The best road cycling routes around Windsor
4.5
(22)
569
riders
15
rides
Road cycling around Windsor offers a diverse landscape characterized by extensive waterfront trails, urban parks, and agricultural lands. The region features a network of paved pathways, including sections of the Trans Canada Trail, providing varied cycling experiences. While generally flat, some areas like Malden Park offer gentle hills, making the terrain accessible for different skill levels. The city's commitment to cycling infrastructure ensures well-maintained routes through both natural and developed areas.
Best road cycling routes around Windsor
- The most popular…
Last updated: May 4, 2026
5.0
(1)
32
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
22
riders
37.1km
01:37
70m
70m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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5.0
(1)
20
riders
63.6km
02:36
110m
110m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
29
riders
23.8km
00:55
30m
30m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
3.0
(1)
21
riders
49.2km
02:03
90m
90m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Windsor
Tips from the Community
Assumption Park along Windsor’s riverfront is home to the Windsor Sculpture Park’s unique collection of contemporary outdoor art. There are over 35 large-scale sculptures by renowned international artists, set against views of the Detroit River and the Ambassador Bridge. With its blend of public art, walking paths, and peaceful waterfront atmosphere, it’s a favourite spot for locals and visitors to relax, explore and enjoy the views.
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Great Western Park is a lovely green space that stretches along the Detroit River, with expansive views of passing freighters and the U.S. shoreline. There is a paved multi-use trail that connects to the Riverfront Trail network, making it a popular destination for walkers and cyclists. With its mature trees, benches, and beautiful river views, it’s a peaceful spot to relax or watch the sunset over the water.
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The Ambassador Bridge took two and a half years to build and opened on November 15, 1929. At the time, it was the longest suspension bridge in the world. After almost 100 years of service, it is finally being relieved by another bridge further upstream. While there is a toll to use the bridge, a photo taken at night with the lights is almost priceless! 😀
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Paradoxically, the most beautiful view in Windsor at night is the view of Detroit in the USA. By day, it's a big city like (almost) any other, but at night it's quite impressive. Here you can see the American penchant for prestige, showmanship, and glitz. In its heyday, Detroit was the headquarters of many car manufacturers. Anyone who can and wants to should try crossing the bridge. The cities are connected by a bridge and a tunnel. The one-way trip to the USA by car currently costs CA 11 via the bridge.
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Frequently Asked Questions
How many road cycling routes are available in the Windsor area?
There are over 15 road cycling routes around Windsor documented on komoot, offering a variety of experiences for different skill levels. These routes range from easy, shorter rides to more moderate, longer excursions.
What kind of terrain can I expect on road cycling routes around Windsor?
Windsor's road cycling routes are generally flat, making them accessible for many cyclists. However, some areas, like Malden Park, offer gentle hills for those seeking a bit more challenge. You'll find extensive paved pathways, waterfront trails, and routes through agricultural lands.
Are there any easy road cycling routes suitable for beginners or families in Windsor?
Yes, Windsor offers several easy road cycling routes. An example is the St. Clair College Prairie ESA loop from Sandwich, which is just over 18 km and has minimal elevation gain, making it a great option for a relaxed ride. The Windsor Riverfront Trail is also ideal for leisurely rides.
Where can I find scenic viewpoints or landmarks along the road cycling routes?
Many routes offer scenic views, especially along the Detroit River waterfront. You can enjoy views of the Detroit skyline from the Windsor Riverfront Trail. Notable landmarks and viewpoints include the Gateway to Freedom Monument and the Detroit Riverwalk Viewpoint. The William G. Milliken State Park also offers great vistas.
Are there any longer road cycling routes for more experienced riders?
Absolutely. For longer rides, consider routes like the Puce River – Ruscom River loop from Tecumseh Mall Bus Terminal, which covers over 63 km through rural and riverine landscapes. The Chrysler Canada Greenway also offers nearly 50 km of multi-use trail for extended rides.
What do other road cyclists say about the routes in Windsor?
The road cycling routes in Windsor are highly regarded by the komoot community, with an average rating of 4.4 out of 5 stars from over 10 reviews. Cyclists often praise the well-maintained pathways, scenic waterfronts, and the variety of routes available for different skill levels.
Can I find circular road cycling routes in the Windsor area?
Yes, many of the road cycling routes around Windsor are designed as loops, allowing you to start and end at the same point. For instance, the Assumption Park loop from Windsor is a popular circular route along the Detroit River.
Are there road cycling routes that pass through natural areas or conservation parks?
Yes, Windsor and Essex County are rich in natural beauty. The Chrysler Canada Greenway connects natural areas and agricultural lands. You can also explore areas like the Ojibway Prairie Complex, which features tallgrass prairie and oak savanna habitats, or the Devonwood Conservation Area with its woodland trails.
Are there opportunities to combine road cycling with exploring local attractions like wineries?
The Essex Pelee Island Coast is known for its award-winning wineries, and the Wine Trail offers a unique way to explore them by bike. While specific komoot road cycling routes may not directly feature winery stops, the regional network allows for such detours.
What are some notable parks or green spaces accessible by road bike in Windsor?
Windsor boasts several parks and green spaces ideal for cyclists. The Windsor Riverfront Trail connects various parks like Dieppe Gardens and the Windsor Sculpture Park. Jackson Park is known for its extensive plant collections, and Malden Park offers naturalized trails and the highest hill in Essex County.
Are there any car-free cycling options in the Windsor region?
Yes, the Herb Gray Parkway Trail is a notable 17-kilometer multi-use trail that offers a dedicated car-free cycling experience. Additionally, sections of the Windsor Riverfront Trail and the Ganatchio Trail provide safe, paved pathways away from vehicle traffic.
What is the best time of year for road cycling in Windsor?
While specific seasonal considerations can vary, the spring, summer, and fall months generally offer the most pleasant conditions for road cycling in Windsor. These seasons provide comfortable temperatures and vibrant natural scenery, making for an enjoyable ride.
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