceramics, paintings, mixed media, and more.

Meet local artists, gain insight into their creative process, and discover hidden gems tucked away in Oakville’s vibrant arts community. Even if you’re not a collector, you’ll still love this event since it gives you a chance to connect with the town’s cultural heritage.

Oakville Haunted Walk

Brace yourself for a spine-tingling adventure on the Oakville Haunted Walk, a guided tour that explores the town’s eerie history and ghostly legends. Held in October, this immersive experience takes participants on a journey through Oakville’s haunted past, visiting historic sites and landmarks rumoured to be haunted by restless spirits.

Led by knowledgeable guides, the Oakville Haunted Walk offers a blend of history, folklore, and spine-chilling tales that will leave you both terrified and intrigued. Whether you’re a skeptic or a true believer in the supernatural, this ghostly tour promises an unforgettable evening of thrills and chills.

Oakville Winter Wonderland

Oakville Winter Wonderland is a festive celebration that infuses magic into this charming town. Held in December, this family-friendly event offers a host of seasonal activities and attractions for all ages to enjoy. Guests can do the following:

  • Go skating at the outdoor rink
  • Marvel at dazzling light displays
  • Warm up by the crackling bonfires with hot cocoa and marshmallows

With visits from Santa Claus, live entertainment, and holiday crafts, Oakville Winter Wonderland is a perfect experience. People of all ages can feel inspired by the glow of the holiday season.

Oakville Vintage Car Show

Step back in time and admire classic automobiles at the Oakville Vintage Car Show. It’s an annual gathering of vintage and antique cars from across the decades.

Held in June at Bronte Creek Provincial Park, this nostalgic event showcases beautifully restored vehicles that evoke memories of bygone eras. Visitors can do the following:

  • Stroll through rows of maintained cars
  • Chat with passionate owners
  • Marvel at the craftsmanship and design of these automotive treasures

There also happens to be food, music, and other awesome activities. The Oakville Vintage Car Show offers a delightful day out for car enthusiasts and history buffs alike.

Oakville Photography Festival

Capture the beauty of Oakville through the lens at the Oakville Photography Festival, a celebration of visual storytelling and artistic expression. Held in May at various locations throughout the town, this event showcases the work of local photographers through exhibitions, workshops, and interactive experiences.

Whether you’re a seasoned photographer or an amateur enthusiast, the Oakville Photography Festival offers opportunities to do the following:

  • Hone your skills
  • Connect with fellow photographers
  • Explore the town’s scenic landscapes and architectural landmarks from a new perspective

Oakville Summer Concert Series

Groove to the rhythm of live music at the Oakville Summer Concert Series. It’s a weekly outdoor concert series that showcases talented musicians and bands from across the Oakville region. Held throughout the summer months at various parks and outdoor venues, this free concert series offers a diverse lineup of musical genres.

Bring a lawn chair, pack a picnic, and bask in the gorgeous music under the stars with friends and family. Whether you’re a music lover or looking for a fun and relaxing way to spend a summer evening, the Oakville Summer Concert Series offers a memorable outdoor entertainment experience for all.

Oakville Dog Festival

Grab your dog’s leash to go frolic at the Oakville Dog Festival. This annual dog event celebrates the wonderful bond between humans and their furry friends. Held in September at Coronation Park, this canine-centric festival features all kinds of activities for dogs of all breeds and sizes.

From agility courses and obedience demonstrations to pet-friendly vendors and doggy fashion shows, there’s something for every four-legged friend to enjoy. People can do the following:

  • Meet other dog lovers
  • Learn about pet care and training
  • Bond with their pups in a welcoming community atmosphere

You’ve Got to Check Out These Community Events in Oakville, Ontario

As you can see, there are countless Oakland community events that bring everyone together. Be sure to add all of these Oakland events to your calendar this year.

Would you like to stay in the loop when it comes to upcoming events in Oakland, real estate trends, and other fun developments? Keep Oakville Rising’s blog in your bookmarks so you never miss out.