Simcoe County

• Orillia Millenium Trail – This paved lakefront trail runs 10km through Orillia and is popular with all types of users.
• Lake Country Oro-Medonte Rail Trail – An abandoned CN rail line (stone dust), it runs 28km along the western flank of Lake Simcoe, from Barrie to Orillia.
• Ramara Rail Trail – East of Orillia, this 5km stone dust trail parallels Rama Road on the east side of Lake Couchiching, to the Mara-Rama boundary.
• Thornton-Cookstown Trail – This 16km stone dust trail is an old rail line south of Barrie. Also part of the TransCanada Trail, the trail runs through green pastures and forests, and crosses Cookstown Creek six times.
• Uhthoff Trail – Running northwest from Orillia through scenic woods and wetlands, this stone dust trail is part of the TransCanada Trail. The final section from Coldwater opened in 2013 and completes the 30km route to Waubaushene.
• Tay Shore Trail – These paved trails follow close to the waterfront for 16km from Waubaushene to Midland and connects onwards as part of the Simcoe County Loop Trail. In addition to passing through these communities, the trail passes Ste. Marie Among the Hurons (near Midland), a heritage attraction which recreates a settlement from 1600s.
• Penetanguishene Trails – Trails through town and roads, 5.5km from the Mid-Pen Link and onwards to the Tiny Trail. Cycle through downtown and harbour parks including Rotary Champlain Wendat Park. A part of the Simcoe County Loop Trail.
• Tiny Trail & North Simcoe Rail Trail – Combined, these two trails cover 55km, south from Penetanguishene, first on the Tiny Trail (23km), and continuing south from Elmvale to just west of Barrie on the North Simcoe Rail Trail (32km). The multi-use trail surface is primarily stone dust. The trail crosses 14 historic bridges and passes through Mayer’s Marsh and the Minesing Wetlands, which are internationally significant eco-systems and excellent birding spots.
• Awenda Provincial Park – Several kilometres of park roads are available for cyclists. Bikes are also allowed on the Beach, Bluff and Brule Trails, totalling 21km. Since these are multi-use trails, racing is not permitted and cyclists must yield to pedestrians and hikers. Cyclists are encouraged to respect and protect the often sensitive environments that these trails pass through by riding only on the designated trail surface. Trails are designed for hiking and are more suited to mountain bikes.
• Wasaga Beach Shore Lane Trail – A 19km mixed surface trail follows waterfront from Archer Road in the east, through Wasaga Beach Provincial Park to Fairgrounds Road, on the outskirts of Collingwood, in the west. The trail connects the many beaches and beach community along Nottawasaga Bay.
• Collingwood Waterfront Trail – The 5km mixed surface trail zig-zags along the Collingwood waterfront connecting with several road loops which run south from Collingwood, into Simcoe and neighbouring Grey County.
• Collingwood Loop Trail – This 6km trail takes cyclists and hikers on a loop through greenways, riverbeds and the waterfront in the town of Collingwood. Mixed surface with some portions paved, this easy trail is used for both cycling and hiking.
• Clearview Collingwood Train Trail – This 12km stone dust trail follows the abandoned rail line running southeast through the tranquil landscape from Collingwood to Stayner. New in 2025 trail is extended from Stayner to Angus, 23km in total from Collingwood.
• Georgian Trail – This classic and well maintained rail trail is an easy 32km ride on stone dust between Collingwood and Meaford, with 30 access points. Enjoy a swim at several beaches en-route, or grab some nourishment at the trail-side kiosks, cafes and pubs along the way. Many local bike routes and loops use portions of this trail.

Simcoe County Loop Trail

The Simcoe County Loop Trail is a 160km loop that travels through nine municipalities, reaches three major bodies of water, including Georgian Bay, Lake Simcoe and Lake Couchiching. And, is primarily on off-road, multi-use rail trails! The route is flat, scenic and available as a multi-day tour. Riding counter clockwise:

• Barrie to Orillia – 42km – Starting from the Barrie waterfront on Kempenfelt Bay (near the Allandale GO station), the loop runs 42km northeast to Orillia along Lake Simcoe (Lake Country Oro-Medonte Rail Trail and Orillia Millennium Trail).
• Orillia to Pentanguishene – 59km- Riding out of Orillia northwest through Coldwater to Waubaushene (Uhthoff Trail), the trail snakes another 29km along the waterfront (Tay Shore, Midland and Penetanguishene Rotary Trails).
• Pentanguishene to Barrie – 65km – From Severn Sound, the loop travels south along the not-so-short Tiny Trail (23km) to Elmvale and continues along the abandoned North Simcoe Railway (32km) past the Minesing Swamp, one of Ontario’s largest remaining wetlands, ending just 10km west of Barrie.

Ontario By Bike Self Guided Itineraries – Ontario By Bike has hosted several small group tours on two-day cycling trips on trails in Simcoe County. One route itinerary starts and ends near Barrie, but can be started any where along the loop, and follows the Simcoe County Trail Loop through Midland, for overnight stop, and on to Orillia before ending in Barrie. Another, the Georgian Bay Explorer, starts in Stayner, continuing to Collingwood, overnight in Meaford and ends in Owen Sound. The Georgian Bay-Collingwood Explorer Ride is based from Collingwood and explorers the area’s trails and scenic rural roads over two days. Ontario By Bike has made available all digital and pdf mapping, as well as a self-guided itineraries at the links below, to share with individuals and groups that may be interested in riding the same route.

• Georgian Bay-Collingwood Explorer 
• Simcoe County Rail Trail
• Georgian Bay Explorer