Erin’s Trans Canada Trail: Chasing History and Fall Colours in Orillia, Ontario

Written by Erin Hynes 

Fall in Ontario is one of my favourite times to be outside in Ontario. I love that short window of the season when the air turns crisp and the trees show off their brightest reds and golds before winter arrives.  

So when I learned that the Trans Canada Trail passes right through Orillia, I decided to spend a day walking it, with the goal of soaking up as much autumn colour as possible. 

Tudhope Park to the Leacock Museum 

My partner and I started our morning at Tudhope Park, a quiet green space that stretches out into Lake Couchiching. The park has a lovely trail that runs through it, along the water. This trail is part of the Orillia Millennium Trail, an 8.25-km paved urban route that’s ideal for walking, hiking, and road cycling, connecting parks, waterfront views and cultural landmarks throughout the city. 

Photo credit: Erin Hynes, Pina Travels

The air was cool with a slight breeze, and the sun was out, making it a perfect day for walking. The trail followed the shoreline through the park, weaving through a mix of open parkland and clusters of trees that had already turned shades of amber and red. As we walked, we spotted lots of squirrels as well as geese out on the lake.  

It wasn’t long before we reached one of Orillia’s most notable landmarks on the trail: the Gordon Lightfoot sculpture, titled Golden Leaves. Lightfoot was born and raised in Orillia, and this sculpture pays tribute to his music and legacy.  

Photo credit: Erin Hynes, Pina Travels

It’s made up of large bronze leaves, each with lyrics from his songs engraved on them. There’s also a bronze guitar, and a figure of Lightfoot himself seated on a bench. It’s a peaceful spot to pause, especially if you grew up listening to his music in the car, like I did. Standing there, surrounded by fall colour and the sound of the lake, it felt like a fitting place to stop and take it all in.   

From there, we continued along the Orillia Millennium Trail toward the Leacock Museum, which sits right on the water. The museum is inside the former home of Stephen Leacock, the Canadian humourist and author.  

It’s a beautiful, white, two-storey house surrounded by lawns and big old trees. Inside, you can walk through rooms that have been kept as they were when Leacock lived there, with books, personal items and old photographs that give you a sense of what Orillia life was like in the early 1900s. There’s also a small exhibit about his writing and how this area inspired his stories. 

Photo credit: Erin Hynes, Pina Travels

It’s worth noting that the museum has seasonal hours, so if you want to visit, check ahead to make sure it’s open. Even if you don’t go inside, the grounds themselves are lovely to wander. The trail passes right by, and there are benches where you can sit and look out at the lake. 

Walking Along Lake Couchiching 

After visiting the museum, we followed the Orillia Millennium Trail as it heads to the centre of Orillia, toward Couchiching Beach. The trail connects several parks and public spaces along the water, and you’re never far from a good view.  

Photo credit: Erin Hynes, Pina Travels

Along the way, it’s worth stopping at the beach to take in the view of Lake Couchiching. In the summer, it’s a great spot for a swim or a picnic by the water. At the north end of Couchiching Beach, you’ll find a particularly beautiful stretch of the Millennium Trail, especially in the fall.

With trees arching over the path and leaves turning every shade of gold and orange. When we were there, the colours were so vivid it felt like walking through a painting. I definitely recommend pausing here for some pictures! 

Photo credit: Erin Hynes, Pina Travels

Wrap Up Your Day on the Uhthoff Trail 

Eventually, we made our way back to the car and decided to check out another nearby section of the Trans Canada Trail, about a 15-minute drive outside of town: the Uhthoff Trail. 

The Uhthoff Trail is a 32 km trail in Ontario that runs from Orillia all the way to Waubaushene. This portion of the trail has a different feel. It’s part of the old CN rail line that once connected Orillia to other communities in Simcoe County.  

Today, the route is a quiet, mostly flat multi-use trail that passes through farmland, wetlands, and forest. The surface is crushed gravel, easy for walking or biking. 

We parked in a small, free parking lot at the corner of Division Road East and Carlyon Line. From that parking lot you can easily access the Trail.  

Along the Uhthoff Trail, interpretive signs share bits of local history and ecology, pointing out how this former railway corridor now supports a healthy mix of habitats. We saw a few cyclists, a couple of dog walkers and one person out birdwatching. It’s the kind of place where you can go for an easy hour-long walk or spend the entire afternoon exploring. 

By the time we looped back to the car, the sun hung low and the light had that warm, golden quality unique to autumn. 

Enjoy Dinner in Downtown Orillia 

After a day of enjoying the Trans Canada Trail in and around Orillia, pop into downtown Orillia for dinner. We headed to a cozy local favourite, the Hog & Penny. After a day on the trail, the hearty pub fare and welcoming atmosphere at the Hog & Penny made for the perfect end to our Orillia adventure. 

Spending the day on the Trans Canada Trail around Orillia was a reminder of how easy it is to find beautiful, accessible nature close to home. The Millennium Trail gives you a chance to see the city’s lakeshore and cultural landmarks, while the Uhthoff Trail lets you enjoy a quieter rural setting.  

October might just be the best time to explore this part of the Trail. The colours are at their peak, and the weather is cool enough for long walks. If you’re looking for an easy day outdoors that mixes a bit of local history, culture, and plenty of fresh air, Orillia’s stretch of the Trans Canada Trail is a perfect choice. 

Erin Hynes is a travel blogger, podcaster, and content creator based in Toronto, Ontario. She focuses on traveling Canada, but has also traveled to six continents and lived abroad in two countries, experiences that inspired her passion for responsible, community-oriented tourism. That perspective shapes her work on her blog, social channels, and her podcast Curious Tourism, where she talks with thought leaders about making travel more thoughtful, ethical, and sustainable. Read more at www.pinatravels.org 

Main photo credit: Erin Hynes, Pina Travels