There are a lot of things to consider when you are choosing a walking route. Some of these things, ironically, you may not have considered so far. Here's a breakdown.
How far are you walking? (I mean, duh.) But what I mean is, is this a new distance for you? Are you nervous about going farther than you've gone before? If you are feeling a bit uneasy about your ability to finish, there are two ways to handle it. If you want to give yourself an out (due to injury, fatigue, whatever), consider doing multiple loops near your residence, or do a snake-style up and down side streets near your residence. That will give you opportunities to abort mission safely. If you want to push yourself and require completion of the entire distance, perhaps an out-and-back would be best. Once you get, say, 4 miles away, you will HAVE to come 4 miles back.
How's the weather? Generally speaking, you will want to be protected from the elements. Sun and wind are the "silent killers," and buildings and trees will provide more shade and wind blocking than wide open prairies and such. It is also wise to avoid lots of concrete in the heat, since it will make your path much hotter than it usually would be. Forests can also offer some protection from rain, if you're into that sort of thing, but I'd just wear a hat.
How are the road/trail conditions? In the winter, if you are in a snowy or icy area, you will want to take trails and pathways that are plowed/shoveled and salted or sanded to avoid slipping. If there is a trail that gets muddy or flooded and there has been a lot of rain recently, avoid that trail.
How safe is it? You will want to consider both safety from injury (avoid trails and sidewalks that are potholed, uneven, and neglected) and safety from crime. Avoid paths that take you too far from civilization for too long, because that may leave you vulnerable to any number of threats (such as wild animals and your own body collapsing and nobody around to call for help). Avoid areas that are dangerous or unsafe, rape and assault-wise. On that final note, ALWAYS LOOK ALERT when you are walking. Even if you feel like death, don't let it show on your face or in your body language. Avoid being a victim by avoiding looking like an easy target.
How hilly is it? Contrary to popular belief, flatter is not always better. If you are training for a race, try to find long-walk routes that are similar to your race course. If you are training for a marathon with a hilly first half, do your long workouts on a route with a hilly first half. If you are training for a pancake-flat half marathon, do your long workouts on pancake-flat trails. You want to get your muscles used to whatever terrain they will need to be used to. On the other hand, you should try to walk each week on a different style of terrain at least once, just to keep in good general walking shape.
Where do you like to walk? Urban vs rural. Forests vs lakes. Recreation trails vs sidewalks. There are a ton of options and every person is different. If you choose routes that you think are scenic and lovely, you will enjoy your workouts more. My six-mile short workout takes me past a golf course where I am motivated by occasionally finding golf balls. I've collected 8 of them so far. Whatever keeps you going, gang.
Are there any obvious issues with your route? You may not notice this until you try it, but various things like trains, unleashed dogs, farmer's markets, scary hobos, creepy people, cigarette smokers, and any number of things that may be along your route all the time can be avoided. Some of these things are one-time events, but some of these things may be a regular occurrence.
There are a couple of good mapping tools that I enjoy using:
USATF Map It - this lets you click out a course wherever on the map you want. It is my personal favorite mapping tool because it lets to create "shortcuts" (say, you can cross a grassy strip, or something) and it has mile splits that automatically show up.
On The Go Map - this is a very accurate mapper and will automatically fill in the gaps between your waypoints. Unfortunately, it does not allow for shortcuts, since it must stay on the street or recreation trail. This can also lead to occasional baffling moments when creating your route. If your route is very simple, though, this can be a great tool. No mile splits, sadly.
Once you find your favorite routes, it will be easy to feel motivated to get out there! Choose wisely!
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