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)
2022 Cost: $1099 CDN pp + HST ($1241.87 CDN)
double occupancy; p
rice includes booking fee
Single Supplement: $415 CDN+ HST ($468.95 CDN)
Skill/Fitness Level: Intermediate 
Trip Departure
: Barrie

Tour Dates:

June 3-7
July 11- 15
August 15- 19
Custom dates available (conditions apply)



  • 5 days/4 nights accommodations
  • 4 breakfasts
  • Maps and GPX files
  • 4 Luggage transfers
  • On call route assistance
  • 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


Barrie to Midland 

Day one begins in Barrie, along the Simcoe Loop Trail. Pass through Anten Mills, Elmvale, Wyevale, and Perkinsfield before finishing in Midland for a night at the charming Dragonfly Dreams Bed and Breakfast.

Distance:  50 km (31 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 Port Severn

Today's ride takes you along the Tay Shore Trail to Waubeshene, and then back out to Port Severn on Georgian Bay for a night at Rawley Resort.

Distance:  30  km (18 miles)


Port Severn to Orillia via Big Chute Marine Railway

Returning to the Simcoe Loop Trail, today’s ride features an optional loop out to the Big Chute Marine Railway National Historic Site before moving on to finish the day at the Champlain Waterfront Hotel in downtown Orillia.

Distance:  50 km (31 miles) / 80 km (50 miles)


Orillia to Barrie

Pass through Hawkestone, Oro Station, and Shanty Bay before making your way back to Barrie to end the trip. Congratulate yourselves on a ride well done!

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.