What You Need to Know About Cycling in Windsor Essex Pelee Island

Windsor Essex is an ideal part of Ontario to explore from the seat of your saddle. Whether you’re looking to cruise through historic towns, pop into breweries or wineries, or simply take in the serenity of the outdoors, you’ll undoubtedly find it here.

Windsor Essex Cycling — Pausing for a photo along the Rt. Honourable Herb Gray Parkway Trail, part of The Parkway Trail

In recent years, it seems to me that we’ve begun to look around Ontario and recognize that this is a mighty fine place to be a cyclist. Part of that charge is being led by forward thinking tourism boards who are laying out routes that enable people like myself to not only take in the scenery and the natural surroundings, but also to visit the restaurants, small businesses and sites that are, in essence, the lifeblood of the region.

Windsor Essex Pelee Island has done a particularly good job of just that in the establishment of their Cycle Tourism Map. They’ve essentially created six routes that showcase six unique ways to engage with and appreciate the region.

Don’t be scared to use the map as inspiration, but lean into the experiences that suit you best. For example, perhaps you might want to focus on Windsor’s brewery scene, spend some extra time exploring Kingsville, take in the sights and sounds of Amherstburg, or even to use cycling as a delightful excuse to spend a few days on Pelee Island.

Below, I’m going give you an overview of the routes that Windsor Essex Pelee Island has laid out, ultimately with the intention on inspiring you to throw your bike on or in your vehicle, and head this way. As Tourism Windsor Essex Pelee (TWEPI) itself notes, “Windsor Essex is a cyclist’s dream, with miles of trails to explore and enjoy.”

Which Cycling Trail in the Windsor Essex Pelee Island Should You Ride?

I’ve ridden a ton around Ontario, and I do think that this region has some excellent cycling to be had - especially considering the diversity of riding on offer. It’s everything from urban riding to rail trails, island cruising to cycling bridges over freeways.

The Windsor Riverfront Trail

This is a very easy place to start if you’re looking for an introduction to cycling in the region. It’s 34 kilometres in total, and most of it is very nicely paved and maintained. The trail is centred around the Windsor Riverfront and the Gantachio Trail (8 kilometres of scenic trails that connect Windsor to Tecumseh).

34 kilometres may sound like a fair bit, but if you’re tackling that over a half day or full day, it’s not bad at all. There’s a few spots that I’d suggest taking a moment to soak it all in. Firstly, when you’re riding along the downtown waterfront, take a moment to appreciate the Detroit skyline, and also take note of the Windsor Sculpture Garden which consists of over 30 large sculptures that are strewn about this “museum without walls.”

You’re going to want to stop to snap a shot of the Ambassador Bridge as well. Fun fact - you’ll be looking at the busiest international border crossing on the continent.

However you end up approaching the ride, you’d be wise to explore two Windsor neighbourhoods in particular. The first is Walkerville, and you’re in luck because I’ve written a guide to Walkerville! It’s a historic neighbourhood teeming with good restaurants, bars, art, and a brewery and distillery or two.

The other neighbourhood that I love exploring is none other than Ford City. It’s an up-and-coming neighbourhood with some genuinely intriguing small businesses that are shaping the area. And wouldn’t you know it, I’ve written a guide to Ford City on my sister site, Ultimate Ontario.

There’s plenty to explore in Windsor, so I’d recommend staying the night. If you like to roll the dice, don’t forget that Caesar’s Windsor is right in the heart of the city. My brother and I stayed there one weekend when we were doing a two city tour of Windsor and Detroit, and we certainly didn’t regret it.

The Wine Trail

The Wine Trail offers an easy 41 kilometres of riding, largely along the Lake Erie North Shore, which is where EPIC (Essex Pelee Island Coast) Wine Country is located. This is the up-and-coming wine region in the province.

For the most part, you’ll be bopping along Country Road 50 as you explore. Believe it or not, EPIC Wine Country now boasts almost 20 wineries, and many of the wineries are producing some world-class wines nowadays.

Part of the secret to this wine region is that this is the most southern shore of Canada, so the grapes are getting quite a bit more sun, and that helps a fair bit, especially if you’re trying to produce some bold reds. I’d research which wineries you want to visit beforehand (here’s an article we put together on EPIC Wine Country), then plan your route accordingly.

If wine just isn’t your thing, that’s fine as well. You can, instead, take in the scenic surroundings and perhaps spend more of your time at the John R. Park Homestead and Conservation Area or at the Serenity Lavender Farm.

The Parkway Trail

This is the trail in the area that I rode most recently, and it’s a great ride. It comes in at 67 kilometres, but it’s quite a flat ride overall, and one that I didn’t find too taxing. I was able to tackle it in an afternoon, more or less.

