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Ontario By Bike Rides 2026

Explore more of Ontario by bike!

Booking and full itinerary details for our 2026 Rides are now available!

Ontario By Bike Rides are weekend long, small group, self-guided and supported rides with hotel accommodations, meals and more included. Enjoy a group ride option or ride at your own pace using detailed maps and information provided. Click the links below for full details on each ride, route maps, daily ride itineraries, inclusions, accommodations, prices and how to book.

We make it easy – Just bring your bike and ride!

2026 Ontario By Bike Ride Destinations

Stratford & Country Gravel Explorer

Stratford & Perth County, Ontario

Dates: May 23-24, 2026 (2 days / 1 night)
Total Distance: 156km

Join us for an early season gravel grinder and put some kilometres on your bike exploring Stratford and Perth County in Southwestern Ontario. Known for its theatre crowd and annual Festival, stay in Stratford, a lively and small city on the beautiful Avon River. Pedal through nearby countryside and farmlands to the picturesque town of St. Marys in the south and to the G2G Rail Trail, with Milverton and Millbank as stops to the north, on this weekend long, two-day ride adventure.

This Ride is now over. Find detailed itinerary for a self-supported experience HERE.

Cataraqui Kingston Wolfe Cruiser

Dates: June 13-15, 2026 (3 days / 2 nights)
Total Distance: 160km

Enjoy this tour in Southeastern Ontario, riding some of the top rail trails in the region, taking in waterfront vistas, quiet island road riding and stops in pretty small and large communities along the way. Ride the well-groomed Cataraqui and K&P rail trails following creeks, past marshes and lush agricultural lands into Kingston. Enjoy two nights staying in downtown Kingston, close to all the action, cafes, shops and the city’s scenic lakeside trail. On day two, take the ferry and explore the beautiful, quiet paved and gravel road cycling on Wolfe Island, with expansive Lake Ontario views, wind mills, and a beach stop. On the last day, ride west from Kingston stopping at historic sights along the Loyalist Parkway and Waterfront Trail. From the village of Bath, pedal inland through flat and picturesque farmlands on quiet country roads, returning to Napanee.

This Ride is now over. Find detailed itinerary for a self-supported experience HERE.

Simcoe-County-Loop

Simcoe County Loop Trail (Sold out, waitlist only)

Dates: August 29-31, 2026 (3 days / 2 nights)
Total Distance: 173km

Discover the fantastic connected rail trails in Simcoe County on a leisurely three-day loop ride and a perfect itinerary for recreational riders to explore the area and see all there is to see trailside as well as in the towns and hamlets enroute. Featuring the well-maintained Uhthoff, Tay Shore and Tiny Trails, this ride will bring you alongside the rugged waterfront of Severn Sound in southern Georgian Bay, as well as to Lake Simcoe and Lake Couchiching. From the water, follow the trails through beautiful forests and countryside in the heart of Simcoe County, and enjoy hotels overnight in Orillia and Midland.

This Ride is now SOLD OUT. Find waitlist info and ride details HERE

Guelph Wellington Routes & Rivers 

Dates: September 26-27, 2026 (2 days, 1 night)
Total Distance: 141km

Enjoy a fall cycling weekend exploring the picturesque country roads and trails, historic towns, and stunning waterways of Wellington County, based from the city of Guelph, a vibrant and modern university town. Pedal rural roads to Elora and Fergus, taking in the historic limestone buildings and artisanal shops and cafes perched above the Grand River. Cruise the Elora Cataract Trailway and Guelph’s riverside trail system, enjoying visits to the region’s diverse conservations areas. Don’t miss this two-day ride weekend with an incredible blend of rural scenery, nature and culturally rich communities.

Limited Space Available – Ride Details and Booking HERE

Ontario By Bike Rides

Past Trip Itineraries

Enjoy one of our past trip itineraries, available online so you can enjoy on your own self-guided ride experience.

