13 Things To Do In Windsor, Canada

Paul Williams -

Tucked along the shimmering Detroit River, Windsor, Canada, is a city that instantly captivates with its mix of history, charm, and vibrant culture. On my first visit, I wasn’t sure what to expect, but as I walked through the lush Dieppe Gardens, the peaceful atmosphere and stunning views of the Detroit skyline took me by surprise. There's something magical about standing on Windsor’s waterfront, feeling the breeze off the river, and watching the city come to life.

Windsor is a place where every street, park, and landmark tells a story. From the historic elegance of Olde Walkerville, with its craft breweries and century-old distilleries, to the modern energy of its art galleries and festivals, this city offers something for everyone. I found myself getting lost in the beauty of the Windsor Sculpture Park, where larger-than-life sculptures blend seamlessly with the natural landscape.

Beyond its sights, Windsor feels welcoming, like a city that’s proud of its heritage yet embraces the present. The mix of picturesque wineries, sprawling green spaces, and lively local culture made me feel connected to the heart of the city. Windsor isn’t just a stop on the map—it’s a destination that leaves a lasting impression.

1. Stroll Through Dieppe Gardens

Located along Windsor’s scenic riverfront, Dieppe Gardens is a must-visit destination for anyone seeking relaxation and beautiful views. This charming park offers visitors a peaceful place to unwind while enjoying stunning vistas of the Detroit skyline. Named after the brave soldiers who fought in the Dieppe Raid during WWII, Dieppe Gardens is more than just a picturesque location—it's also a significant historical site. Walk along the river, admire the vibrant flower beds, and pause to read the plaques commemorating Canadian military history.

Fun Fact: The Dieppe Raid, conducted on August 19, 1942, was a key learning experience for the Allies. The operation’s failure informed the planning of the successful D-Day landings in Normandy two years later.

2. Visit the Canadian Aviation Museum

For those looking for unique attractions in Windsor, the Canadian Aviation Museum offers an unforgettable experience. Home to an impressive collection of aircraft, the museum highlights Canada’s contributions to aviation. From vintage planes to modern marvels, each exhibit tells the story of Canada’s skies. Visitors can get up close to iconic planes and even take a ride in a historic warplane—an exciting opportunity for aviation enthusiasts! The museum also offers educational exhibits and interactive displays, making it one of the best family-friendly activities in Windsor.

This museum is not only a treasure for history lovers, but also a thrilling stop for anyone interested in technology and aviation. For those wondering what to do in Windsor, a visit here is a must.

Fun Fact: The Canadian Aviation Museum houses one of only two remaining airworthy Lancaster bombers, which played a critical role in WWII bombing missions.

If you're looking for a dose of culture and creativity, the Art Gallery of Windsor is the place to be. This cultural gem is home to an impressive collection of contemporary Canadian art, making it one of the most popular things to do in Windsor for art enthusiasts. The gallery features rotating exhibitions, ensuring that every visit offers something new and thought-provoking.

In addition to its exhibitions, the gallery hosts hands-on workshops and educational programs, making it a dynamic space for both locals and tourists.

Fun Fact: The Art Gallery of Windsor has a permanent collection of over 4,000 works of art, ranging from the early 19th century to contemporary pieces.

4. Wander through Jackson Park

For visitors seeking outdoor activities in Windsor, Jackson Park is a must-visit destination. Known for its expansive gardens, scenic fountains, and the iconic Queen Elizabeth II Sunken Garden, this park is one of Windsor’s largest and most picturesque green spaces.

The meticulously landscaped gardens are a favorite for photographers and nature lovers alike. Seasonal floral displays add vibrant color throughout the year, making it a popular spot for both locals and tourists. If you're searching for things to do in Windsor with family, this park provides ample space for children to run and play while adults can unwind on one of the many benches.

Fun Fact: Jackson Park is home to several war memorials, including the Essex Scottish Memorial, honoring local soldiers who fought in WWII.

5. Take a Tour of Willistead Manor

History buffs and architecture lovers will be captivated by Willistead Manor, a grand mansion built in 1906. Designed in the Tudor-Jacobean style, this architectural marvel is nestled in the heart of Windsor and surrounded by 15 acres of beautifully maintained gardens. For those interested in historical tours in Windsor, guided tours of the manor provide fascinating insights into the life of Edward Chandler Walker, the son of Hiram Walker, the famous whisky magnate.

The interior of Willistead Manor is just as impressive as its exterior, with its opulent woodwork, grand staircases, and period furnishings. It’s not just a stop for history enthusiasts; anyone can appreciate the craftsmanship and beauty of this iconic Windsor landmark.

