Taste of Windsor Essex

Celebrate 25 years of trail-building and work to protect and connect our Great Lakes and St. Lawrence waterfront with the Summer of Adventure!

The Windsor Essex peninsula is Ontario’s southern heartland, being on the same latitude as northern California and southern Italy. 

What you’ll love:  Stunning shoreline views, picnics at award-winning wineries, farm fields, Carolinian woodlands, exceptional beaches, historic sites, fantastic birding, beautiful waterfront parks and gardens. Point Pelee National Park’s UNESCO designated wetland and gorgeous beach. 

Terrain—Easy terrain, flat paved shouldered roads, firm limestone or asphalt paths, some quiet streets.

Don’t want to ride on the road?  Hikers and people who prefer to cycle on dedicated paths will enjoy:

  • Chrysler Greenway/Trans Canada TrailMap.  Kingsville Train Station to Ceasars Windsor Community Entrance 32 km.  Park at the Caesars Windsor Community Entrance (15403 Essex 8OldcastleON N0R 1L0Canada), seasonal portable washroom facilities available and ride to Harrow or the Kingsville Train Station Community Entrance (169 Lansdowne Ave, KingsvilleON N9Y 1L7Canada). Restroom facilities are available. This historically and architecturally significant building has been magnificently restored and is home to the renowned Mettawas Station Mediterranean Restaurant.
  • Hon Herb Gray Parkway Trail/Trans Canada TrailMap.   17 km multi-use trail extends from Malden Road (in Windsor) in the west to County Road 9 in LaSalle in the east with bridges and tunnels that allow pedestrians and cyclists to travel the length of the parkway without encountering vehicles. Rest areas and interpretive signs include information about the parkway, regional and cultural heritage, First Nation culture and history, and the special natural areas.
  • Windsor City Riverfront Trail/Great Lakes Waterfront Trail – 5km of trail through a series of waterfront parks. Several parking lots available, for example: 533 Riverside Dr. East, Dieppe Gardens at 78 Riverside Dr. West.

The Taste of Essex–Ride

Distance—2-day, 140 km loop from Kingsville to Windsor and back and can extend your adventure by heading to Leamington and Point Pelee National Park.

Time--While this tour can be completed in two days, we recommend completing this route in 3-4 in order to truly experience and enjoy the area. You can begin in Leamington, Kingsville or Windsor. We suggest using Leamington or Kingsville as your base camp and ask your accommodation provider for permission to park your car for a couple of days during your ride.

Ride with GPS Map: https://ridewithgps.com/routes/32762142

Essex County-wide Active Transportation Cycling Maphttps://www.countyofessex.ca/en/discover-the-county/cwats-maps.aspx. An excellent printed map is also available at local recreation centers, municipal offices, and libraries.

Day 1 – 80 km on the Great Lakes Waterfront Trail from Kingsville to Windsor. 

Paved shoulders along County Road 50 are part of Essex County’s visionary County Wide Active Transportation System (CWATS). Over the next 15 years, CWATS will link seven local municipalities with an active transportation network spanning some 800 km–and a substantial part of the network is part of the Great Lakes Waterfront Trail.

Just 5 km in and we see our first beach at Cedar Beach Conservation Area (1031 Heritage Rd). Though closed during Covid, it offers a breathtaking view of Lake Erie. It is a popular sandy spot for swimming and fishing on Lake Erie at the mouth of Cedar Creek. Launching from the dock at Cedar Creek, just off Arner Townline (County Road 23), kayakers paddle down the Creek to Lake Erie–usually takes an hour.

10 km   Return to the 19th Century as you walk around the restored home and farm buildings of John and Amelia Park at the John R. Park Homestead.

This is award-winning wine country. Be sure to do some sampling.

Windsor Essex has the longest growing season in Canada. So it is no surprise the important role of agriculture to the regional economy.

16km — North 42 Estate Winery (130 County Rd 50, Colchester ON).

Just down the road from North 42, you’ll find Garfield’s (1 County 50 Rd West, Harrow) has a front patio and back yard patio for guests to enjoy a meal and break.

Colchester Harbour Park and Beach–the Beach is closed during Covid.

24 km– Sprucewood Shores Estate Winery–Ontario’s only beachfront winery. Enjoy sampling the wine or arrange for a picnic lunch on the grounds.

Turn into Holiday Beach Conservation Area. Holiday Beach Conservation Area has large shady picnic areas, a playground, nature trails, a boardwalk, sandy beach for swimming, and a three-story observation tower.

