Kick off your cycling adventure at the Ojibway Prairie Complex, a 350-hectare natural haven protecting one of Canada’s last tallgrass prairies and oak savannahs. Cyclists can explore paved and crushed-stone trails that wind through forests, ponds, and prairie habitats, all while spotting rare plants, butterflies, and over 160 species of birds. The Ojibway Nature Centre offers interpretive exhibits, maps, and educational programs highlighting the area’s ecology and Indigenous heritage. It’s a perfect combination of cycling, wildlife viewing, and hands-on nature learning in the heart of Windsor Essex.

Just down the road, Malden Park invites riders to climb Essex County’s highest hill, with panoramic views of downtown Windsor, Detroit, and the Gordie Howe International Bridge from the park’s new lookout area. Paved and wood-chipped trails wind through the 175-acre park, offering both gentle loops and more challenging hills for cyclists of all skill levels.

From Malden Park, hop onto the Rt. Hon. Herb Gray Parkway Trail, a 17-kilometre multi-use route stretching to Howard Road at Hwy 401. Bridges, tunnels, and lit pathways allow cyclists to ride safely without encountering vehicles, while interpretive signage shares the parkway’s design, regional culture, First Nations history, and surrounding natural areas.

Trail connections expand your adventure. Head west to the LaSalle Trail System, a scenic network of trails weaving through forests, open fields, and wetlands. Cyclists will enjoy gentle curves, gradual hills, and multi-use paths suitable for all abilities. Along the way, stop at parks, waterways, and natural areas for picnics, wildlife spotting, or photos. Consider River Canard Canoe Co. for renting a canoe or kayak and enjoying a scenic paddle along the peaceful River Canard, offering a unique way to combine cycling with water-based adventure and local exploration.

Pedal south to the Chrysler Canada Greenway Trail, a 50-kilometre route from Tecumseh to Kingsville, forming the southernmost link of the Trans Canada Trail.

Along the way, explore the Town of Essex, rich in history and culture. Discover the outdoor mural gallery featuring thirteen large-scale murals and several Bell-Box murals, or visit the Spitfire Memorial, a replica Mk IX Spitfire honoring Essex native Jerry Billing on D-Day. To get there, take the Cypher Systems Greenway Trail, a scenic multi-use pathway featuring smooth, paved surfaces, gentle curves, and connections to parks and neighbouring communities.

With its mix of natural beauty, connected trails, and cultural landmarks, the Parkway Trail offers cyclists an immersive experience of Windsor Essex’s outdoor adventures, scenic landscapes, and local heritage.