Self-guided, supported trail and road tour over 5 days. It covers the famous 160 kilometre Simcoe Loop Trail as well as some extra jaunts along Georgian Bay and the Severn River. Experience quaint villages, lakeside accommodations, historical sites, and much more.

All multi-day tours are booked through our booking partner and licensed TICO agent

OK Cycle and Adventure Tours
666 Kirkwood Avenue - Suite B102, Ottawa, ON K1Z5X9
Toll-free 1-888-621-6818 or Local 613-702-5350
TICO Ontario Registration #50022848

Duration: 5 days/ 4 nights
Approximate Distance: 275 km (186 miles)
Cost: $1199 CDN per person + HST ($1354.87 CDN)
double occupancy; p
rice includes booking fee
Single Supplement: $395 CDN+ HST ($446.35 CDN)
Skill/Fitness Level: Intermediate 
Trip Departure
: Barrie

2021 Tour Dates:

July 12-16
August 30 to September 3
September 20 - 24

Custom dates for groups of 4 or more



  • 5 days/4 nights accommodations
  • 4 breakfasts and 1 lunch
  • Maps and GPX files
  • Luggage transfers
  • On call support service
  • Not Included: Airfare/transportation to route departure point, alcoholic beverages, personal expenses, gratuities.


  • Pick up/drop off at Toronto Pearson Airport
  • Bike rental
  • Extended bike and/or bike box storage beyond trip dates

Explore Ontario's Premier Cottage Vacation Destinations


Barrie to Orillia 

Day one begins in Barrie, and a trip along the Simcoe Loop Trail. Pass through Shanty Bay, Oro Station, and Hawkestone before finishing in Orillia for a night at the Champlain Waterfront Hotel.

Distance:  50 km (31 miles)


Orillia to Port Severn

Continue along the Simcoe Loop Trail, through the village of Coldwater and to Waubashene. Then divert north on quiet roads to Port Severn to Rawley Resort on the water, where the Severn River meets Georgian Bay.

Distance:  50 km (31 miles)


Big Chute Marine Railway and on to Midland

Today's ride takes you on a diversion to  Big Chute Marine Railway National Historic Site, back out to Georgian Bay and on the Tay Shore Trail to Midland.

Distance:  80  km (50 miles)


Awenda Park Loop

A loop from Midland through Awenda Provincial Park and back for a second night in the bustling town of Midland. Lots of Georgian Bay today!

Distance:  47 km (29 miles)


Midland to Barrie

Back on the Simcoe Loop Trail to finish the trip. Pass through Perkinsfield, Wyevale, Elmvale and Anten Mills before making your way back to Barrie to end the trip. Finish up with a celebratory group lunch!
Distance:  50 km (31 miles)


 Notes: Routes are subject to change without notice based on local conditions and guide judgement. Trips will run with as few as 4 guests.