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2018 Cycling In Ontario Guide

Cycling Adventures Await in Canada’s Deep South

Windsor Essex

Hand-crafted, ride-ready routes in Canada's Deep South. Enjoy trails, wineries and the burgeoning food and drink scene happening in Windsor Essex - by bike of course!


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Ontario By Bike Ride Essex Windsor September 2018

Essex County Self-Guided Winery Bicycle Tour | Ontario By Bike

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Essex Windsor Loop 

When: Saturday, September 1 to Monday, September 3 - 2018


Total Distance: 186km 

The Ride: Cycling in Canada's southernmost region, Essex County, offers spectacular scenery including wineries and waterways, as well as picturesque riding along the shores of the Detroit River in Windsor. Make the most of a long weekend, cycling this curated, two night, three day, long weekend tour. Starting and ending in Comber, this route takes in beautiful riding, following the Great Lakes Waterfront Trail west along the southern shore of Lake St. Clair and riverfront in Windsor. Plan to slow down the pace to take in the scenery and waterfront rest stops and villages. Enjoy a night in Windsor before pedalling through EPIC Wine Country and on to Leamington for the second night. For the last day of riding, explore the natural beauty and beaches of Point Pelee National Park before riding back to Comber. This small group tour includes 2 nights' hotel accommodations, 2 breakfasts and 3 lunches, snacks, juices and water, parking, Point Pelee National Park admission and a support van transporting luggage. We make it easy - Just bring your bike and ride.

Experience Level and Ride Guide: Moderate. Riders on this ride need to have some experience riding on roads with vehicle traffic as the route is a mix of paved roads and trails or park roads. Not all roads have bike lanes or paved shoulders to ride on. Some of the road route is on very quiet country roads, other segments are busier. Off-road trails incorporate a mix of paved and unpaved surfaces, however unpaved segments are hard packed and easy to ride. This route has limited elevation changes and the flat terrain makes this ride suitable for hybrid bikes, mountain bikes or road bikes with wider tires. Enjoy a group ride option or ride at your own pace using detailed maps and information provided.  

View Route: Ride with GPS

What's Included: Overnight accommodation in Windsor and in Leamington at the certified bicycle friendly Quality Inn, 3 lunches, 2 breakfasts, parking, van support, luggage transfer, Point Pelee National Park admission, group ride option, detailed maps, evening social, snack and water stops.

Tour Price: $349 + HST (per person based on double occupancy). Single supplement pricing as well discounted rate for triples, quads and youth (16 & Under) available upon request.

Booking Details: Call Katharine Morewood, Licenced Travel Agent at OK Cycle & Adventure Tours, toll-free 1-888-621-6818 or email [email protected].

Read our Terms & Conditions for more information
Book Now Button

Bookings Administered by OK Cycle & Adventure Tours
 TICO Ontario Registration No: 50022848  
top10cycling  Windsor Eats  Windsor Eats2

Day 1:
Saturday, September 1 – Comber to Windsor - 52km

Starting in Comber, load up on supplies before meeting with the group at the designated parking lot for check-in and ride briefing. A short ride north through agricultural lands brings riders to Lake St. Clair. Head west on rural roads, following the signed Great Lakes Waterfront Trail, with the lake never far off. Stop at beaches or lakeside communities to explore more. Continue riding west along a mix of quiet suburban roads and city trails into the city of Windsor. Spend time exploring the riverfront park and downtown. With a burgeoning culinary scene, a visit to any of the city's popular restaurants and cafes is a must. If a drink is what you're after, this city is embracing it's prohibition past and features a number of local craft distilleries and breweries. Later that evening, catch up with other riders at a group social. Overnight and enjoy a warm welcome at the trailside accommodation. 

Start Time: Tour departs at 10:00 am from Comber, west of Chatham. Exact location to be announced.

Day 2:
Sunday, September 2 – Windsor to Leamington - 73km

Connecting back on to the Great Lakes Waterfront Trail, ride west along the paved path and the shore of the Detroit River with views across to `Motor City`. Leaving town, ride along quiet city streets and park paths to the spectacular Herb Gray Parkway, a paved multi-use trail with community art installations along the way. A short ride east connects riders to the well-maintained Chrysler Canada Greenway, a 42km rail trail that travels south through quiet rural landscapes and into the heart of one of Ontario`s popular wine regions. Stop for a refreshment break in Harrow or at any one of the many wineries that are a short jaunt off the main trail. The trail stretches east past farms and through the town of Kingsville with its boutique shops and restaurants, heading towards the day's end destination, Leamington. Cruise the final few kilometres into Leamington along quieter roadways arriving at the certified bicycle friendly, Quality Inn. Settle into your accommodations, explore Leamington or head south to beautiful waterfront promenade to catch a sunset or perhaps watch a ferry arrive in the harbour. 


Day 3:
Monday, September 3 – Leamington to Comber - 61km

The final day of riding offers both a mix of quiet roads and off-road trails. Beginning the ride out from Leamington, head south along a peninsula with frequent views of Lake Erie. Enjoy a pedal to the sunny and sandy shores of Lake Erie as you enter Point Pelee National Park (park admission is covered in cost of tour). Ride out along a crushed stone park path, connecting further south along a quiet park road to the southern tip of Canada`s mainland for a cool off or just take in the view. Ride back to Leamington for lunch overlooking the water. The park is a part of an important bird and butterfly migration corridor, and with a stroll out onto the floating marsh boardwalk, timing may be right to witness the fall Monark butterfly migration. The final stretch of the ride, through bountiful agricultural lands of Essex County at the beginning of harvest season, takes cyclists north following the Trans Canada Trail for an easy afternoon of off-road trail riding and return to start location in Comber.    

End Time: Approximately 4:30pm or at your own pace, at Comber. 


Additional Visitor Information:

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

Getting To/From Start:
Comber is conveniently located just south of the County Road 77 exit (#77) on Hwy 401. 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

    Waterfront  Riverwalk Trail Windsor Goh Iromoto  

Photo Credits: Tourism Windsor Essex Pelee Island, Windsor Eats, Destination Ontario

Booking Details: Call Katharine Morewood, Licenced Travel Agent at OK Cycle & Adventure Tours, toll-free 1-888-621-6818 or email [email protected].

Read our Terms & Conditions for more information
Book Now Button

Bookings Administered by OK Cycle & Adventure Tours
 TICO Ontario Registration No: 50022848  

For More Information Contact:

Ontario By Bike
Phone: 416-827-2772 / 1-866-701-2774
Email: info (at) ontariobybike.ca

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