I love history. Wherever I travel I am always stopping at the historical plaques and signing up for a walking tour. In my new ‘hometown’ of Toronto, it’s no different. So when the annual Jane’s Walk comes around, I load up my weekend with free citizen-led walks to discover new neighbourhoods and communities.

That was pre-kids. Now, with little walkers in TOw, it’s become much more difficult to make it through an hour-long hike and soak in all the interesting info uninterrupted. But this year I am determined to join my fellow curious Torontonians (and those in 160 cities around the world) through streets, alleys and trails for Jane’s Walk – May 1st, 2nd and 3rd – and to bring the kids along.

The free walking tours led by anyone and everyone come in all lengths, themes and destinations from nature and food to history and art. Many are “strollers welcome” and 268 of them in T.O. are deemed “family-friendly.” No pre-registration required.

Here is a handful that may intrigue the littler urbanites:

City’s Best Hiding Places: A Geocaching Tour!
Friday, May 1st, 4 pm
What kid will say no to a great big treasure hunt? When geocaching people hide little trinkets, stories and other interesting things and mark the general location on a map at geocaching.com. Jane’s Walk Denise Pinto will lead the way starting at Danforth & Donlands and end up at Monarch Park. Be sure to check out the how-to and tips before joining.

Connect Nature in Dempsey Park
Friday, May 1st, 12:30 pm
This 30-minute dose of nature in North York ties into the start of the David Suzuki 30×30 Nature Challenge. The bulk of the tour is at Dempsey Park where young and old can reconnect with the community and the Earth.

Under the Rainbow – Don Mills to the Rainbow Tunnel and the East Don
Saturday, May 2nd at 11 am
Okay, so the first stretch might be a stretch for the kids, but if you can keep them engaged from the Shops at Don Mills and surrounding neighbourhood, you’ll enter the Greenbelt and follow Moccasin Trail Park to a rainbow. Well, the “Rainbow Tunnel” which leads to the East Don Trail. 

Milkman’s Run – Castle Frank to Evergreen Brick Works
Saturday, May 2nd at 10:30 am 
This is super nature walk starts at Castle Frank Station goes through parks, gardens, laneways and trails to learn about how people and nature have interacted over the past 100-plus years. Whether you stick with the group or keep on trekking, you’ll end up at one of the best places in the city Evergreen Brick Works.

Graffiti in Toronto
Saturday and Sunday, May 2nd and 3rd at 2 pm
This one is less walk and more talk so may be best suited for older school-aged kids or teens in TOw. You’ll be led down a couple of the most colourful alleys in downtown Toronto near Queen St. and Spadina to take in and learn about graffiti in the city. If you’re bringing younger kids along, keep in mind this walk has attracted huge crowds.

Walk as a Workout
Saturday, May 2 at 10 am and 4 pm
This walk is focused on exercise in nature – so bring along the little ones to burn some extra energy as you explore the historic Humber River. No worries if you run ahead or lag behind. Starting point is Etienne Brulé Park.

Jane’s Walk School Editions
Kid-led tours also take place this week as part of some high school Jane’s Walk programs. There has been some Junior Jane’s Walk with primary school-aged aged children in the past. You can learn more here on how to participate and create your own kid-friendly walk.