hey smiley...i always take my big hybrid (21" Schwinn) with the panniers to carry the tools, extra tubes, lots of water, and some food. Sometimes i need the rain gear too.
I try to do the ride in July, week 2 or 3...last year i think it was week 2, dry, but 40+C...even the asphalt was melting in places.
Usually go on a thursday to avoid the weekend traffic (last year i think it was a friday), leave Burnamthorpe/Kipling aound 8:00 AM, take a weird route to avoid airport road, but go through Caledon West, Alliston, Angus, and Wasaga...last year it took about 6.5 hours, 2 years ago 7.5 (rain with a strong headwind)...roughly about 140 km
company is welcome, problem is i usually don't plan ahead...if the conditions look OK, i just go.
Early this year Mrs. JM and I will be doing the Collingwood-Tobermory-Manitoulin Island-Sault Ste Marie-and back along Georgian Bay ride...then maybe off to Newfoundland this year or next
As you age, the stuff you do just gets weirder, so i'm told...getting more ideas from
www.crazyguyonabike.com to which i was referred to...check out some of the Ontario rides in the North America section
cheers
EDIT: the total ride is closer to 170 km as i'm in wasaga...i ride to my kid's place in collingwood, then go back to wasaga to meet Mrs JM who drives up later