Ontario By Bike – Self-Guided Cycling Itineraries and Ride Guides

Cataraqui Kingston Wolfe Cruiser – 160km – 3 days, 2 nights

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.
See below for 2 days / 1 night itinerary.

Full ride details HERE

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Stratford & Country Gravel Explorer – 132km – 2 days, 1 night

Enjoy this ride exploring Stratford and Perth County in Southwestern Ontario, using a mix of quiet gravel farm roads, trails and city streets. 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.

Full ride details HERE

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Caledon Trails & Backroads Explorer – 122km – 2 days, 1 night

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 the night. On this ride weekend pedal on a mix of forested trails, stunning paved and gravel roads, passing horse farms, forests, historic villages, and unique geographic sites like the Cheltenham Badlands. See another side of Ontario just outside the big city.

Full ride details HERE

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Sarnia Lambton Loop – 162km – 2 days, 1 night

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 fascinating 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. Learn about the rich local heritage in Dresden at the Josiah Henson museum and the history of the Underground Railway.

Full ride details HERE (2025 itinerary) & HERE (2021 itinerary)

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Lanark Trail Tour – 160km or 186km – 3 days, 2 nights

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.

Full ride details HERE (2025 itinerary) & HERE (2022 itinerary)

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Niagara Falls & Circle Route North – 108km – 2 days, 1 night

See the top sights and highlights of Niagara on this two-day loop following a part of the Niagara Circle Route and stay 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.

Full ride details HERE (2025 itinerary)

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Huron Coast Explorer – 177km – 3 days, 2 night

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, Point Clark, Paisley and Ripley. Explore endless sandy beaches, historic lighthouses, and vibrant towns filled with local shops, cafes and restaurants. This ride is great for cyclists who love varied riding terrain and scenery – including smooth paved waterfront trails, rail trails, and cottage and country roads. This ride is based out of Port Elgin for two nights, and includes a half-day, Day 1 ride based from Kincardine.

Full ride details HERE (2024 itinerary)

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Railway City & Erie Ports Tour – 122km – 2 days, 1 night

 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.

Full ride details HERE (2024 itinerary)

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Trent Severn Trail Tour – 119km – 2 days, 1 night

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 Trans Canada Trail (including the Lang Hastings & Kawartha rail trails) and the Victoria Rail Trail along a route that intersects five of the historic Trent Severn Waterway lock systems, includes six 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 (2024 itinerary) & HERE (2019 itinerary)

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1000 Islands St. Lawrence River Ride – 158km – 3 days, 2 nights

Cycle one of the most spectacular routes in Ontario discovering the 1000 Islands and St Lawrence River on a three day tour. Starting from Gananoque and ending in Cornwall, following the Waterfront Trail east, this ride is on a mix of trails and roads and includes the stunning 1000 Islands Parkway Trail and Long Sault Parkway. 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.

End to End Ride: This ride follows a linear route. Starting from Gananoque and ending in Cornwall.

Full ride details HERE (2024 itinerary) & HERE (2019 itinerary)
(Also see below for Out and Back and Looped Rides)

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Georgian Bay Collingwood Explorer – 80km or 120km – 2 days, 1 night

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.

Full ride details HERE (2023 itinerary)

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North Bay & Lakes Tour – 158km – 3 days, 2 nights

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 Callander and ride the city trails making delightful discoveries in and around North Bay.

Full ride details HERE (2023 itinerary)

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Oxford Rural Road Ride – 173km – 2 days, 1 overnight

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. 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 to, by the seat of a bike! This route is almost entirely on paved roads. Roads selected are designated bike routes, primarily on quiet rural roadways with limited paved shoulders.

Full ride details HERE (2023 itinerary) & HERE (2019 itinerary)

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Toronto Trails & Ravines Ride– 85km – 2 days, 1 night – OR – daytrip

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. Stop downtown at Harbourfront, explore the Leslie Street Spit, and enjoy the fine white sands of Woodbine Beach. Set a relatively leisurely pace and peel off to enjoy some of the many natural and cultural sights or city attractions along the way.

Full ride details HERE (2023 itinerary) & HERE (2018 itinerary)

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Hamilton Brantford Paris Port Dover Trail Ride – 110km or 137km – 2 days, 1 overnight

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.