Fun Fact: Despite its grandeur, Willistead Manor was never actually lived in by Edward Walker, as he passed away shortly after its construction.

6. Sip and Savor at a Local Winery

No visit to Windsor-Essex County would be complete without sampling the region’s renowned wines. Known for its award-winning wineries, the area boasts some of Ontario’s best wine experiences. Two standout wineries are Pelee Island Winery and Sprucewood Shores Estate Winery, both offering tastings that allow you to savor the region’s unique flavors. Thanks to the area’s distinctive microclimate, Windsor-Essex produces wines with rich, complex profiles, particularly their ice wines and Rieslings.

Sip a glass on a patio overlooking the vineyards, or take a tour to learn more about the winemaking process.

Fun Fact: Pelee Island Winery is the largest estate winery in Canada and sits on a unique island vineyard, which benefits from Lake Erie’s moderating effect on temperature, creating ideal conditions for growing grapes.

7. Enjoy the Waterfront Trail

For those looking to explore Windsor on foot or by bike, the Windsor Waterfront Trail is a must-see. This scenic pathway stretches along the Detroit River, offering stunning views of the water and the Detroit skyline. It’s one of the best free activities in Windsor, perfect for a leisurely walk, biking, or even rollerblading. Along the trail, you'll encounter parks, gardens, and sculptures, including the iconic "Great Canadian Flag" plaza, making this trail not only a recreational spot but also a cultural experience.

The trail connects many of Windsor’s top attractions, including Dieppe Gardens, Odette Sculpture Park, and Assumption Park, allowing visitors to easily explore the city’s beautiful riverfront.

Fun Fact: The Windsor Waterfront Trail is part of the larger Great Lakes Waterfront Trail system, which spans over 3,600 kilometers along the shores of Ontario’s Great Lakes, connecting communities and providing access to scenic natural landscapes.

8. Discover History at Fort Malden

Just a short drive from Windsor, Fort Malden National Historic Site offers an immersive experience in Canada’s military history. This well-preserved fort played a pivotal role in the War of 1812, serving as a key defense point for British forces. Today, Fort Malden operates as a living history museum, where visitors can explore the original buildings, watch historical reenactments, and engage with costumed interpreters who bring the past to life.

History lovers will appreciate the detailed exhibits that highlight the fort’s role during the conflict and its subsequent use in the Rebellion of 1837. Fort Malden is not only a place to learn about military strategy but also about the lives of soldiers and civilians who lived through these significant events.

Fun Fact: Fort Malden is home to the only intact barracks from the War of 1812 that still stands in Canada, offering a rare glimpse into the everyday life of soldiers from that era.

9. Gamble at Caesars Windsor Casino

For those in search of excitement, Caesars Windsor offers the perfect mix of entertainment and luxury. As one of Canada’s premier casinos, Caesars Windsor features an array of gaming options, from slots to poker tables. But the fun doesn’t stop there—this world-class casino is also home to several fine dining restaurants, luxury accommodations, and top-tier live entertainment, attracting big-name performers from around the world.

Even if you’re not a gambler, the lively atmosphere at Caesars Windsor makes it a great spot to visit for a night out. The casino’s prime location along the waterfront also offers spectacular views of the Detroit River, adding a touch of glamour to your visit.

Fun Fact: Caesars Windsor is the largest casino in Canada and was the first casino to open in Ontario, setting the standard for entertainment venues in the region.

10. Experience Windsor Sculpture Park

Art lovers and outdoor enthusiasts alike will appreciate Windsor Sculpture Park, a unique open-air museum that boasts over 30 large-scale sculptures created by internationally renowned artists. This riverside park is not only a haven for contemporary art but also offers stunning views of the Detroit River and skyline, making it a perfect stop for visitors looking for free things to do in Windsor. The expansive park provides a peaceful atmosphere where you can stroll, take in the scenery, and marvel at the impressive works of art.

Families will enjoy the space for its open paths and art pieces that encourage curiosity, while photography enthusiasts will find plenty of picturesque moments to capture.

Fun Fact: One of the most iconic sculptures in the park is the "The Eve’s Apple" by Edwina Sandys, the granddaughter of Winston Churchill, which reflects on themes of temptation and human nature.

11. Visit Olde Walkerville

Step into Olde Walkerville, one of Windsor’s most historic and charming neighborhoods, and you’ll feel like you’ve stepped back in time. Originally developed by Hiram Walker, the founder of Canadian Club Whisky, Olde Walkerville offers a unique glimpse into Windsor’s industrial past. Today, it’s a trendy area filled with boutique shops, cafes, and pubs, making it one of the best spots for both history buffs and those looking for a vibrant local scene.

