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3-Day Bike Adventure in Windsor Essex | Tour Recap & Itinerary

Windsor Essex

Exploring Essex County by bike

When the group of 35+ riders set off from Comber on the Saturday of the 2018 Labour Day long weekend here in Canada, it was already heating up and most knew it was bound to be scourcer. It didn’t take long for riders of the Essex Windsor Loop, an Ontario By Bike Ride and small group tour, to get right into the quiet countryside amongst the corn fields and wind turbines.

It certainly brought back memories for many returning riders who rode our Uxbridge Kawartha Rail Trail weekend in 2017. We stated in a previous blog post that that tour will go down in history as the hottest one. This one may have topped it and the turbines gave no reprieve.

This was the first time an Ontario By Bike Ride had been hosted in Essex County and the region delivered a wonderful cycling experience, leaving many of our ride participants with lasting memories and a desire to return.


Here’s the nitty gritty about the route:

  • Total Distance: 186km / 116 miles
  • Suggested Ride Time: 3 days, 2 nights
  • Experience Level: Moderate
  • Route Surfaces: Paved and unpaved multi-use trails. Road sections require caution, with no paved shoulders or cycling facilities.
  • Digital
  • Downloadable PDF Itinerary:

Day 1 – Comber to Windsor – 52km

The group set off from Comber Community Centre and headed north, quickly connecting to agricultural lands, towards the southern shores of Lake St. Clair. The views stretch on for days in Essex County, which is known for being relatively flat. It makes for a warm day with little coverage from trees, but also for a fun ride full of great views and easy riding with friends.


Connecting to the Great Lakes Waterfront Trail, we continued heading west towards the city of Windsor. The morning ride took us past sleepy cottage communities along Lake St. Clair into the community of Belle River. Our lunch spot for the day was at Lakeview Park West Beach & Marina and was a welcomed stop after a hot morning of riding with shaded picnic tables, washrooms, beach views and an ice cream vendor! Our boxed lunches were provided by Iron Kettle B&B in Comber. Certified as a FeastON culinary provider, as well as a certified bicycle friendly accommodation. Benjamin (the chef and proprietor) nailed it, leaving our guests more than satisfied and refueled for the afternoon ride.

Lakeview Park

In Belle River, we were met by Tom and Sue, founders of Share the Road – Essex County, an independent and unfunded, regional cycling advocacy group. Amazing people and great ride companions, they set off with the group heading west towards our next stop of the day, Urban Surf Co. Located along a river’s edge on the eastern end of Windsor, they serve up great smoothies and cool drinks and was the perfect spot to regroup and rest up on a hot day.

Urban Surf Co

Our final routing into Windsor included road riding along Riverside Drive, a portion of the Great Lakes Waterfront Trail, before connecting to the Ganatchio Trail, a paved off-road trail. After some additonal road riding, this route connected to the stunning Riverfront Trail along Windsor’s waterfront parklands with a stunning view across the Detroit River to ‘Motown’.

Riverfront Trail

Our hotel, the Best Western Plus, was located on Riverside Drive, a stone’s throw to the Riverfront Trail. A very bicycle friendly hotel, guests were allowed to roll their bikes right into the lobby and leave them in a secure conference room for the night (or bring the bikes up to their room). After a hot day, many enjoyed a swim in the pool and a visit to Craft Heads Brewing Company, the location for our group social that evening.

Day 2 – Windsor to Leamington – 73km

We started off with a ride along Riverfront Trail, heading southwest as we started our curve along the edge of the peninsula passing under the Ambassador Bridge. A short section of quiet city streets and park trails connected the group to the brand new and paved Herb Gray Parkway Trail, which runs adjacent to the Herb Gray Parkway a new highway in Windsor. An absolutely amazing path that criss-crosses above and below the highway for nearly 17km, taking our group southeast out of Windsor and connecting to the Chrysler Greenway Trail, a 48km crushed stone rail trail.

Chrysler Greenway Trail

Our 30km morning ride led us to our schedule break stop, the Essex County Steam and Gas Engine Museum. Volunteer led, the organizer’s opened up their doors just for our tour giving us an opportunity to cool down, refill water bottles and visit the amazing collection of agricultural machinery that worked the lands we rode through this weekend. After a short stop, the group set off to our lunch destination at Colio Estate Winery in Harrow. Located just off the trail, the winery was a perfect stop for lunch, with its covered pavillion and air conditioned tasting room. We were met again by Tom and Sue from Share the Road – Essex County, who took a group of riders south to ride on County Road 50 through one of Ontario’s emerging wine regions.

Colio Estates Winery

For many others, our afternoon ride continued along the rail trail through Kingsville and on to Leamington. After short stops in downtown Kingsville (a must if you’re riding in the area), Mettawas Station Restaurant (an amazing trail-side Mediterrean restaurant in a converted rail station) and Pelee Island Winery (another must visit, trail-side attraction), the group got in to Leamington late afternoon. After settling into our hotel for the evening, the certified bicycle friendly Quality Inn and Suites Leamington, riders headed off to local eateries, hungry from riding over 70km that day. Many made their way to the beaches of Lake Erie and Seacliff Park for an ice cream and to watch a sunset before calling it an evening.

Day 3 – Leamington to Comber – 61km

On the final day of riding, the group set off early to head south out of Leamington to Point Pelee National Park. A beautiful section of road riding into the park was made more enjoyable with frequent views of Lake Erie and marsh lands, as well as the tree-covered route through the park itself.

Point Pelee National Park road

A stop into the fantastic Visitor Centre and a trip down to ‘The Tip’ was a highlight for many, as was the walk out into the wetlands along a boardwalk.

Point Pelee National Park

The day continued with road riding back into Leamington and a picnic lunch in Rick Atkin Park where guest enjoyed views of the Pelee Island Ferry and Leamington waterfront. After lunch, riders began their ride north, through Leamington, connecting to the Trans Canada Trail that runs for 18km to Comber. While a little rocky at first, and with storm clouds approaching, only a few got caught in a shower before making it back to Comber Community Centre and the end destination for this 3-day tour.

Additional Visitor Information:

Use below to find out more about riding the area. Be sure to plan to stay an extra day or two to see more.

Getting To/From Start:
Comber is conveniently located just south of Hwy 401, on County Road 77 exit (#77) and is 35 minutes east of Windsor, 1.5 hours west of London.

Arriving Early / Staying Late:
Consider an overnight option at the certified bicycle friendly The Iron Kettle Bed & Breakfast in Comber or stay at other nearby Ontario By Bike Network accommodations in Windsor Essex or Chatham-Kent.

What a season!

We’ve wrapped up our small group tours for 2018, having ridden over 500km with more than 125 cyclists in 4 amazing destinations across Ontario! Visit our Ontario By Bike Ride page below to download one of the self-guided itineraries and ride any one of our past routes on your own!

Our self-guided, supported tours incorporate fun, recreational routes, as much trail as possible and all the services that allow guests to ride at their own pace and find all the hidden gems Ontario destinations have to offer. With a maximum of 35 cyclists, these value priced ride weekends do sell out early. Don’t miss out! Sign up to our enewsletter to recieve first notice of our 2019 tour dates and destinations, which will be announced in February!


Consider joining us on an Ontario By Bike Ride and small group tour in 2019!

Published On: September 25, 2018Categories: Destinations, Ontario's Southwest

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