First Imperial Century on the Simcoe Loop

If you take your bike on GO Transit to Barrie, there are three main trails you can get to. Among these, I rode the Thornton Cookstown Trail last year, as well as the Barrie-Collingwood Rail Trail back in May. This left the Simcoe County Loop Trail which Helen and I did a small part of it from Barrie to Orillia back in 2019. Yesterday, I finally got to complete that Simcoe loop which also marked my first Imperial century ride which is 100 miles or 160 kilometres.

Barrie to Collingwood by Rail Trail

On April 30, 2026, Simcoe County officially opened the Barrie-Collingwood Rail Trail extension from Stayner to Angus. Before then, there was the 12-kilometre Clearview Collingwood Train Trail which was renamed when the extension opened. With Victoria Day being a nice day – but hot with temperatures exceeding 30’C – I brought my bike on the GO Train to Barrie to check it out.

Barrie to Brampton - Part 1 (Thornton Cookstown Trail)

One trail I wanted to do for a while was the Caledon Trailway. However, I noticed on Strava Joric did a one-way ride from Barrie to Brampton in June 2023 using that trail plus the Thornton-Cookstown Trail which prompted me to consider that ride as a follow up to the Kitchener to Hamilton ride in July 2023. Yesterday, I finally crossed that Barrie to Brampton ride off my bucket list! Part one of this series covers the Thornton Cookstown Trail and the second will focus on the Caledon Trailway.

Biking Barrie to Orillia

Since moving to the Greater Toronto Area in 2008, the only GO train line that was easily accessible outside of rush hour was the Lakeshore line from Oshawa to Aldershot (just outside of Hamilton). However, GO Transit has expanded service on its Barrie, Kitchener, and Stouffville lines in recent years as part of their Regional Express Rail program. This includes year round weekend service to Barrie in December 2016 and to Niagara Falls since August 2019. Having gotten curious to check out the Oro Medonte Rail Trail, Helen and I brought our bikes on the GO train to Barrie last weekend to try it out.

Barrie's old Allandale train station