I have found the most beneficial thing to my walks has been planning them out in advance. My primary tool is the same one I use to map my walks: Google My Maps. This can help with wayfinding when you’re out and about, ensure you keep the length of your walk manageable, and help you identify specific points or shortcuts to take. I highly recommend exploring any historical aerial imagery to find past features that have been lost, as well as current municipal GIS maps to identify public lands and easements.
Exploring your local metroscapes should be a sustainable matter. I encourage using transit to get to and from a walk, and the walk start / end should be planned at local transit stops.
If you are walking for more than 3 hours, plan a meal. This can either be something you can eat out of tupperware along the way, or picking a restaurant that you will pass on your walk around the time you want to eat. Be sure to pack some snacks as well. I recommend at least two things you can eat with your hands: something with protein, and something with some sugars; the former can fill you up and satiate your hunger, and the latter can give you an energy boost if/when you hit a wall of fatigue. My personal favourite snacks are crackers with peanut butter, as well as clementines.
Staying hydrated is important for your muscles on a hike, so make sure you take water with you during your trip, regardless of whether it is hot or cold. I like to start off my walks with a mug of coffee, but you still need water along the way.
Going to the bathroom can be a tricky affair to plan. Just like food, I would try to identify potential bathroom breaks along your walk.
Respect private property. As for public spaces, no trespassing signs and/or fencing should be your indicator that you should not enter.
Make sure your hiking is safe, and don’t put yourself in danger. This includes staying away from cliff edges, eroding banks and bluffs, and waterways during and after major rainfall or ice melting / jam events. Monitor warnings from your local conservation authority and municipal departments, and heed any signs that restrict access due to hazardous conditions.