10 Diverse Year-Round Things to Do in Oshawa Canada

Key Takeaways:

• Oshawa offers a unique mix of nature, automotive history, arts, and lakefront charm that’s ideal for all seasons.

• Whether you’re exploring museums, hiking trails, or catching a festival, there’s always something happening in this underrated Ontario city.

• It’s a perfect getaway for families, culture lovers, and outdoor adventurers just an hour outside of Toronto.

Located on the shores of Lake Ontario, Oshawa is a thriving city in the Durham Region of Ontario with deep roots in both automotive history and natural beauty. Once primarily known as the home of General Motors Canada, Oshawa has grown into a vibrant destination for culture, education, and recreation. People love it for its balance—offering peaceful nature escapes, buzzing local events, and a rich museum scene all in one place. With easy access from Toronto and a more relaxed pace, Oshawa is becoming a go-to spot for year-round exploration. Whether you’re visiting for a day or a full weekend, it offers more than you expect—and delivers every time.

Table of Contents

1. Visit the Canadian Automotive Museum

2. Explore the Trails at Darlington Provincial Park

3. Catch a Show at the Regent Theatre

4. Walk the Waterfront at Lakeview Park

5. Wander Art Galleries at The Robert McLaughlin Gallery

6. Tour the Historic Parkwood Estate

7. Experience the Annual Peony Festival

8. Skate or Stroll at Memorial Park in Winter

9. Attend Live Music Nights in Downtown Oshawa

10. Shop Local at the Oshawa Centre and Downtown Markets

1. Visit the Canadian Automotive Museum

Oshawa’s automotive legacy takes center stage at the Canadian Automotive Museum, which houses an impressive collection of vintage and rare vehicles from around the world. Located in a beautifully preserved 1920s dealership building, this museum not only showcases classic cars but also tells the story of Canada’s deep relationship with auto manufacturing.

You’ll find exhibits on everything from early electric vehicles to race cars, and the knowledgeable staff add even more insight. It’s a hit with both gearheads and casual visitors, and there are often seasonal events or themed exhibits. If you’re into transportation history or want to show the kids a car older than their grandparents, this place is a gem.

2. Explore the Trails at Darlington Provincial Park

For outdoor lovers, Darlington Provincial Park is just minutes from downtown Oshawa and offers a refreshing escape into nature. With scenic hiking trails, beachfront views, and excellent birdwatching, it’s the perfect spot to walk, run, or picnic no matter the season. The park also has a campground and designated fishing areas, making it ideal for longer visits.

In summer, locals flock here for swimming and barbecues, while fall brings fiery foliage to the wooded trails. In winter, the landscape transforms into a snowy playground great for cross-country skiing or peaceful walks. It’s nature’s playground, and it’s right in Oshawa’s backyard.

3. Catch a Show at the Regent Theatre

Downtown Oshawa’s Regent Theatre is a restored 20th-century venue with old-school charm and a calendar packed with performances. From indie films and tribute concerts to community theater and university productions, the Regent offers something for everyone. Its intimate setting and rich history make every show feel special.

The theater is operated by Ontario Tech University and frequently hosts academic panels and public lectures, too. Whether you’re into classical music or stand-up comedy, checking the event calendar is a must. Grab a coffee or dessert nearby and enjoy an evening that feels both small-town cozy and culturally enriching.

4. Walk the Waterfront at Lakeview Park

Lakeview Park is one of Oshawa’s most beloved gathering spots, offering sweeping lake views, long walking paths, and grassy picnic areas. The paved trail along Lake Ontario is ideal for biking, strolling, or rollerblading with the sound of the waves nearby. In summer, the sandy beach is perfect for sunbathing or a quick dip.

You’ll also find playgrounds, sports fields, and even historical buildings like the Oshawa Museum, which gives a glimpse into 19th-century life in the region. Sunsets here are breathtaking, and weekend festivals often light up the park with food trucks and music. It’s a go-to spot for both relaxing and socializing.

5. Wander Art Galleries at The Robert McLaughlin Gallery

Art lovers shouldn’t miss The Robert McLaughlin Gallery, one of Ontario’s largest public art galleries outside of Toronto. Named after the founder of McLaughlin Motors (which later became part of GM), the gallery features contemporary Canadian art, photography, and Indigenous exhibitions that rotate throughout the year.

The sleek, modern space also offers workshops, kids’ art programs, and lectures that make art feel accessible and alive. Entry is often free or by donation, and the gallery’s gift shop has unique locally made items. Whether you’re a serious collector or a casual browser, the RMG is a cultural anchor in Oshawa.

