13 Things To Do In Windsor, Canada
Tucked along the shimmering Detroit River, Windsor, Canada, offers a captivating blend of rich history, vibrant culture, and natural beauty. Known as the "City of Roses", Windsor enchants visitors with its stunning waterfront views, historical landmarks, and lively arts and dining scenes. On my first visit, I was struck by the peaceful atmosphere of Dieppe Gardens and the juxtaposition of lush green spaces with the bustling energy of the nearby Detroit skyline.
Windsor is more than its picturesque parks and charming streets—it’s a city where history and modernity coexist seamlessly. From the iconic Windsor Sculpture Park, featuring larger-than-life artworks, to the craft breweries and distilleries in historic Olde Walkerville, Windsor offers something special for every kind of traveler.
In this guide, discover the best things to do in Windsor—from peaceful riverfront strolls to unique cultural and historical attractions, each offering a glimpse into the heart of this vibrant city.
1. Stroll Through Dieppe Gardens
Dieppe Gardens is a jewel along Windsor’s waterfront, offering breathtaking views of the Detroit River and skyline. This peaceful park, named in honor of Canadian soldiers who fought in the Dieppe Raid during WWII, blends beauty with history. Visitors can enjoy vibrant flower beds, serene walking paths, and informative plaques that commemorate Windsor’s connection to Canadian military heritage.
This tranquil spot is perfect for reflection, relaxation, or capturing stunning photos.
Fun Fact: The Dieppe Raid of 1942, though a military failure, provided critical insights that influenced the planning of the successful D-Day landings in Normandy during WWII.
2. Visit the Canadian Aviation Museum
A visit to the Canadian Aviation Museum is an exciting and educational experience for all ages. The museum houses an impressive collection of aircraft that showcase Canada’s rich aviation history, from vintage planes to modern aircraft. Visitors can get up close to iconic planes, such as a rare airworthy Lancaster bomber, and even enjoy the thrill of a ride in a historic warplane.
Interactive displays and hands-on exhibits make the museum a hit with families, while aviation enthusiasts will be drawn to the intricate details and stories behind each aircraft. The museum’s focus on Canada’s contributions to aviation and its role in WWII adds depth to this unique attraction.
Fun Fact: The museum’s Lancaster bomber is one of only two in the world still capable of flying, a testament to the dedication of the museum’s restoration team.
3. Explore the Art Gallery of Windsor
Art enthusiasts will love the Art Gallery of Windsor, a cultural hub showcasing a diverse collection of contemporary Canadian art. With over 4,000 pieces in its permanent collection, the gallery captures a wide range of artistic styles, from early 19th-century works to cutting-edge contemporary pieces. Rotating exhibitions ensure that every visit brings fresh inspiration, and the gallery's workshops and educational programs make it a dynamic space for creativity and learning.
Fun Fact: The Art Gallery of Windsor is home to one of Canada’s most extensive collections of regional contemporary art, spotlighting the unique artistic voices of Ontario and beyond.
4. Wander through Jackson Park
For those craving a scenic outdoor escape, Jackson Park is a Windsor highlight. Spanning over 60 acres, the park features meticulously maintained gardens, iconic fountains, and the striking Queen Elizabeth II Sunken Garden. With vibrant floral displays changing seasonally, it’s a haven for photographers and nature enthusiasts.
Jackson Park is also steeped in history, hosting several war memorials, including the Essex Scottish Memorial, which honors local WWII soldiers. Its wide open spaces and charming paths make it perfect for leisurely walks, family outings, or a moment of peace in nature.
Fun Fact: Jackson Park is often referred to as the “Jewel of Windsor” due to its lush gardens and prominent role in the city’s cultural and historical fabric.
5. Take a Tour of Willistead Manor
Step back in time with a visit to Willistead Manor, a Tudor-Jacobean mansion built in 1906 by Edward Chandler Walker, son of Hiram Walker, the famed whisky magnate. Though Edward never lived in the home, the manor remains a testament to his family’s legacy. Situated on 15 acres of gardens, the manor’s grand architecture, intricate woodwork, and period furnishings transport visitors to an era of opulence and craftsmanship.
Guided tours offer rich insights into Windsor’s history and the Walker family’s influence on the region. The surrounding Willistead Park provides a tranquil space to enjoy after your visit.
Fun Fact: Willistead Manor was designed by famed Detroit architect Albert Kahn, who also designed Michigan Central Station and the Fisher Building.
6. Sip and Savor at a Local Winery
Windsor-Essex County is a hidden gem in Ontario’s wine country, boasting award-winning wineries that highlight the region’s unique terroir. Two must-visit spots are Pelee Island Winery, known for its sustainable practices and ice wines, and Sprucewood Shores Estate Winery, the only beachfront winery in Ontario.