See map and page with all past itineraries at: www.ontariobybike.ca/itineraries

Niagara Falls & Circle Route North

Total Distance: 108km

See the top sights in and highlights of Niagara on this two-day loop following a part of the Niagara Circle Route and staying the night in Niagara Falls. Visit the pretty communities of Port Dalhousie and Niagara-on-the-Lake. Meander alongside the Niagara River trail to the breathtaking and majestic Falls. Enjoy Niagara countryside along the way, farms, vineyards and waterways, the H2O Highway and the Welland Canal trail.

Ride Details and Self-Guided Itinerary HERE

Lanark Trail Tour

Total Distance: 160 or 186km

Discover the trails in Lanark County riding out and returning to Carleton Place, a pretty historic mill town and trail hub that make it a perfect base for three days of fantastic rides and touring in eastern Ontario. Learn more about the heritage waterways in the area with stops alongside the Rideau Canal and the Mississippi River, on rail trails that wind their way over quiet country side, criss-crossing rivers and passing through picturesque small towns and hamlets. Ride entirely on rail trails or branch out onto quiet roads for looped adventures to experience the best of scenic Lanark County, not far west of the nation’s capital, Ottawa.

Ride Details and Self-Guided Itinerary HERE

Sarnia Lambton Loop

Total Distance: 162km

Head to Sarnia Lambton to explore Ontario’s Blue Coast on a 162km looped ride adventure. Enjoy plenty of scenic waterfront riding along the St. Clair River and shores of Lake Huron as well as long stretches of quiet hinterland cruising through southern Ontario’s flat farmlands. Slow down to explore the rich local heritage in Dresden at Uncle Tom’s Cabin and the terminus of the Underground Railway, to the historic towns of Petrolia and Oil Springs, riding by the still active rigs and the world’s first commercial oil wells. Discover Sarnia, a waterfront city perched on the narrows where Lake Huron begins its flow south to Lake Erie, with Michigan a close river crossing away.

Ride Details and Self-Guided Itinerary HERE

Caledon Trails & Backroads Explorer

Total Distance: 122km

Discover the charming small towns, trails, and backroads of Caledon, a rural region set against the striking topography of the Niagara Escarpment, just outside of Toronto. This ride starts out from Brampton on the Etobicoke Creek Trail, leading to Caledon’s pastoral roads and signature rail trail enroute to Georgetown for an overnight. On this ride weekend, pedal on a mix of forested trails ablaze in fall colours, stunning paved and gravel roads, passing horse farms, historic villages, and unique geographic sites like the Cheltenham Badlands. See another side of Ontario just outside the big city.

Ride Details and Self-Guided Itinerary HERE

1000 Islands St. Lawrence River Ride

Ride Distance: 157km

Cycle one of the most spectacular routes in Ontario discovering the 1000 Islands and St Lawrence River on this three day, long weekend tour. Starting from Gananoque and ending in Cornwall, following the Great Lakes Waterfront Trail east, this ride is on a mix of trails and roads. Plan to slow down the pace to take in the scenery and make the most of waterfront rest stops and villages. Enjoy a night in Brockville before pedalling on to Morrisburg for the second night, and the last day of riding taking in an array of natural and heritage attractions in what was once called Upper Canada.

Ride Details and Self-Guided Itinerary HERE

Trent Severn Trail Tour

Ride Distance: 118km

This two-day tour is nearly all on rail trails with only limited residential street riding in Campbellford, Peterborough and Lindsay. Explore the rolling hills of Northumberland County (along a flat rail trail) and the rural expanse of the southern Kawarthas along with an overnight in the city of Peterborough. Enjoy superb cycling on the Trans Canada Trail (including the Lang-Hastings & Kawartha rail rails) and the Victoria Rail Trail along a route that intersects 5 of the historic Trent Severn Waterway lock systems, includes 6 major river crossings and the scenic views atop Ranney Gorge Suspension Bridge in Campbellford and Doube’s Trestle Bridge just outside of Omemee.