Basically, you’re taking the Rt. Honourable Herb Gray Parkway Trail to the Chrysler Canada Greenway Trail, popping into Essex, and then looping back up towards Windsor, but more specifically the Ojibway Prairie Provincial Nature Reserve.

I loved riding on the Herb Gray Parkway because it’s an example of some pretty unique urban riding. The trail is connected by bridges that extend over roads and highways, but ultimately get you where you’re going. It was interesting to be so close to traffic, and yet not have to worry about it all.

If you’re starting from the Ojibway Prairie Complex, it’s worth noting that Malden Park is just down the road, and it actually has the highest hill in Essex County that offers views of both Windsor and Detroit.

The Chrysler Greenway Trail was scenic as can be and offers 50 kilometres of uninterrupted riding, down paths that have lush trees and foliage on either side of you.

If you’re planning to stop in Essex, Windsor Essex Tourism notes that “Essex has a colourful history including explosions and inventions that are depicted in the towns’ outdoor gallery of murals. Take a self-guided tour of the thirteen large-scale murals and several Bell-Box murals. Be sure to visit the Spitfire Memorial, a replica of an Mk IX Spitfire painted to look exactly like the one Essex native Jerry Billing flew on D-Day. The memorial is located near the historic Essex Train Station.”

The Boblo Trail

This is a 61 kilometre route, 22 of which are spent on the Cypher Systems Greenway Trail. The reason that matters is because that trail will lead you to Amherstburg, which is one of the most charming towns in the province. So much so, in fact, that I wrote a full article on Amherstburg for Ultimate Ontario.

The Cypher Systems Greenway Trail is a classic example of an Ontario cycling rail trail, so you won’t be contending with traffic here.

In terms of exploration, I’d recommend Holiday Beach, Colchester Beach, as well as taking a peek at Colchester Harbour. For what it’s worth, many people feel as if Colchester Beach may be the more picturesque beach in the whole region.

The Pelee Trails

We visited Pelee Island a few years back, and it was love at first sight. Seriously - I think there’s still a piece of my heart there. What’s fun about cycling on Pelee Island is that you can bike the entire 42 square kilometres of Pelee Island. Since you have to take a ferry over and all of that, though, I’d suggest that you at least spend the weekend there if you can.

This route is the most ambitious, coming in at 96 kilometres, but it’s also, in my opinion, the most remarkable. You kick things off in Kingsville, Canada’s southernmost town and one that’s criminally underrated. Then, it’s on to Point Pelee National Park where you can hop on a trail that takes you into the forest, and out to the southernmost tip of the Canadian mainland. Have your camera ready here!

If, somehow, you didn’t get your nature fix in Point Pelee, you’re sure to satisfy it with your stop in Hillman Marsh Conservation Area. I’d then aim to grab a bite in Leamington, then hop on the 90 minute ferry over to Pelee Island. Again, I’d likely plan to stay the night there. It probably makes the most sense to spend day one with the cycling listed above taking place on the mainland, and then doing a full second day of cycling on Pelee Island.

You can use the article that I’ve linked up at the top here to plan your adventure, but note that it’s basically a cyclist’s dream come true. I strongly feel that every Ontarian should visit Pelee Island at some point in their lives, and why not experience it from the saddle of your preferred bike?

The Lakeside Trails

If you’re looking to be by the water as much as possible, this is a good route to look towards. It comes in at 55 kilometres, but most of the ride is within a stone’s throw of the water. If you want to double down on the water adventure, you can even end your ride with a little paddle boarding at Urban Surf Co., something I wrote about recently in an outdoor adventure article I put together for the region.

The real highlight of this route is what you’ll see as you’re biking along Lake St. Clair - namely gorgeous homes and lighthouses galore. You can stop at Lighthouse Cove and Belle River Lighthouse in particular if you’re keen to snap a few good photos along the way (though that won’t be altogether too hard on this route).

If you want an extended break, consider spending some time exploring the town of Tecumseh. You can even plan the route so that you stop for lunch. Personally, I’d recommend grabbing a pint and a bite at Frank Brewing Company, but if you’re trying to get something light, then you may want to visit Carrots n’ Dates.

That’s a Wrap on Windsor Essex Cycling

Each of these routes offers something different, and thus I’d recommend taking the time to tackle them all when you can. TWEPI has actually created a brilliant little cycling map that’s 9 pages in all and goes even more in-depth on each route. If you can, print it before heading this way. I used it during my explorations and it was invaluable.

This is a region that’s known for a lot of things, but it’s only just now getting a reputation as a premiere cycling destination in this province, and that’s a reputation that’s very much well deserved.

We want to humbly thank Tourism Windsor Essex Pelee Island for hosting us as media. All opinions are completely our own.

If you appreciated this article, you’ll love our newsletter, as well as our Facebook group! Feel free to join, all are welcome. If you’ve got any questions or comments, add them below, and I’ll be sure to get back to you.