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.

In order to finish the trail at a decent hour, I woke up at 5 AM to take the 6:12 AM bus to East Gwillimbury and then switched buses to Barrie. Fortunately, the bike racks are very secure.

I then headed towards the Spirit Catcher where the Simcoe County Loop Trail begins.

The wayfinding for this trail is very well marked, though there were a couple of minor issues. I also uploaded a map to my Garmin for the first time for an added peace of mind.

After going up a steep hill along Ross Street and Sunnidale Road, I then turned on to Anne Street. That street dead ends for cars per the below photo, but cyclists can continue to go through. Past this point, there were some steep descents and sharp turns before reaching Snow Valley Road.

I got to the North Simcoe Rail Trail after a speedy descent down Vespra Valley Road.

After Crossing Highway 26 – which seriously needs a safe highway crossing – I came across this gazebo which paid tribute to those who helped put the North Simcoe Rail Trail together.

Compared to the other trail segments, I found the North Simcoe Rail Trail needs the most work. It could use more detailed wayfinding signage and amenities such as benches, though the gazebo did have a bike repair stand. Even so, the trail quality was very good throughout except for a short section just before Flos Road 6, while there were lots of apples which prompted me to grab one from a tree.

Unfortunately, the trail abruptly ends at Flos Road 7. Likely because the landowner refused to give up land need to fill the gap to Flos Road 8. Therefore, a short detour was needed.

Elmvale Heritage Park has a large picnic shelter, a small playground, and washrooms which were much needed. Some porta potties could also be found along other parts of the trail.

The Tiny Rail Trail is considerably better in terms of trail amenities including park benches and detailed wayfinding signs showing maps, distances, and cross street.

These signs are rather cheerful yet modern.

Shortly past Concession 12, Tiny Rail Trail becomes paved at this gate.

This trail segment has a lot of turns and rolling hills to make things interesting.

Despite the “trail end” sign, it continues through this tunnel and becomes the Penetanguishene Trail.

These waterfront views never get old. This is at Rotary Park where the trail is paved.

I like this mural found on Penetanguishene’s Main Street.

A stop at Café Kittyhawk is a must in Penetanguishene. I had a latte and croissant, while the staff were friendly and they even had a bike rack next to their establishment.

I took a wrong turn at Murray Road by descending along this trail and had to backtrack which added two kilometres to the ride.

The Mid-Pen Link goes to Midland, is paved, and has a good sized descent.

This milling plant has a mural painted on the side visible from the water.

Lots of nice homes along Midland’s waterfront. Even though the homeowners also have their own docks, the public can still bike through so everyone can enjoy it. A win-win!

One thing that drives me nuts about the Tay Shore Trail is these entrances with a pole in the middle and instructing cyclists to dismount. It’s a serious safety hazard.

I took some inspiration from Jun by brining some stroopwafels for this ride. About 87 kilometres in.

After passing Highway 400, the trail changes names again to the Uhthoff Trail and becomes gravel.

About 100 kilometres in, I pulled over at Em’s Café for a smoked meat sandwich. While Jun’s recent post showed it was a popular cyclist spot, it was less busy when I got there because they closed at 3 PM and I arrived a half hour before. Very good sandwich and I like having a patio next to the river.

I like how the Simcoe County Loop Trail provides e-bike charging stations such as this one in Coldwater. They also have one at Midland and at a parking lot in Penetanguishene.

Time to continue on the Uhthoff Trail. While I felt decent at Coldwater, the tiredness started to kick in between Coldwater and Orillia at about 115 kilometres in.

Here’s Couchiching Beach in Orillia. It – along with adjacent Centennial Park – is a nice place to relax.

On to the Oro Medonte Trail.

Unfortunately, the underpass at Highway 12 has a homeless encampment.

One thing I like about the Oro Medonte Trail is these ponds. Another one further on has some swans.

These wayfinding signs weren’t there the last time I was on the trail.

After a short stretch on road, there’s one last gravel path leading into Barrie.

At the Barrie Sign – near the Spirit Catcher – after having done that 160 km ride!

Before catching the 7:10 PM bus to Aurora and then the train home, I went into Downtown Barrie at Greek Guys to get a falafel wrap to go at Greek Guys. And for those asking, I already filled out the form on my way home to claim my shirt which Cycle Simcoe sends to those who biked the Simcoe Loop.

Overall, the Simcoe County Loop Trail makes for a unique challenge and is a good option for gravel riders with excellent wayfinding. Those of you who are less experienced or wish to spend more time in Penetanguishene, Midland, Coldwater, or Orillia may want to spread the trip over two days. Another thing I probably should have considered is to arrive at Barrie the night before instead of waking up super early.