an annual series of long rides on a two-wheeler
2026… Apr 26 – May 31 – Jun 20 – Jul 19 – Aug 23
Wasaga Won Hundred
Sunday April 26, 2026
100 km on terrific tarmac! a pre-season tour on roads around beautiful Simcoe County
route: https://www.strava.com/routes/3329491642442101504
9 am departure from Meridian Place, Barrie ~29-30 kph average pace
2025 results https://twowheelstonowhere.ca/2025/04/19/wasaga-won-hundred-2025/
Meaford Mixed Roads
Sunday May 31, 2026
a marvelous mix of tarmac, gravel and trails leading from Barrie to Meaford then up the Escarpment to some great gravel roads. Back to Barrie through Creemore. an epic 220k tour to start the season
route: https://www.strava.com/routes/3332054275792516544
8 am departure from Meridian Place, Barrie ~26-28 kph group pace
2025 results:
https://twowheelstonowhere.ca/2025/05/25/meaford-mixed-roads-2025/
Big Chute Loop
Saturday June 20, 2026
what the hell is a marine railway, anyways? join us on the journey from Barrie to Big Chute where big boats take the “train” up or down Lock 44, on the marine connection between the Severn River and Georgian Bay. stop both ways in Coldwater. 175 km
~30-32 kph group pace
route: https://strava.app.link/O9t9Po1qHPb
8 am departure from Meridian Place, Barrie
2025 results:
https://twowheelstonowhere.ca/2025/06/22/big-chute-loop-2025/
Hairshirt North
Sunday July 19, 2026
Mark your calendar today for this epic excursion on two wheels to nowhere!
320 kilometers of beautiful roads around Simcoe County’s lakes and waterways. Optional 230 and 140 kilometre routes allow riders of all fitness levels to participate. Pick your poison.
… and for those who love to suffer, a 400 kilometre option splitting off from the Hairshirt North route at Wasaga Beach to take in Collingwood, Thornbury, Creemore and Angus before heading home to Barrie. it’s what I call a Dawn to Dusk Durability ride. charge up your headlights!!
Here is the 400k honour roll!
check out the four Hairshirt North route options here – pick your poison!
140 km route ~ Escape Route #1 https://www.strava.com/routes/2842889022355412082
230 km route ~ Escape Route #2
https://www.strava.com/routes/2842228638624274408
320 km route ~ Hairshirt North
https://www.strava.com/routes/16468099
400 km route ~ Dawn to Dusk Durability
https://www.strava.com/routes/3103756881387739136
Unsure about the challenge? Questions? Call or message me anytime 705-718-7760
6 am departure from Meridian Place, Barrie ~30-32 kph group pace
2025 results:
https://twowheelstonowhere.ca/2025/07/06/hairshirt-north-2025/
all my previous Hairshirt North results:
2017 https://www.strava.com/activities/1076252024 (the ride that inspired the Hairshirt North)
2019 https://www.strava.com/activities/2532969425
2020 https://www.strava.com/activities/3686530601
2021 https://www.strava.com/activities/5613502502
2022 https://www.strava.com/activities/7448817674
2023 https://www.strava.com/activities/9465461289
2024 https://www.strava.com/activities/11833810440
2025 https://www.strava.com/activities/15031104225
other Hairshirt rides I’ve done:
2019 https://www.strava.com/activities/2475551164
2018 https://www.strava.com/activities/1660474309
2016 https://www.strava.com/activities/622123918
Southwood Road Ramble
Sunday August 23, 2026
a 230 km tour through Simcoe-Muskoka. swing-bridge over the Severn River, rocky lake views, cranberry bogs on a tour across Torrence Barrens on the edge of the Canadian Shield. lunch in Gravenhurst, then southward on the ruggedly scenic Housey’s Rapids Road and Cooper’s Falls Road to Washago for an ice cream cone. homeward along Lake Couchiching, through Orillia and back to Barrie along the Northshores of Lake Simcoe and Kempenfelt Bay
8 am departure from Meridian Place, Barrie ~30-32 kph group pace
main route, 228 km: https://www.strava.com/routes/2988536584054431250
escape route, 135 km: https://www.strava.com/routes/3255943099319517520
if you want a shorter 90 km option, turn back to Orillia at Burnside Line and the back to Barrie along Lakeshore/Ridge Rd
2025 results:
https://twowheelstonowhere.ca/2025/08/17/southwood-road-ramble-2025/
Two Wheels To Nowhere 