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2018 Small Group Tours

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We've wrapped up our small group tours for 2018, having ridden over 500km with over 125 cyclists to 4 amazing destinations across Ontario! Sign up to our newsletter to recieve notice of our 2019 schedule or visit our Ontario By Bike Ride page to download these self-guided itineraries and ride them on your own!

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2018 Cycling In Ontario Guide

Cycle Tourism Conference 2019

Cycle Tourism Conference 2019 Toronto Canada

Ontario By Bike and Transportation Options are proud to announce the 2019 Cycle Tourism Conference, a full-day conference to be held in downtown Toronto on March 1, 2019. Call for Proposals and Sponsorships now open. Registration opens soon!

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Great Late Season Rides in Haldimand County

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Pair Haldimand's signed 69km River Route with cooler weather and a clear crisp autumn day with lovely countryside riding along the Grand River, Lake Erie waterfront and the charming small towns of Cayuga and Dunnville. Think great riding, smooth coffee and giant mudcats!  

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Celebrate by Bike

Ontario150 flash final1Choose to explore Ontario on one of these 15 world class, legacy cycling itineraries! Read More...

Ride These Epic Routes

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Explore 3,000km+ of extraordinary cycling
along the Great Lakes Waterfront Trail and Greenbelt Route.

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Ontario By Bike Blog

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Read on for inspirational cycling experiences across Ontario. Whether you're looking for rail trails, mountain biking or road riding, we're putting together stories to get you out on two wheels. Join us on Facebook, Twitter and Instagram to get more updates and so we can hear your story. Interested in guest blogging with Ontario By Bike? Shoot us an email!


3 minutes reading time (507 words)

Cycling Adventures Await in Canada’s Deep South

Cycling in Essex County Ontario
Pedal your way through Canada`s southernmost peninsula, which provides a largely flat topography for recreational cyclists, families, or avid enthusiasts. The trails in the region connect to further excursions in EPIC Wine Country, Point Pelee National Park, on Pelee Island, along Windsor’s stunning riverfront, and are also part of the Trans Canada Trail and the Great Lakes Waterfront Trail.

Starting at the Ambassador Bridge, cruise the Windsor Riverfront for 8km of stunning Detroit skyline views. Along the way, check out the Windsor Sculpture Park and Dieppe Gardens. Cycle along the 17km Herb Gray Parkway Trail to lush Carolinian forest trails and the 22km Cypher Systems Trail. Hop on the ferry to Pelee Island and explore 34km of quiet country road routes, providing easy access to beaches, forests, and dunes.

Find more detailed information on cycling in the City of Windsor or for the County of Essex.

Looking for a ride-ready route?

There are many within the Windsor Essex region that suit all types of abilities and experiences!

Windsor Kingsville Essex Tour – A three-day,Windsor Kingsville Essex Tour Itinerary 130km journey is suitable for experienced touring cyclists. This route begins and ends in Windsor and takes riders along scenic rural roads to the heart of Canada’s southernmost wine region. Follow glistening Lake Erie and Detroit River shorelines and enjoy 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.

Underground Railroad Bicycle Route (Detroit Alternate) – Experienced and touring cyclists can follow the route that escaped slaves used to travel to Owen Sound from the southern United States. Access cycling route maps and explore; painting a picture of what the journey was like in the 1800s. Alternate routes through Detroit and Essex County were recently added to this 3200km route, part of the Adventure Cycling Route Network.

Great Lakes Waterfront Trail (Various Surfaces) – Ride any portion (approx. 412km) of this trail in Windsor Essex that stretches over 2,100km along Canada’s iconic Great Lakes coasts. The Great Lakes Waterfront Trail connects communities, First Nations, and 748 of Ontario’s finest parks and natural areas. Depending on the length or section of the trail, this route is suitable for both recreational and experienced cyclists. Following Lake Ontario’s shoreline from Quebec to Niagara-on-the-Lake, and Lake Erie from Fort Erie through Essex South, Windsor and Essex North; to be extended in 2018 past Grand Bend to the town of Collingwood on Georgian Bay. This well-mapped and fully signed route offers a mixture of paved on- and off-road trails. The route also includes a 28km circle route around Pelee Island.