48 km — Amherstburg has a stunning waterfront steeped in history. Visit King’s Navy Yard Park on Dalhousie St. If you are still looking for food, try Waterfront Ice Cream. Historic Fort Malden, the location of a historic meeting between Major General Sir Isaac Brock and Shawnee Chief Tecumseh is open on weekends.

50 km — St Joesph Church at River Canard, LaSalle. The Trail crosses the River and continues north on Malden Road (CR 3).

Pass the entrance to the Hon. Herb Gray Parkway on the right–you’ll get a taste of that wonderful new facility tomorrow. The Trail turns left into Malden Park and here is co-designated as part of the Great Trail/Trans Canada Trail.

A view of the Ambassador Bridge connecting Canada to the US in the Windsor Sculpture Park.

Stunning views across the Detriot River to the US.

There are many accommodation options in Windsor–many on the waterfront, for example, Best Western Plus Waterfront Hotel. Old Sandwich Towne– is a great place to head for beer or dinner. We love Rock Bottom Bar and Grill (3236 Sandwich St, Windsor)

Day 2 – Windsor to Kingsville (60 km)

After a short backtrack along the Great Lakes Waterfront Trail, you’ll follow the Chrysler Greenway / Great Trail south to Harrow and then Kingsville.

Located within Ambassador and Centennial Parks, the Windsor Sculpture Park treats you to 31 internationally recognized works of contemporary art. We can thank the generosity of Mr. and Mrs. Louis Odette and the P & L Odette Foundation for the collection, which is at the same time, whimsical and thoughtful. The sculpture in the photo is Eve’s Apple by Edwina Sandys. Learn more and get a peek at the collection.

Pick up the spectacular Herb Parkway Trail just south of Malden Road. Thank you MTO for incorporating this ideal trail system as part of a major highway extension. The Trail is loaded with beautiful interpretation panels that share the history of the area including the Indigenous Seven Grandfather Teachings.

The Hon. Herb Gray Parkway Trail is also part of the Trans Canada Trail/Great Trail.

You exit the Herb Gray Parkway Trail at South Talbot and ride on the road for about 0.5 km to the start of the Rotary Centennial Hub. This is the beginning of a 3 km dedicated trail that connects you to the Chrysler Greenway.

The Chrysler Greenway Trail is an easy, scenic ride. Just be sure to stop and take care when crossing roads that intersect with the Trail.

Pelee Island Winery is one of several wineries along the Greenway. Please check their website in advance to see how the pandemic is impacting operations.

Pleasant Valley Campground is located just south of the Trail in Kingsville. The restaurant is open if you want a meal. Only trailer camping is available during the pandemic.

Optional Day 3 – Ride (or drive) to Point Pelee National Park with serene views of the water, plenty of open trails and birding opportunities. Be sure to walk to the Tip. It is the southern point of the park and also the southernmost point of land in Canada.

Celebrate another great day on the Trail with an ice cream cone from Pelee Cone!


Looking for other ideas in Essex–download the Tourism Windsor Essex Pelee Island Cycle Tourism map for 354 km of loop cycling routes.

Download the Printed Maps:
Tourism Essex Windsor Pelee Island developed an excellent cycle tourism map for the region which offers several excellent riding itineraries in the area: https://visitwindsoressex.com/wp-content/uploads/2019/06/cyclingmapv3.pdf

Leamington to Windsor and Pelee Island- https://waterfronttrail.org/maps/leh-05-Essex-Windsor-Pelee.pdf
Map of Pelee Point National Park

Use our custom interactive Google map to check distances. And points of interest. https://waterfronttrail.org/map/interactive-map-2/

What to bring:
Don’t forget your sanitizer, snacks and water as facilities are not fully open. Please respect physical distancing protocols and call accommodations and facilities in advance to confirm hours.

Learn More About the Communities

Tourism Essex Windsor and Pelee Island (TWEPI)–has loads of information about accommodations, places to eat, guided outings.

WindsorEats–loads of information about where to eat including the ultimate list of patios to visit in Windsor.  Once restrictions related to Covid ease, check out their cycle and walking tours.

Essex County- https://www.essex.ca/en/discover/Cycling.aspx

Leamington-  https://www.leamington.ca/en/discover/festivalsandeventsthingstodo.aspx


Essex —https://www.tourismessex.ca/en/index.aspx




If you have more time:

Consider taking the ferry  to Pelee Island where you will find 28km of quiet on-road Waterfront Trail (some gravel), several nature sanctuaries and beaches. Reservations are required for all passengers including walk-on. Reservations may be made by calling 1-800-661-2220. Everyone must wear a mask on-board and no food will be served or is allowed on the ferry. http://www.ontarioferries.com/en/home/

Find out what’s open on Pelee Island during Covid