Ride Details and Self-Guided Itinerary HERE

Railway City & Erie Ports Tour

Ride Distance: 121km

Discover the charm and unique character of south western Ontario on this ride through Elgin County. Venturing out from St. Thomas, once an important railway hub and a celebrated heritage, explore the area along quiet farm roads through lush forests and picturesque countryside. Pedal scenic coastal routes and the Great Lakes Waterfront Trail to vibrant villages on the Lake Erie shoreline. Stop at the renowned beaches of Port Stanley and Port Bruce on this weekend full of fun and adventure.

Ride Details and Self-Guided Itinerary HERE

Huron Coast Explorer 

Ride Distance: 177km

Discover Ontario’s stunning Lake Huron coast and the beautiful communities that make up the town of Saugeen Shores – Port Elgin, Southampton, plus the neighbouring communities of Sauble Beach, Kincardine, Paisley and Ripley. Explore endless sandy beaches, historic lighthouses, and vibrant towns filled with local shops, cafes and restaurants. This ride will be great for cyclists who love varied riding terrain and scenery – including smooth paved waterfront trails, rail trails, cottage and country roads, and a gravel ride option through rolling countryside. This ride will be based out of Port Elgin for two nights, and includes a half-day, Day 1 ride based from Kincardine.

Ride Details and Self-Guided Itinerary HERE

Oxford Rural Road Ride

Ride Distance: 159km

Oxford County, located in southwest Ontario, isn’t just the Dairy Capital of Canada, the county is also one of the best destinations in Ontario for road cycling. Experience it for yourself, on a two day road tour and loop around Oxford County. Flat, quiet and well-paved roads will take cyclists past rural landscapes and working farms, which are broken up only by quaint and distinct small towns and villages. Home to the Cheese Trail, this tour will showcase the unique heritage and natural attractions of Oxford County the best way we know how, by the seat of a bike!

Ride Details and Self-Guided Itinerary HERE

Toronto Trails & Ravines Ride

Ride Distance: 85km+

Discover another side to the big city on this looped tour around Toronto. Ride on a mix of park, ravine, hydro corridor and waterfront trails on this 85km+ route. Learn more about and experience the city’s heritage waterways and unique ravines system, pedalling the Humber and Don Valley Trails. Set a relatively leisurely pace and peel off to enjoy the many natural and cultural sights or city attractions along the way. Stop downtown at Harbourfront, explore the Leslie Street Spit and enjoy downtown accommodations just steps from the Distillery District.

Ride Details and Self-Guided Itinerary HERE

North Bay & Lakes Tour 

Ride Distance: 157km+

Discover the near north with three days of riding adventures touring lakes, bays and heritage waterways. Follow the Voyageur Cycling Route and experience the ‘Spirit of the Bay’ around Ontario’s fourth largest lake, Lake Nipissing. Visit small towns and villages from South River to Callandar and ride the city trails making delightful discoveries in and around North Bay.

Ride Details and Self-Guided Itinerary HERE

Georgian Bay Collingwood Explorer 

Ride Distance: 80km or 118km

From Collingwood and the Blue Mountains, explore the natural beauty of southern Georgian Bay and discover why this area is so popular with cyclists and all season outdoor adventurers. Never far from the blue water views of the Bay, the jagged cliffs and greenery of the Niagara Escarpment, sample the local flavours, visit heritage town centres and artisans galleries, on peaceful off road trails and looped routes that include country road returns on this weekend long ride.

Ride Details and Self-Guided Itinerary HERE

Essex Windsor Loop

Total Distance: 188km

Make the most of a long weekend, cycling waterways and past wineries on this three day tour in Canada’s southernmost region. Enjoy a beautiful and scenic ride 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 pedaling through EPIC Wine Country and on to Leamington, exploring the natural beauty and beaches of Point Pelee National Park before looping back to the start in Comber.

Ride Details and Self-Guided Itinerary HERE

Uxbridge Kawarthas Rail Trail

Total Distance: 85km or 100km

Enjoy this weekend-long, quiet and safe off-road rail trail ride from Uxbridge through the Kawarthas ending at your choice destination of Peterborough or Lakefield, with a bus shuttle provided back to ride start location on Sunday. Whether you ride independently or with friends, make the most of this linear trail. The well-maintained, hard-packed trail, with some paved sections, traverses idyllic farmlands, runs alongside waterways and canals, and through lush green forests. With plenty of stop options on bridges and in parkland, the ride between small towns and bigger city attractions plus a half-way overnight stay in Lindsay will make it seem a world away from your day-to-day.

