Walking Tours: Explore the History of Your Town

Posted : January 2, 2021

Our blog is chock full of great ideas for fun things to see and do in York Durham and Headwaters. We are always adding new content and updating old posts, but sometimes you might stumble upon something from our vault. If this article has inspired you to hit the road, be sure to double-check that the featured stops in this post are still welcoming visitors.

There are many things we can say about the culture and character of York Durham Headwaters. We’ve got the best of both worlds when it comes to small-town charm and thriving metropolitan entertainment. We’ve got world-class festivals and events and fine dining opportunities that will suit any palate and preference. Unfortunately, with COVID-19 affecting so much of what we do on a day-to-day basis and, more importantly, how we do it, we cannot yet experience all that YDH has to offer… at least as fully and freely as we once did.

But don’t hang up your hats and hunker down just yet. There are still plenty of things we can get out and do in the meantime. One of these things is explore the history of our towns on a walking tour. Our towns have so much interesting history, and many of the buildings and neighbourhoods we come across daily have fascinating stories. Our municipalities, local organizations and regional interest groups have worked hard to collect and preserve these stories in a format that people can experience any time. Here are a few of the walking tours we have in our region that you can explore at your own pace to find out what hidden history lies in your town.



One of the most comprehensive walking tours we have is in Durham Region: the Municipality of Clarington, to be exact. They have developed several self-guided walking tours that invite you to the hamlets and towns of Tyrone, Bowmanville, Orono, Newtonville, Newcastle, Jury Lands and Solina. Each tour is accompanied by a downloadable online brochure with pictures and a map for a fully integrated experience.

“Each community is unique,” says Laura Knox, Tourism Coordinator for the Municipality of Clarington. “There is a lot to learn and a lot to share. Our walking tours tell the history of our community. It’s really neat for everyone to learn—not only for history buffs, but for our residents as well. Getting them engaged and interested in rediscovering their community is a priority for us. We want them to have pride in residing here and to be able to tell the stories of where they live.”

The tours were initially developed over five years ago and were collaborative efforts between different groups within the region. The aim was to showcase some of the iconic heritage buildings that locals see every day as they go about their lives. The original tours focused on four of Clarington’s major downtowns and were later expanded to include other nearby locations.

One of the most popular tours is the Jury Lands Tour. If you are familiar with Clarington, then this is the site of the infamous Camp 30, where high-ranking officers of the Third Reich were held prisoner during the second world war. Before that, the campus was a school for truant boys. Though the Jury Lands are currently owned by a private developer, they are available for the public to explore as long as respect is maintained. “The Jury Lands Foundation have been great advocates for that property, as well as the history and the significance of it to our community,” Laura explains. “People come from all over to discover the heritage and the history of Camp 30 because it’s so interesting.”

Camp 30 Tour
Camp 30
Bowmanville road Tour



Step back in time and discover Orangeville’s history through one of three historical walking tours—or walk all three if you’re up for it. Start your journey by downloading the Footsteps from Our Past brochure, or pick up a hard copy from the Orangeville Visitor Information Centre. This guide will provide you with the three tours and everything you will need to know as you embark on them.

The Booming Broadway walking tour takes you on a journey of the businesses that helped the Town of Orangeville grow. This tour is 2.2 kilometres, and features landmarks such as The Orangeville Town Hall and Market, Castle Leslie and the Monument Works.

At 2.5 kilometres, the Founders tour celebrates the founders of the Town of Orangeville. Be prepared to learn about featured landmarks like the Canadian Pacific Railway Station and the Orange Jull House.

And finally, the Prosperous Years tour is a two-kilometre tour that takes you along Zina Street with a focus on the success of local merchants and business people. Featured landmarks along this route include the Land Registry Office and the Row Houses.



Soak up the stories of years gone by with Uxbridge’s Historical Walking Tour. You will get to explore thirty-seven destinations as you pass through residential neighbourhoods and the historic downtown core. See where merchants, doctors, beekeepers, carriage makers, shoemakers, masons and politicians lived. While you’re taking in all the architecture and history, take a break to shop and dine this beautiful town.

Like Clarington, this walking tour also has a downloadable online brochure for your information. Included on the walking tour is Uxbridge’s iconic York-Durham Heritage Railway, which hosts wonderful events all year long—so be sure to stop in and check what they’ve got going on.

More Walking Tours in YDH

There are plenty more walking tours to consider that explore the history of York Durham Headwaters. Get out today for a stroll and learn about the history of your own community.

Kleinburg Walking Tours

Richmond Hill Museum of the Streets

Jackson’s Point Walking Tour

Whitchurch-Stouffville Heritage Walking Tours

Downtown Erin Heritage Walking Trail

Hillsburgh Heritage Walking Tour

Plan ahead and safely. Please check with all the businesses for hours of operation and protocols.

Story by Katherine Ryalen

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