Simcoe County Loop Trail

Multiday Trip – 2 or 3 Days

Total Distance: 153km  

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. This fabulous two (or three) day tour along some of the best trails in Simcoe County, passes through several small towns and by historic sites along the route. The ride brings the group along the rugged shores of Severn Sound in Georgian Bay and through the beautiful countryside of Simcoe County.

Experience Level: Easy to Moderate: While distances may be longer for recreational cyclists, this is 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.

View digital route of tour –

Day 1: Grenfell Community Hall to Midland – 62km

Area services along this section of the route: Accommodations, cafés, restaurants, grocery stores, shopping, banking, bike shops (in Midland), attractions and trails.

Follow routing for 3km before connecting to the North Simcoe Rail Trail and heading north towards Georgian Bay for 27km. This route travels past the Minesing Wetlands, one of Ontario’s largest remaining wetlands, before connecting along the not-so-short Tiny Trail (23km) just north of Elmvale. If you’re not packing your lunch, consider stopping at Elmvale to grab something to go, or eat at one of the food services in town before continuing north. Travelling further north, there are several options for a beach detour towards Georgian Bay, including taking Balm Beach Road West for 3.5km to white sandy beaches. Others may choose to continue on to Penetanguishene, where the paved trail into town offers fun forested riding over 13 bridges. A partially paved, partially crushed gravel trail links into town and brings riders along the shores of the Severn Sound and along Penetanguishene Harbour before connecting to on-road routing out of town. The final piece of trail riding along the Rotary Waterfront Trail brings you into Midland, the final destination of Day 1.

Day 2: Midland to Orillia – 54km

Area services along this section of the route: Accommodations, cafés, restaurants, grocery stores, shopping, banking, bike shops (in Orillia and Barrie), attractions, wineries and trails.

Connecting to the route and trail in the morning, from your accommodation ride to the intersection of King Street and Bayshore Drive, where the MIdland Rotary Trail trailhead is on the northside of road. Enjoy the stunning views and shoreline riding along Georgian Bay. A short 7km in and located just off the trail is Sainte Marie among the Hurons, a Canadian National Historic Site and the site of Ontario’s first European community. Pubic washrooms located onsite. Set off riding along the fully paved Tay Shore Trail for 18km, part of the Trans Canada Trail. Enjoy frequent water views and water access between Midland to Waubaushene as this trail hugs the shoreline of Georgian Bay. South of Waubaushene connect on to the Uhthoff Trail before taking a break in the town of Coldwater approximately 24km into the day’s route and with several cafes, restaurants and a grocery store as well as some great antique shops. From here enjoy the final 25km into Orilla along this easy riding, primarily gravel rail trail. Cruise into Orillia enjoying views of Lake Couchiching before reaching the lakeside Couchiching Beach Park with its dock and sandy beach areas. After lunch choose between continuing south for 37km to Barrie or staying in Orillia to explore more with a visit to the Leacock Museum and National Historic Site, stop at the beach, shopping downtown, or to enjoy a post-ride patio break.

Day 3: Optional Extension – Orillia to Barrie – 37km

For those interested in riding on to Barrie, the route follows the Lake Country Oro-Medonte Rail Trail for 28km of easy riding on flat gravel surface. * There are frequent opportunities to cool off with a dip in Lake Simcoe at any one of the many beaches just a short detour off the trail. Enjoy the final 9km of waterfront riding along the Barrie North Shore Trail. * End the ride at Heritage Park along the shore of Lake Simcoe. Lock your bike and explore Barrie’s shops and restaurants located close to Heritage Park or sit lakeside in the park and relish in the fact you’ve completed a fantastic weekend of riding!

Note – This is not a looped itinerary!

It is suggested to always organize and/or confirm reservation and timing of transportation services prior to departure to ensure availability. Call local taxi companies to arrange pick up time, location and passenger numbers:

For larger groups, chartering a bus for bike and rider transportation is an option: Landmark Buslines, ,705-722-6666

Additional Information

Getting To/From Start: Parking is available at Grenfel Community Hall. For multiday parking permits please contact 705-728-4784. Riders who would like to take public transit can start the ride in Barrie and take the GO Train from Toronto to Barrie. Visit for information about schedules and fares.

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


As part of Canada’s 150th celebrations in 2017, Ontario 150 Celebrate by Bike connected fifteen communities across Ontario through cycling. Ride itineraries, events and cycling education in Bike Friendly Communities and Ontario By Bike ride destinations were developed and hosted to take advantage of the iconic Greenbelt Route and Great Lakes Waterfront Trail to strengthen communities and create cycling itineraries as a permanent legacy of Ontario 150. This initiative was a collaborative partnership between the Waterfront Regeneration Trust, the Friends of the Greenbelt FoundationOntario By Bike, and Share the Road Cycilng Coalition, building on two decades of investment in cycling infrastructure in Ontario. Check out the 15 legacy ride itineraries, and make plans to get out there to explore more of Ontario By Bike.

Ontario 150 Celebrate by bike