Ride Details and Self-Guided Itinerary HERE

Lanark Trail Tour 

Total Distance: 160km or 186km

Discover the trails in Lanark County riding out and returning to Carleton Place, a pretty historic mill town and trail hub that make it a perfect base for three days of fantastic rides and touring in eastern Ontario. Learn more about the heritage waterways in the area with stops alongside the Rideau Canal and the Mississippi River, on rail trails that wind their way over quiet country side, criss-crossing rivers and passing through picturesque small towns and hamlets. Ride entirely on rail trails or branch out onto quiet roads for looped adventures to experience the best of scenic Lanark County, not far west of the nation’s capital, Ottawa.

Ride Details and Self-Guided Itinerary HERE

Hamilton Brantford Paris Port Dover Trail Ride 

Total Distance: 92km or 124km

Experience the spectacular off-road rail trail ride from Hamilton to Paris, Brantford to Port Dover, with ride ending on the shores of Lake Erie. Shorter or longer route options are available so you can make the most of the ride and time out on this interconnected well maintained trail system. Passing through many communities along the way, take time out to enjoy the sights, whether choosing to ride with friends, the group or independently. Enjoy a one-way linear route with bus shuttle provided at ride end in Port Dover to ride start in Dundas.

Ride Details and Self-Guided Itinerary HERE 

Niagara Circle Route South

Total Distance: 127km

The Ride: A two day weekend tour and primarily off-road ride along the Greater Niagara Circle Route. Discover the quieter side of Niagara and Niagara south, with this spectacular trail ride along the Niagara River Recreational Trail, the Friendship Trail and the Welland Canal Parkway Trail. Fully paved with only 24km of the 127km on roads, as well as flat easy riding conditions will make for a wonderful weekend getaway and cycling experience. Including a unique ferry jaunt over the Welland Canal, this looped route is well suited for all types of cyclists. The tour includes hotel accommodations, lunches, ride support and more. Just bring your bike and ride.

Full ride details HERE

Sarnia Lambton Loop

Total Distance: 161km

The Ride: Head to Sarnia Lambton to explore Ontario’s Blue Coast on a 161km looped ride sure to be a great weekend long cycling adventure. Enjoy plenty of scenic waterfront riding along the St. Clair River and shores of Lake Huron as well as long stretches of quiet hinterland cruising through southern Ontario’s flat farmlands. Slow down to explore the rich local heritage starting in Dresden at Uncle Tom’s Cabin and the terminus of the Underground Railway, to the historic towns of Petrolia and Oil Springs, riding by the still active rigs and the world’s first commercial oil wells. Spend the night in Sarnia, a waterfront city perched on the narrows where Lake Huron begins its flow south to Lake Erie, with Michigan a close river crossing away. The tour includes hotel accommodations, lunches, ride support and more. Just bring your bike and ride.

Full ride details HERE

1000 Island St. Lawrence River Ride

Total Distance: 147km

The Ride: Join Ontario By Bike on our popular long weekend bike tour! Cycle one of the most spectacular routes in Ontario discovering the 1000 Islands and St. Lawrence River on a three day, long weekend tour. Starting from Brockville and Morrisburg, this tour, following the Great Lakes Waterfront Trail east, features a mix of trails and roads. Plan to slow down the pace to take in the scenery and make the most of waterfront rest stops, villages and attractions. Enjoy a night in Brockville, and Morrisburg for the second night, with the final day of riding taking in an array of natural and heritage attractions in a region once more commonly known as ‘Upper Canada’.

