Windsor-Essex has so many great trails to explore while walking or cycling. Here are 9 of our favourites that should lure you out into the sunshine for a great day of exploring and fun.



Let’s get this one out of the way quickly. An extremely popular, casual and scenic trail that winds down over 5km of Windsor, Ontario’s, waterfront. Locals and visitors alike love it. One one end is North America’s largest distillery, on the other end is a historic and iconic bridge connecting Canada to the USA.

Along with the beautiful view of the Detroit, Michigan, skyline, you’ll pass the Bert Weeks Memorial Fountain, a ginormous Canadian flag and an outdoor sculpture garden. You can also catch some stunning sunsets.



It’s hard to believe this unique woodland is located in an urban centre. Enter this natural area and feel the stresses of life melt away. Located in the City of Windsor, Devonwood features more than 4.5 kilometres of trails promote healthy and active living for people of all ages.

Perhaps no other woodland in Canada supports a greater diversity of oak trees: eight species of oak are found in this urban forest. Can you identify all eight while riding through? Stay alert as you walk the extensive trail system winding through this 38 hectare forest. You may also see Eastern Screech Owls, Long Eared Owls and Little Brown Bats. A great urban spot for bird watching.



Not necessarily a trail, but, a great ride for wine lovers who are a little more comfortable cycling on the road. County Rd. 50 huges the Lake Erie shoreline through 3 municipalities: Amherstburg, Essex, and Kingsville. You’ll have the opportunity to visit 7 wineries, do some antiquing, stop at some of the many farm stands and just enjoy a great ride.

If you’re more into guided tours, jump in on the award winning Wine Trail Ride cycling tour. It’ll take you along County Rd. 50 and more while you drink wine and enjoy a gluttony of food.



The approximately 17 kilometre multi-use trail is the first trail that has been incorporated into a major provincial highway project in Ontario. The Herbi Gray Parkway Trail network features a continuous multi-use lit pathway, with bridges and tunnels that allow pedestrians and cyclists to travel the length of the parkway without encountering vehicles.

Rest areas and interpretive signs are also located where there are features of interest and to provide users a spot to rest and enjoy their surroundings. Signage along the trails includes information about the parkway, regional and cultural heritage, First Nation culture and history, and the special natural areas.



Black Oak Heritage Park supports one of the finest stands of black oak in Southwestern Ontario and is home to such nesting birds as Scarlet Tanager, Rose-breasted Grosbeak, Eastern Bluebird and Cooper’s Hawk. Many of the native plants at Black Oak Heritage Park are extremely rare elsewhere in Canada.

Black Oak Park is part of the Ojibway Prairie Complex, which itself is beautiful to walk through.The complex includes Ojibway Park, Tallgrass Prairie Heritage Park, Spring Garden Natural Area and Ojibway Prairie Provinical Nature Reserve.

The size is small, being just two kilometres of marked trails with opportunities for passive recreational activities such as hiking, bird-watching, photography and leisure cycling, but, it’s still beautiful to go through.



The Great Waterfront Trail brings you across Ontario by bike.
The Great Waterfront Trail brings you across Ontario by bike.

Windsor- Essex County is part of the 3600km Great Lakes Waterfront Trail. The trail is a foundational part of a bigger strategy to protect and regenerate our Great Lakes by connecting 155 communities and ecosystems along the waterfront. In fact, County Rd. 50 is part of it.

The Great Lakes Waterfront Trail portion in Windsor-Essex is rich in natural areas, including a Point Pelee National Park, Fort Malden National Historic Site, 24 conservation and protected areas, 27 municipal parks, and 37 beaches. Did we mention lots of restaurants and wineries, too?
The Windsor Essex Pelee Island section is 186 Kilometres (26km is off road—other sections use roadways with shoulders and quiet streets).  You can complete a loop by using the Trans Canada Trail from Leamington to Lakeshore (34 km) or the Chrysler Greenway from Kingsville to Windsor



The 50km Chrysler Canada Greenway is a rail-to-trail perfect for hiking, biking, running, birding and cross country skiing, and in some areas, horseback riding.

With entry points across Essex County, it’s a great way to avoid vehicle traffic and connect to municipalities like Amherstburg, Essex, Kingsville and Leamington. It joins 25 otherwise separate natural areas, including regional Environmentally Significant Areas and provincial Areas of Natural and scientific interest, and three watersheds.



Ganatchio Trail is named after the Indian word for Lake St.Clair. The trail is 8km long and features a two-lane paved pathway which is perfect for a leisurely stroll or bike ride with the family, rollerblading, and jogging.

There is also a 3.25km extension called the Rotary-Ganatchio Little River Extension.



With 12km of bike trails and the 9km roadway, biking is a great way to explore Point Pelee National Park. The trails are well groomed and accessible for most riders.

One of their trails is the topsy-turvy Centennial Hike and Bike trail! This 6km trail whisks you through different habitats – from marsh to dry forest, past savannah, swamp forest and beach and is a great way to experience the park.

If you don’t feel like lugging your bike to the park, head to Northwest Beach on Saturdays and Sundays and you can rent a bike. We recommend booking them in advance.

You should also go explore the Marsh Boardwalk There’s event Marsh Boardwalk with observation tower and telescopes and see if you can catch a glimpse of the beavers hard at work.