Here is a suggested approach for the beginning barefoot hiker. First of all, if possible, spend some time in your front or back yard barefoot. Try a variety of surfaces. Take your time, look around and flex your toes gratefully.
If you have some local streets, parks or nature centers that are appropriate (not too much traffic or litter) you can extend your pre-conditioning to those areas.
Try to interpret the new sensations as just that, new sensations. At first, the unfamiliar textures overwhelm the tactile senses. The first ten minutes or so for a beginning barefooter can be the most difficult. You will be in a process of adjustment. Most find that after this time (sometimes just as they were about to give up), the going became considerably easier. Did you ever get too much wax (or some water) in your ear for a while, and then when you got it out ... all sounds seemed to be really LOUD. If you did, you'll understand what I'm saying. Perhaps, when you first take your shoes off, the ground is too "loud". It's like listening to a lot of uncomfortable noise. After a while, your body adjusts and you begin to "hear the music".
On your first few jaunts, you are going to spending more of your time than usual examining the ground in front of you for hazards. This is natural (you will also notice some things you had never seen before), but over time you will find that you need to look down less often and that on many surfaces a periodic glance will suffice.
As your feet thicken and strengthen, with confidence and technique building, the tension and alarm you may have felt earlier will dissipate.
For your first bonafide barefoot hike, select a short trail with a variety of surfaces. I recommend against using a trail with a long gravel lead-in for the first hike, since it is psychologically better to begin barefoot (and to leave the shoes at home, in the car or in the pack). However, if such a situation is not avoidable, consider the end of the gravel to be the beginning of the hike. Later, short to medium sections of gravel will be just another texture to you.
It's good to take along a friend who is either an experienced barefoot hiker or is willing to try along with you. If that's not possible, then go alone and take this introduction along as your companion. Until you have developed confidence in your bare feet, we recommend that you delay accompanying otherwise shod groups as a lone barefooter.
By the time you are finished that day, your feet may seem somewhat sore. One of the best things about barefoot hiking is the vibrant, tough and resilient feeling that comes into the feet over the next one or two days as this soreness dissipates.
On the next (and future) hikes you will find that you are able to go further and on rougher trails than before. "Mileage" will vary, but typically by following the above regimen, with short hikes once or twice per week and going barefoot outside (in general) as much as possible, you should be able to do four or five miles on easy to medium trails within a month or so. If you take trouble to find small-grade gravel paths in local city parks and work out on them ... the toughening process can be accelerated considerably.