Take a vineyard tour, savor a wine flight on a patio overlooking the lush rows of grapevines, and learn about the art of winemaking from passionate vintners.
Fun Fact: Pelee Island Winery is Canada’s largest estate winery, benefiting from Lake Erie’s moderating climate to produce exceptional wines with distinct flavor profiles.
7. Enjoy the Waterfront Trail
For outdoor enthusiasts, the Windsor Waterfront Trail is a must. This scenic pathway runs along the Detroit River, offering breathtaking views of the skyline and access to Windsor’s top attractions, such as Dieppe Gardens and Odette Sculpture Park. Ideal for walking, biking, or rollerblading, the trail seamlessly blends recreation and culture, with highlights including the iconic Great Canadian Flag plaza and art installations along the way.
Fun Fact: The trail is part of the Great Lakes Waterfront Trail, which stretches over 3,600 kilometers along Ontario’s Great Lakes, connecting diverse communities and natural landscapes.
8. Discover History at Fort Malden
Dive into Canada’s military past at Fort Malden National Historic Site, located just outside Windsor. A key defense point during the War of 1812, the fort is now a living history museum featuring reenactments, costumed interpreters, and preserved 19th-century buildings. Visitors can explore exhibits that detail the fort’s strategic role and learn about the lives of soldiers and settlers during this pivotal period.
Fun Fact: Fort Malden houses the only surviving barracks from the War of 1812 still intact in Canada, providing a rare glimpse into the era.
9. Gamble at Caesars Windsor Casino
For a night of entertainment and luxury, visit Caesars Windsor Casino, the largest in Canada. This world-class venue features a vast array of gaming options, including slots, poker, and table games, along with luxury accommodations, fine dining, and a stellar lineup of live performances. Even non-gamblers will enjoy the lively atmosphere and stunning waterfront views.
Fun Fact: Opened in 1994, Caesars Windsor was the first casino in Ontario and has since become a premier entertainment hub in the region.
10. Experience Windsor Sculpture Park
Windsor Sculpture Park offers a unique combination of contemporary art and natural beauty. With over 30 large-scale sculptures by internationally renowned artists, this open-air museum along the Detroit River provides a serene space for walking, relaxing, and reflecting. It’s a must-visit for art lovers and those looking to enjoy Windsor’s scenic riverside.
Fun Fact: One of the park’s standout pieces is “The Eve’s Apple” by Edwina Sandys, Winston Churchill’s granddaughter, which explores themes of temptation and human nature.
11. Visit Olde Walkerville
Discover Olde Walkerville, Windsor’s historic neighborhood that combines rich heritage with modern flair. Originally established by Hiram Walker, founder of Canadian Club Whisky, this area features grand architecture, wide tree-lined streets, and stately homes reminiscent of European villages. Today, Olde Walkerville is a lively hub of boutique shops, cafes, and trendy pubs. Don’t miss the chance to tour the Hiram Walker & Sons Distillery, where you can learn about the history of Canadian whisky production.
Fun Fact: Olde Walkerville’s layout mimics European villages, with spacious boulevards and a walkable charm reflecting its early 20th-century roots.
12. Tour the John R. Park Homestead
Step back in time at the John R. Park Homestead, a beautifully restored 1850s conservation site that offers a vivid look at pioneer life in rural Ontario. Visitors can explore the historic homestead, complete with heritage gardens, and participate in hands-on demonstrations like blacksmithing and traditional cooking. It’s a family-friendly spot where history truly comes alive through interactive experiences and costumed re-enactors.
Fun Fact: Built by John and Amelia Park, this homestead is one of Ontario’s few surviving pioneer homes, offering an authentic glimpse into life in the 19th century.
13. Attend a Festival
Windsor’s lively festivals bring the city’s vibrant culture to life year-round. From the Windsor International Film Festival (WIFF), showcasing independent films and attracting cinephiles nationwide, to Bluesfest Windsor, one of Canada’s largest blues festivals, there’s always something to celebrate. These events provide an ideal opportunity to experience Windsor’s diverse art, music, and food scenes while mingling with friendly locals.
Fun Fact: WIFF, Canada’s largest volunteer-run film festival, has been a cultural highlight since 2005, drawing filmmakers and movie enthusiasts from all over the world.
Conclusion
Windsor, Canada, is a hidden gem that blends its historical charm with modern vibrancy. Whether you’re strolling through the serene Dieppe Gardens, exploring the art-filled Sculpture Park, or sipping a glass of wine at a local vineyard, Windsor offers something for every traveler.
It’s a city where stories are told through its historic streets, celebrated through its lively festivals, and preserved in its beautiful landmarks. Windsor’s quiet allure and heartfelt hospitality leave a lasting impression, making it a destination worth revisiting again and again.
Planning to visit? Karta has some amazing offers on Windsor vacation rentals for you.
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.
