
Photo: Town of Milton
It’s Street Name Monday!
On a weekly basis, we speak with local historian John Challinor II to gather information and details about the namesakes of our roads. If you weren’t aware, he and the late great historian, Jim Dills, wrote the book on Milton street names, writing Milton Streets back in 2007. Challinor also served seven years as the President of the Milton Historical Society.
Recently, we focused on Halm Road and Sydenham Lane. This week, we’re covering Hill Street and Stagg Garden.
Starting alphabetically with Hill, Challinor says the name comes from a former resident, rather than an incline in landscape.
It’s worth pointing out that there is technically a second ‘Hill’-named street in Milton. We covered the history of Kean Hill Drive here. Challinor says emergency services always have to sign off on street names that have similarities. The addition of ‘Kean’ to the name, along with the ‘Drive’ suffix made it acceptable to have both street names in the community.
Our second street this week is Stagg Garden. While it may sound like a beautiful meadow filled with deer, Challinor says the name actually comes from another local veteran who also had a pretty notable career here in Milton.
It was common back during the wars for soldiers to send letters to their families. A lot of those letters would also be shared with the local newspaper to help provide updates for residents. With Stagg being an employee of the Champion at the time, Challinor says he provided some local wartime reporting himself before he was sent home. He then returned to his role printing the paper, which he held for a very long time.
If you’re looking to understand how Milton’s streets are named, you should check out the book written by Challinor and Dills. Published by the Milton Historical Society back in 2007, it sold out in about six weeks and has since been long out of print. That said, according to Challinor, you can still find a copy at the Milton Public Library. With nearly 15-years having passed since the initial publication, and the extensive town growth in that time, an updated book is likely to come.
You can also take a walk with the late Jim Dills down Milton’s Main Street in 2002.
Have a suggestion on what you’d like to learn about next week? Let us know! We’re currently working on names that we find interesting. You can message our X account or email us at News1013@LocalRadio.ca. Otherwise, we’ll just continue asking about local street names that we find interesting.
If you have a news tip or story idea, you can now send us a heads up via email at:
- News1013@LocalRadio.ca (Milton)
- News1015@LocalRadio.ca (Orangeville)
- News92@LocalRadio.ca (South Simcoe)
- Rick.Sargent@LocalRadio.ca (Bolton)
If you’d like to get ahold of me personally, shoot me a message at Cameron.Wilkinson@LocalRadio.ca. We’re in the business of content creation, so no idea is a bad idea.