Full ride details HERE (2022 itinerary) & HERE (2015 itinerary)

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Uxbridge Kawarthas Rail Trail – 85km or 100km – 2 days, 1 night

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.

Full ride details HERE (2022 itinerary) & HERE (2018 itinerary)

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Essex Windsor Loop – 193km – 3 days, 2 nights

Enjoy an overnight cycling trip in Canada’s southernmost region, Essex County, which offers spectacular cycling and scenery including wineries and waterways, as well as picturesque riding along the shores of Lake St. Clair, Detroit River and Lake Erie. Starting and ending in Comber, this route follows portions of the Great Lakes Waterfront Trail along the southern shore of Lake St. Clair and riverfront in Windsor. Enjoy a night in Windsor before pedalling through EPIC Wine Country and on to Leamington for the second night. The last day of riding explores the natural beauty and beaches of Point Pelee National Park.

Full ride details HERE (2022 itinerary) & HERE (2018 itinerary)

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Cataraqui Kingston Cruiser – 116km – 2 days, 1 night

Enjoy Ontario By Bike’s new tour route 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 (2021 itinerary)

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Waterloo Guelph Explorer –  115km – 2 days, 1 night

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. The route is approximately half road and half trail. Some segments of off-road trails are unpaved but hard-packed, and easy to ride. A portion of the ride will be on roads, some smaller rural roads without bike lanes or paved shoulders, as well as some connector stretches on busier roads with more traffic.

Full ride details HERE (2020 itinerary)

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Ottawa City & Country – 92km – 2 days, 1 night

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 a two-day getaway. Day 1 route is on quiet country roads, with no bike lanes or paved shoulders. Day 2 features off-road trails that are all on paved surfaces.

Full ride details HERE (2019 itinerary)

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1000 Islands St. Lawrence River Ride – 147km to 179km – 3 days, 2 nights
Out and Back and Looped Rides

Cycle one of the most spectacular routes in Ontario discovering the 1000 Islands and St Lawrence River on a three day tour. This ride is on a mix of trails and roads with beautiful riverfront riding, interesting historic and quaint communities along the way. Starting from and using both Brockville and Morrisburg as your base, enjoy 3 days of cycling following the Waterfront Trail east and west, riding out and back daily or following a looped route that incorporates trail and country roads.

Full ride details HERE (2021 itinerary) & HERE (2020 itinerary) 

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Georgian Bay Explorer – 95km – 2 days, 1 night

Ride along the picturesque southern shores of Georgian Bay in Grey County, featuring an even mix of well-kept rail trails and quiet rural roads, both paved and unpaved. Explore the northern reaches of the Niagara Escarpment with frequent stunning views of the region with vistas across the glistening waters of Georgian Bay.

Full ride details HERE (2017 itinerary)

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Simcoe County Rail Trails  – 2 days, 1 night

Ride the rail trails and connected paths that loop around Simcoe County from the outskirts of Barrie, to Elmvale, Balm

Beach, Penetanguishene, Midland, Waubaushene, Coldwater and Orillia. Stop in towns and at historic sites, enjoying the picturesque shores of Severn Sound, Georgian Bay and pleasant countryside.

Snow Valley Ski Resort Starting Point (108km to 145km): Starting from the Snow Valley Ski Resort with a possible extension into Barrie. The route quickly connects to the primarily crushed gravel North Simcoe Rail Trail heading northwest towards Georgian Bay.

Full ride details HERE (2016 itinerary)

Barrie, Georgian College Starting Point (164km): Starting from downtown Barrie, follow a 16km road route connecting to the North Simcoe Rail Trail travelling through the Minesing Wetlands, one of Ontario’s largest remaining wetlands, before connecting along the not-so-short 23km Tiny Trail just north of Elmvale.

Full ride details HERE (2020 itinerary)

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Niagara Circle Route South – 127km – 2 days, 1 night

Explore the quieter side of Niagara, on this 2 day ride, primarily on well paved off-road trails that make an easy flat loop passing through Thorold, Niagara Falls, Fort Erie, Port Colborne, and Welland. Discover rivers, canals and welcoming communities along the way.

Full ride details HERE (2021 itinerary) & HERE (2018 itinerary)