6. Tour the Historic Parkwood Estate

One of Oshawa’s crown jewels is the Parkwood Estate, once home to Canadian auto baron R.S. McLaughlin. This grand mansion is a National Historic Site of Canada and offers guided tours of its opulent rooms, formal gardens, and architectural details that reflect early 20th-century luxury. Fans of classic films might recognize Parkwood—it’s been featured in movies like X-Men and Billy Madison.

Visitors can explore the stately halls, greenhouse, and even the lavish Art Deco indoor pool. Seasonal events, tea services, and holiday-themed tours make it worth visiting more than once a year. Whether you’re into architecture, history, or just want a glimpse of the city’s high society past, Parkwood delivers elegance and intrigue.

7. Experience the Annual Peony Festival

Every June, Oshawa blooms with color during the Peony Festival, held at the Oshawa Valley Botanical Gardens. This award-winning event showcases over 300 varieties of peonies in full bloom, alongside live music, artisan vendors, and garden tours. Nature lovers and photographers flock here to take in the vibrant displays.

The festival is free to attend and family-friendly, with kids’ activities, food trucks, and cultural performances adding to the festive vibe. Even if you’re not a gardener, it’s hard not to be wowed by the rows of fragrant blossoms and community spirit. It’s one of Oshawa’s signature events and an Instagrammer’s paradise.

8. Skate or Stroll at Memorial Park in Winter

In winter, Memorial Park transforms into a seasonal hub of lights, cheer, and cozy outdoor activities. A pop-up skating rink often appears during the holiday season, surrounded by festive lights and local vendors serving hot cocoa and treats. It’s a charming place to celebrate winter without the big-city crowds.

Located right downtown, it’s also the site for tree lightings, carolers, and outdoor markets. If skating isn’t your thing, bundle up and enjoy the snow-covered paths and nearby cafés. The city keeps the space lively and inviting through the colder months, making it a great stop for winter travelers.

9. Attend Live Music Nights in Downtown Oshawa

Downtown Oshawa has a growing live music scene, with bars, breweries, and lounges hosting regular shows that range from indie rock to jazz and country. Spots like The Atria and Biltmore Theatre offer intimate performances with local and touring artists in cozy, welcoming atmospheres.

Throughout the year, you can also catch outdoor concerts, open mic nights, and DJ events in public squares or seasonal festivals. The scene is inclusive, affordable, and full of energy, making it a great way to mingle with locals and unwind after a day of sightseeing.

10. Shop Local at the Oshawa Centre and Downtown Markets

For a mix of big-name brands and local finds, the Oshawa Centre is the region’s largest mall, featuring over 200 stores, restaurants, and services. It’s perfect for a rainy day or some retail therapy, with everything from fashion to home décor.

If you prefer local flair, downtown Oshawa’s farmers’ markets and craft fairs offer handmade goods, fresh produce, and unique gifts. Markets run through spring, summer, and fall, often in tandem with city events and live entertainment. Whether you’re buying or browsing, shopping in Oshawa feels more personal than in many larger cities.

What to Do if You Have Kids?

Oshawa is full of family-friendly fun for kids of all ages. Head to Lakeview Park for beach days and playgrounds, or explore interactive exhibits at the Canadian Automotive Museum. The Robert McLaughlin Gallery and Oshawa Public Library both offer year-round kids’ workshops and storytime events. During the summer, splash pads and outdoor concerts pop up around town, while in winter, ice skating and seasonal light shows keep the little ones entertained. With accessible transit and welcoming spaces, it’s a stress-free destination for traveling families.

Where Can I Find Free Events in Oshawa Canada Taking Place This Weekend?

To uncover free events in Oshawa this weekend—whether it’s a music night, street fair, museum opening, or outdoor yoga class—head over to PlanMyWeekend.ai. Just type “Oshawa” and filter by date and interest to find hidden gems happening nearby. The platform curates both popular and low-key happenings, making it easy to enjoy the city without spending a dime. Whether you’re into art, fitness, food, or family fun, this tool is your local go-to.

Final Thoughts on Planning a Trip Here

Oshawa is proof that you don’t need to travel far from Toronto to discover something special. It’s a city of balance—between nature and industry, heritage and modern flair, relaxation and entertainment. Whether you’re visiting for a weekend escape, a cultural deep dive, or an active family outing, Oshawa makes it easy to fill your days with memorable experiences. Come for the cars or the peonies, stay for the lakeside walks, music nights, and local flavor—this Ontario gem will surprise you, in every season.