Self-guided 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.

2024 Tour Dates:

on hold

Custom dates available (conditions apply)

Interested in just the Simcoe County Loop Trail? Check out our 3-day version of this trip.

Duration: 5 days/ 4 nights
Approximate Distance: 275 km (186 miles)
Cost: $1099 CDN pp + HST ($1241.87 CDN)
double occupancy; p
rice includes booking fee
Single Supplement: $449 CDN+ HST ($507.37 CDN)
Skill/Fitness Level: Intermediate 
Trip Departure
: Barrie

Deposits & cancelations:
20% deposit at time of booking is transferable up to 60 days before trip departure. Full refund is available if we need to cancel due to changes in travel/Covid regulations.
Full details in FAQ


  • 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

We are partnered with 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


Barrie to Midland 

We will meet you just North of Barrie, to get your luggage and make sure you are all set to ride. You will pass through Anten Mills, Elmvale, Wyevale, and Perkinsfield before finishing in Midland on gorgeous Georgian Bay for the night. Midland has a very relaxing waterfront and many excellent dining options. Spend the night at the charming Dragonfly Dreams Bed and Breakfast.

Distance:  50 km (31 miles)


Awenda Park Loop

Today you veer off the Simcoe Loop Trail, and do a loop from Midland through Awenda Provincial Park. The Georgian Bay beaches make an excellent spot for a relaxing break and maybe a swim!

Enjoy a second night in Midland at the Dragonfly Dreams Inn.

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. There is an optional loop out to the Big Chute Marine Railway National Historic Site.  Tonight's accommodation is the very relaxing Rawley Resort.

Distance:  30 km (18 miles) or 78 km (48 miles)


Port Severn to Orillia

Returning to the Simcoe Loop Trail, ride to the Champlain Waterfront Hotel in downtown Orillia. You will pass through the historic village of Coldwater, which is a great place to have lunch. 

Distance:  40 km (24 miles) 


Orillia to Barrie

Lake Simcoe is just to the south for most of your ride today with several places for you to pop down to see the view and maybe have a swim. Pass through Hawkestone, Oro Station, and Shanty Bay before making your way through Barrie to end the trip where we will meet you with your luggage. 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.