Full ride details HERE

Cataraqui Kingston Cruiser

Total Distance: 121km

The Ride: Join Ontario By Bike on a brand new tour in south eastern Ontario to experience some of the top rail trails in the region, waterfront vistas and stops in pretty small and large communities along the way. Ride the well-groomed Cataraqui and K&P rail trails following creeks, past marshes and lush agricultural land into Kingston. Enjoy an overnight stay at a downtown waterfront hotel, close to all the action, cafes, shops and the city’s scenic lakeside trail. On day two enjoy the spectacular views following the shores of Lake Ontario and stopping at historic sights along the Loyalist Parkway. From the village of Bath enjoy riding inland through flat farmlands on quiet country roads, returning to Napanee.

Full ride details HERE

Waterloo Guelph Explorer

Total Distance: 115km

The Ride: Explore the Waterloo region and Guelph area on this two day 115km looped ride. Enjoy a mix of scenic rural and urban sights on a weekend ride that uses a variety of off-road trails for over half the total tour distance. Cycle through Mennonite country on quiet stretches of road, with time to stop in small communities along the way as well as the famed Kissing Bridge, in Montrose. Visit the vibrant downtown cores and explore Guelph and Waterloo by bike. View full details and download self-guided itinerary

Full ride details HERE

Ottawa City and Country

Total Distance: 92km

The Ride: Explore Ontario’s capital city and surrounding countryside, a top cycling destination in the province. With rural settings, just a short distance from the downtown core, ride quiet country back roads and enjoy the peaceful scenery along with the many attractions near the village of Carp. Add a ride along the pathways and trail system in the urban centre following both canals and rivers and get to experience the best of biking in Ottawa over this two-day cycling adventure.

Full ride details HERE

Oxford Rural Road Ride

Total Distance: 173km

The Ride: Oxford County, located in southwest Ontario, isn’t just the Dairy Capital of Canada, the county is also gaining a reputation as one of the best destinations in Ontario for road cycling. Experience it for yourself on this two-day recreational road tour and loop around Oxford County. Flat, quiet and well-paved roads will take cyclists past rural landscapes and working farms, which are broken up only by quaint and distinct small towns and villages. Home to the Cheese Trail, this tour will showcase the unique heritage and natural attractions of Oxford County the best way we know how, by the seat of a bike!

Full ride details HERE

Total Distance: 97km or 119

The Ride: A new spin on an Ontario By Bike classic, this two-day tour is nearly all on rail trails with only limited residential street riding in Campbellford, Peterborough and Lindsay. Explore the rolling hills of Northumberland County (along a flat rail trail) and the rural expanse of the southern Kawarthas along with an overnight in the city of Peterborough. Enjoy superb cycling on The Great Trail (including the Lang Hastings & Kawartha rail trails) and the Victoria Rail Trail along a route that intersects 5 of the historic Trent Severn Waterway lock systems, includes 6 major river crossings and the scenic views atop Ranney Gorge Suspension Bridge in Campbellford and Doube Trestle Bridge just outside of Omemee.

Full ride details HERE

Toronto Trails & Ravines

Total Distance: 90km

The Ride: Discover another side to the big city on this weekend long looped tour around Toronto. Ride on a mix of park, ravine, hydro corridor and waterfront trails on this 2 day, 90km route. Learn more about and experience the city’s heritage waterways and unique ravines system, pedalling the Humber and Don Valley Trails. Stop downtown at Harbourfront, explore the Leslie Street Spit, and enjoy the fine white sands of Woodbine Beach. Setting a relatively leisurely pace, ride with group or peel off to enjoy some of the many natural and cultural sights or city attractions along the way. This ride was a part of the Adventure Cycling Association’s 3rd annual Bike Travel Weekend.

Full ride details HERE

Essex Windsor Loop

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.

Full ride details HERE

Simcoe County Rail Trail Weekend

Total Distance: 108km (145km with route extension to Barrie)

The Ride: Located just over an hour north of Toronto, Simcoe County has a rail trail network that loops and criss-crosses the region, making it a fabulous destination for recreational riders looking to explore the region by bike. Join us for a fabulous two day weekend tour along some of the best trails in Simcoe County. Passing through several small towns and by historic sites along the route, enjoy an easy ride on trails of mixed surfaces. Featuring rail trail riding along portions of the Trans Canada Trail, including the well-maintained Uhthoff and Tiny Trails, the route brings the group along the rugged shores of Severn Sound in Georgian Bay and through the beautiful countryside of Simcoe County. This itinerary suggests an overnight stay in Midland.