Windsor Riverfront Trail (Paved Trail) - Suitable for families, as well as recreational and experienced cyclists, start off beginning at the foot of the Ambassador Bridge for 8km of a smoothly paved trail that winds its way along the Detroit River and passing Windsor Sculpture Park, and parks such as Dieppe Gardens in the heart of downtown Windsor.

BIKE.TRAIN.WINDSOR Credit Goh IromotoCredit: Goh Iromoto / Waterfront Regeneration Trust

Chrysler Canada Greenway (Stonedust) – Running south from Oldcastle (outskirts of Windsor), through towns of McGregor and Harrow, proceeding eastward to Ruthven (between Kingsville and Leamington), this 48km rail trail is ideal for families and recreational cyclists. The trail passes through agricultural lands, by historical buildings and award-winning wineries; connecting 25 natural areas and three watersheds. This southern-most section of the Trans Canada Trail is currently the backbone of the trail network through Essex County.

Cycling in Essex countyCredit: Tourism Windsor Essex Pelee Island

Point Pelee National Park
 (Various Surfaces) - Riding in Point Pelee National Park includes options totalling 19km, including 7.5km of crushed stone on the Centennial trail, which parallels the main road through the park from the park entrance to the Visitor Centre. Cyclists can also ride the seasonal 2.5km crushed stone biking trail between the Visitor Centre and the DeLaurier area creating a short loop (Note: this trail is closed to cyclists between April 15 and May 31 for birding). Those comfortable riding on roads can cycle 7km from the gate to the Visitor Centre on an asphalt, roadway  shared with vehicles. Finally enjoy a 2km roadway extension to the tip area (southernmost mainland Canada), closed to vehicular traffic during business hours.  

Windsor Arts Bike Route (Road and Paved Trail) – This self-guided tour is a perfect way for recreational cyclists comfortable riding on roads to explore the city of Windsor. Starting near the Ambassador Bridge, the route then heads south through city streets and features Windsor's many unique sculptures, historic murals, awesome street art and eclectic galleries.


Experiences that compliment the great cycling!

As a peninsula, Windsor Essex provides shoreline excursions which showcase various cultural attractions and accommodations along the way. The cultural backdrop and terroir welcome cyclists and connect them between various points of interest within districts and communities of the region.

Award-winning tour operator, WindsorEats, offers a Wine Trail Ride through the picturesque Lake Erie North Shore wine region while also providing Friday Night Lights, an urban experience in Windsor along the historic Detroit River. Sign up for their Bikes & Beer Cycling Tour, where you can explore the city one beer at a time. Cycle through the streets of Windsor, Ontario, sampling beers at local breweries and pubs (always drink responsibly). Farm Dog Cycles also provides excursions through EPIC (Essex Pelee Island Coast) Wine Country, featuring half and full day guided tours as well as self-guided tour options. On Pelee Island, Canada’s southernmost location, the eco-tourism company, Explore Pelee features bike tours while Comfortech Bikes, the island's only bicycle shop, provides bike rentals.

Being on an international border, the Two-Nation Destination experience connects Windsor Essex to “America’s Comeback City” and one of the fastest growing cities for cycling in North America, Detroit, and their trail system, which links to Michigan’s Iron Belle Trail. Notable events within the area include the family friendly and popular Essex Region Conservation Bike Tour, the Tour de Troit “Bike the Bridge”, where cyclists can cross the international border via the Ambassador Bridge, connecting Detroit, MI with Windsor, ON. The Tweed Ride allows cyclists to dress up in their finest vintage attire and cycle through Windsor heritage districts such as Sandwich Town and Old Walkerville; SCAR (South Coast Adventure Race), is a multi-sport adventure race that takes place in several municipalities in the Windsor-Essex region; Tour di Via Italia is the oldest, historical, international street race in Ontario featuring amateur and professional cyclists racing through the streets of Windsor’s own “Little Italy.”

The Greenbelt Brewery Discovery Route offers thirsty cyclists multiple stops along the Barrels, Bottles & Brews Trail. There are a myriad of accommodations to choose from which are cycle-friendly. For all certified bicycle friendly businesses in Windsor Essex and Pelee Island, click here.

For more information on cycle-friendly businesses and routes, go to www.visitwindsoressex.com/categories/cycling

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