Windsor Kingsville Essex Tour

Multiday Trip – 3 Days / 2 Nights

Total Distance: 130km  

The Ride: Pedal into the Heart of Southern Ontario’s Wine Country on this 3-day cycling adventure, beginning and ending in Windsor! Enjoy scenic rural roads into the heart of Canada’s southernmost wine region. Follow glistening Lake Erie and Detroit River shorelines with panoramic views of rich agricultural lands. Refuel with local produce at farm stands you’ll pass along the way. Ride down the Chrysler Canada Greenway through charming towns, natural areas, beaches, historical buildings and culinary offerings you have to taste to believe.

Experience Level: Moderate to Experienced: This route is suitable for cyclists with experience and comfort riding on roads with some vehicle traffic. Some trails are best suited to hybrid bikes, although road bikes can also be used. The Lake Erie portion of the Great Lakes Waterfront Trail is an on-road route. The majority of the route is along rural roads with limited shops for refreshments. Cyclists should bring extra water and snacks.

View digital route of tour –

Day 1: Windsor to Kingsville – 55km

Area services along this section of the route: Accommodations, cafés, restaurants, grocery stores, shopping, banking, bike shops, attractions, wineries and trails.

Follow routing out of Windsor and connect to the Chrysler Canada Greenway, a crushed stone rail trail. Once connected to the Chrysler Canada Greenway services are limited until you arrive in Harrow. Take extra water and other refreshments as needed. Restaurants, grocery stores, shopping, banking, wineries and trails are available in Harrow. Cyclists wanting to do a riding-wine tour can easily visit wineries in Harrow and close to the trail from this point forward, including: Colio Estate Wines, Cooper’s Hawk Vineyards and Black Bear Farms of Ontario Estate Winery Continue on Chrysler Canada Greenway until your ride for the day ends in Kingsville, the southernmost downtown in Canada. Enjoy the area’s rich agricultural history and Victorian-era architecture.

Day 2: Kingsville to Amherstburg – 44km

Area services along this section of the route: Accommodations, cafés, restaurants, grocery stores, shopping, banking, attractions, wineries and trails.

Ride west on Heritage Drive / County Road 50, part of the signed Great Lakes Waterfront Trail (road cycling), a scenic route dotted with wineries, open and ready for tours and tastings, and rich farmlands running parallel to the shores of Lake Erie with numerous beach access points. Turn onto County Road 20, west towards the shoreline of the Detroit River and continue to Amherstburg, your final destination for the day. This historic town on the banks of the Detroit River boasts unique, century-old buildings and a quaint waterfront setting. Can’t-miss historic sites include Fort Malden National Historic and Parks Canada Site, a fortress that’s seen War of 1812 battles, and the North American Black Historical Museum, which showcases the history of the Underground Railroad and freedom for Black Africans escaping slavery in America.

Day 3: Amherstburg to Windsor – 30km

Area services along this section of the route: Accommodations, cafés, restaurants, grocery stores, shopping, banking, bike shops, attractions, wineries and trails.

Follow the recommended road routing and signs for the Waterfront Trail. Go along ThomasStreet /2nd Concession for a quieter ride. Stop for a refreshment in LaSalle to gear up for the last leg of the trip. Continue to follow recommended routing and signs for the Waterfront Trail. From the Ambassador Bridge, ride along the paved, multi-use Roy A. Battagello River Walk/Waterfront Trail to downtown, near Ouellette Avenue in the central waterfront area of your final destination, Windsor.

Additional Information

Getting To/From Start: Parking is available at accommodations and Windsor’s municipal parking lots or garages. Multiday parking passes are available. Bike transportation is available on VIA Rail trains with baggage service. Bike rentals are available in Windsor at City Cyclery or Wine Trail Rides/Windsor Eats.

Visitor Information: Use below to find out more about ride areas and plan an extra day or two to see more.


As part of Canada’s 150th celebrations in 2017, Ontario 150 Celebrate by Bike connected fifteen communities across Ontario through cycling. Ride itineraries, events and cycling education in Bike Friendly Communities and Ontario By Bike ride destinations were developed and hosted to take advantage of the iconic Greenbelt Route and Great Lakes Waterfront Trail to strengthen communities and create cycling itineraries as a permanent legacy of Ontario 150. This initiative was a collaborative partnership between the Waterfront Regeneration Trust, the Friends of the Greenbelt FoundationOntario By Bike, and Share the Road Cycilng Coalition, building on two decades of investment in cycling infrastructure in Ontario. Check out the 15 legacy ride itineraries, and make plans to get out there to explore more of Ontario By Bike.

Ontario 150 Celebrate by bike