Full ride details HERE

Niagara Circle Route South

Total Distance: 118km

The Ride: A two day weekend tour and primarily off-road ride along the Greater Niagara Circle Route. Discover the quieter side of Niagara and Niagara south, with this spectacular trail ride along the Niagara River Recreational Trail, the Friendship Trail and the Welland Canal Parkway Trail. Fully paved and easy riding conditions, with all details outlined in the itinerary, will make for a wonderful weekend getaway and cycling experience. With limited road riding and unique ferry jaunt over the Canal, this looped ride is well suited for all types of cyclists.

View 2021 self-guided itinerary HERE (including construction updates.) 

View 2018 self-guided itinerary HERE.

Uxbridge Kawarthas Rail Trail Weekend

Total Distance: 85km to 100km

The Ride: Enjoy this weekend-long, quiet and safe off-road rail trail ride from Uxbridge through the Kawarthas ending at your choice destination of Peterborough or Lakefield. Whether you ride independently or with friends, this Ontario By Bike Ride itinerary features a linear trail, so arrangements will need to be made to either cycle back to the start or prepare vehicle pick-up in advance. The well-maintained hard packed trail, with some paved sections, traverses idyllic farmlands, along waterways and canals, and through lush green forests. Trailside hotels, bicycle friendly businesses, Doube’s Trestle Bridge, Peterborough Lift Lock and the Trent-Severn Waterway are all featured on this itinerary with a suggested overnight stop in Lindsay and lunch the following day in Peterborough. This popular route was part of the June 2015 and September 2017 rides.

Full ride details HERE

Hamilton Brantford Paris Port Dover Trail Weekend

Total Distance: 92km to 117km

The Ride: Enjoy fabulous two-days or a weekend of riding on a spectacular off-road rail trail ride from Hamilton to Brantford, Paris to Port Dover, with ride ending on the shores of Lake Erie. Shorter or longer route options are available so you can make the most of the ride and time out on this interconnected well maintained trail system. Passing through many communities along the way, take time out to enjoy the sights, whether choosing to ride with friends or independently. This tour incorporates one overnight stop near Brantford, however this could be modified to include an overnight in Paris or elsewhere. Many bicycle friendly businesses are located throughout these regions, with many memorable ride highlights including the Hamilton-Brantford Rail Trail, the town of Paris on the Grand River, and the Black Bridge in Waterford.

Full ride details HERE

Georgian Bay Explorer

Total Distance: 95km

The Ride: Ride along the picturesque southern shores of Georgian Bay in Grey County. This suggested two-day weekend itinerary features an even mix of riding along well-kept rail trails and quiet rural roads, both paved and unpaved. Starting from Stayner in the east and ending in Owen Sound, the route brings cyclists up and around the northern reaches of the Escarpment with frequent opportunities to cool off in Georgian Bay. Enjoy picturesque riding in southern Georgian Bay, connecting to quaint towns and villages along the way. Enjoy an evening in Meaford before continuing the ride west along country roads with vistas across the glistening waters of Georgian Bay.

Full ride details HERE

1000 Island St. Lawrence River Ride

Total Distance: 158km

The Ride:Cycle one of the most spectacular routes in Ontario discovering the 1000 Islands and St Lawrence River on this suggested three day itinerary. Starting from Gananoque and ending in Cornwall, following the Great Lakes Waterfront Trail east, this ride is on a mix of trails and roads. Plan to slow down the pace to take in the scenery and make the most of waterfront rest stops and villages. Enjoy a night in Brockville before pedalling on to Morrisburg for the second night, and the last day of riding taking in an array of natural and heritage attractions in what was once called Upper Canada.

View 2021 and 2020 looped itineraries HERE. 

View full details & download self guided end to end itinerary HERE. 

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

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Published On: February 1, 2022Categories: Events & Tours, Home

About the Author: Ontario By Bike