Explore the area’s beautifully preserved architecture, which reflects the early 20th-century charm, or stop by the historic Hiram Walker & Sons Distillery for a tour.

Fun Fact: The streets of Olde Walkerville were designed to mimic the layout of a European village, complete with wide, tree-lined boulevards and grand, stately homes built for the executives of the distillery.

12. Tour the John R. Park Homestead

For an authentic glimpse into 19th-century life in rural Ontario, a visit to the John R. Park Homestead Conservation Area is a must. This well-preserved homestead, restored to its 1850s appearance, provides visitors with an immersive experience of what daily life was like for early settlers in the region. With period-accurate furnishings, heritage gardens, and hands-on demonstrations such as blacksmithing and traditional cooking, the homestead offers an educational and engaging experience for visitors of all ages.

If you’re a history lover or looking for a family-friendly activity in Windsor, the John R. Park Homestead provides a fascinating insight into the past while allowing you to interact with historical re-enactors.

Fun Fact: The John R. Park Homestead was originally built by John and Amelia Park, who emigrated from New York State in the 1830s, and is one of the few remaining pioneer homesteads in Ontario that is still open to the public.

13. Attend a Festival

Windsor is a city that knows how to celebrate, with an array of annual festivals that highlight its diverse culture, art, and music scenes. One of the city's most notable events is the Windsor International Film Festival (WIFF), which attracts filmmakers and film enthusiasts from across the country. If you’re into music, Bluesfest Windsor is one of the largest blues festivals in Canada, drawing crowds with its world-class performances.

These festivals provide the perfect opportunity to experience Windsor’s vibrant culture and meet locals while enjoying top-notch entertainment. With events happening year-round, there’s always something to see or do in Windsor.

Fun Fact: The Windsor International Film Festival (WIFF) is the largest volunteer-run film festival in Canada and has been showcasing independent films since 2005, making it a beloved event for filmmakers and cinephiles alike.

Conclusion

Windsor, Canada, is more than just a city—it’s an experience that wraps you in its charm and leaves you wanting more. As you stroll along the riverfront, with the Detroit skyline shimmering across the water, you’ll feel the heartbeat of this place.

There’s an energy here, a mix of old and new, where every corner tells a story—from the grandeur of Willistead Manor to the artistic vibe of Windsor’s Sculpture Park. It’s a city that invites you to slow down, breathe in the fresh river breeze, and take in the beauty around you. Windsor may not shout from the rooftops, but it has a quiet way of capturing your heart, making it a place you’ll be talking about long after you’ve left.

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FAQs

1. How far is Windsor, Canada, from Detroit?

Windsor is directly across the Detroit River from Detroit, Michigan. It’s just a short 5-minute drive via the Detroit-Windsor Tunnel or the Ambassador Bridge, making it incredibly convenient for travelers visiting both cities.

2. What is Windsor, Canada, known for?

Windsor is best known for its rich automotive history, being home to Chrysler Canada and close to Detroit's automotive hub. Additionally, it's famous for Canadian Club Whisky, produced in the historic Hiram Walker & Sons Distillery in Olde Walkerville.

3. Is Windsor, Canada, worth visiting?

Absolutely! With its scenic riverfront views, historic neighborhoods like Olde Walkerville, cultural sites like the Art Gallery of Windsor, and nearby attractions like Fort Malden, Windsor offers a variety of experiences for all types of travelers.

4. What is the best time to visit Windsor?

The best time to visit Windsor is during the spring and summer months (May to September) when the weather is warm, and outdoor attractions like the Windsor Waterfront Trail and Jackson Park are at their most beautiful. Fall is also a lovely time, especially during harvest season at the local wineries.

5. How many days do you need to explore Windsor?

You can enjoy the highlights of Windsor in two to three days, but if you want to explore nearby attractions like Pelee Island or dive deeper into the city’s cultural and historical sites, an extended stay of four to five days is ideal.

6. Can you visit wineries near Windsor?

Yes! Windsor-Essex County is home to several award-winning wineries, including Pelee Island Winery and Sprucewood Shores Estate Winery, where visitors can enjoy wine tastings, vineyard tours, and scenic views.

7. What are some free things to do in Windsor?

Windsor offers several free activities, including a walk along the Windsor Waterfront Trail, exploring Dieppe Gardens, visiting Windsor Sculpture Park, and strolling through Jackson Park, making it a budget-friendly destination for travelers.