Road Cycling Trip: Cycle from Parry Sound, Georgian Bay to Muskoka Lakes District and back to Georgian Bay through Port Severn, Midland, and Collingwood. Enjoy the rugged beauty of the Canadian Shield, the sweet water sea that is Georgian Bay, and the tranquil lakes and forests of Muskoka. Discover ghost roads, First Nation’s history, and experience cottage country culture.


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

OK Cycle and Adventure Tours
Katherine Morewood, Office Manager, Licensed Travel Agent
66 Kirkwood Avenue - Suite B102, Ottawa, ON K1Z5X9 
Toll-free 1-888-621-6818x102 or Local 613-702-5350x102
TICO Ontario Registration #50022848

Duration: 6 days/5 nights
Total Distance: 400 km (248 miles)
Cost: $1949 CDN plus HST  ($2202.37) 
per person, based on double occupancy.
Includes Booking Fee.
Single Supplement: $660 CDN  plus HST ($745.80)

Skill/Fitness Level: Intermediate/Advanced
Trip Departure
: Orillia, van transport to Parry Sound. 

2018 Tour Dates:

July 8th - 13th (SOLD OUT)
August 12th - 17th (ONLY 4 SPOTS LEFT!)


  • 6 days/5 nights accommodations
  • Meals - breakfast (except Day 1), lunches, dinner (except Day 6), and snacks/drinks during rides
  • 2 boat cruises
  • Humdinger cycling jersey and water bottle
  • Van support and guides
  • Luggage transfers
  • Secure bike box storage
  • Detailed route descriptions
  • Not Included: Airfare/transportation to route departure point, alcoholic beverages, personal expenses, gratuities for guides.


  • 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


Parry Sound and 30,000 Islands

We will transport you by van to Parry Sound, a small town in the UNESCO Georgian Bay Biosphere Reserve.  See Georgian Bay and the stunning 30,000 Islands by boat in the afternoon, and then we will have a short test ride at the end of the day. Grand Tappattoo Resort is our accommodation for the evening.
Included: Lunch, Dinner, Boat Cruise
Distance: 20km (12 miles)



Parry Sound to Bala

Today we move from the “near north” of Parry Sound into the heart of Muskoka with its myriad of lakes, rivers, and windswept pines. We will follow the shores of Lake Joseph for most of the day and complete our trip in the quaint village of Bala, where Lake Muskoka empties into the Moon River. You will have time to poke around the shops here. Day 2 is also our chance to sneak in a second boat cruise on the Muskoka Lakes, time permitting! In the evening we will transfer by van to our accommodation, Sherwood Inn, and settle in for a couple of nights. 

Included: Breakfast, Snacks, Lunch, Dinner, Boat Cruise
Distance: 67km (42 miles)



Lake Rosseau Loop

Today’s ride is hilly with several short steep climbs and one long, gentle slope of approximately 4 kilometres. We begin by winding north with Lake Joseph to the west and Lake Rosseau to the east. We pass through Port Sandfield and Minett before looping around the top of the lake through Rosseau and past the Rosseau and Bent Rivers. Now heading south on the east side of Lake Rosseau, we end in Port Carling, the “hub of the lakes” at the junction of Lakes Rosseau and Lake Muskoka. Here we will explore the town, including The Wall photo mosaic, and eventually retire to back for a second delightful night at Sherwood Inn
Included: Breakfast, Snacks, Lunch, Dinner
Distance: 68km (42 miles)


Torrance to Port Severn

Day 4 is a challenging day of 120km, or you can take a bump along the way to make the ride ~80km. We begin with a very short van transfer to Torrance. The route includes Torrance Barrens Dark-Sky Preserve (albeit by daylight), Sparrow Lake, and the Big Chute Marine Railway (an inclined marine railway that carries boats up and down 18 vertical metres, the only one of its kind still in use in North America). We end the day by returning to Georgian Bay at Port Severn, and will dine and sleep at Rawley Resort
Included: Breakfast, Snacks, Lunch, Dinner

Distance: 120km (75 miles)


Waubashene to Collingwood

We will take things easy today! We start with a short transfer to Waubashene, and the begin our ride on the paved Tay Shore Trail. We will pass cottages, marinas, parks, wetlands, and have frequent views of Georgian Bay. We pass the historic Sainte-Marie among the Hurons and the Martyr’s Shrine. The trail ends in Midland, where we then head south to explore Georgian Bay’s famous sandy shores, including Wasaga Beach, the world’s longest freshwater beach. The last few kilometres of the day bring us into the four-season playground of Collingwood, where we will spend the last night of the tour at Pretty River Inn.
Included: Breakfast, Snacks, Dinner
Distance: 66 km (41 miles)


Collingwood Loop

Options, options, options! There are numerous possible rides from Collingwood. Depending on wind direction, the state of our legs, and group consensus, we may choose to loop over towards the village of Creemore, or head into Grey County and the town of The Blue Mountains. We will undoubtably cover some of the Apple Pie Trail, named one of the world's most enticing food and drink trails by CNN in 2017! Whichever direction we choose there are quaint villages, challenging climbs, and stunning view of Georgian Bay. This is our last day - we will wrap up the riding early so that you have a chance to do some shopping and site-seeing in Collingwood.  We transfer you back to Orillia and say our good-byes.
Included: Breakfast, Snacks, Lunch
Distance: 60 km (37 miles)

 Note that routes are subject to change without notice based on local conditions and guide judgement.