For the average budget traveller, living on the road means sleeping in cheap hostels every night. While there is nothing wrong with this when you're travelling by public transport, there are several problems with trying to hitchhike between hostels.
First, the cost. The price of hostels varies widely from place to place, but, even if you consistently find places that are very cheap, the total amount of money spent adds up quickly. Sleeping every night in $15 hostels for a month is still $450. The true cost of a hostel is not just the price of the bed either. It's easy to get caught up in the spending habits of other travellers and suddenly find yourself eating out every evening and drinking your money away in the nights, only to wake up one morning to find your wallet empty and your new friends already on their way to a different city.
Cheap hostels also have the downside of being in undesirable areas of the city. You're probably more vulnerable as a traveller walking back to your hostel late at night through a rough area than when you're camping quietly in the woods at the edge of the city, and it's not uncommon to hear of people who have had their possessions stolen from their less-than-secure shared rooms. The comfort of these rooms can be questionable, too, often suffering from ageing mattresses and loud noises – either from the bar downstairs, the traffic outside, or the snoring of your room-mates. Of course the vast majority of hostels are safe enough, comfortable enough, and very enjoyable to stay in – but it's worth remembering that you aren't guaranteed these things just because you're paying.
Finally, and most importantly, hostels are simply inconvenient for hitchhiking. If you book ahead, you'll suddenly feel under pressure to reach a certain destination each day. If you don't book ahead, every evening is spent wandering a city looking for a vacant bed at a good price. Either way you're guaranteed to waste time each morning when you have to make your way to the edge of the city to start hitchhiking again.
At this point, the experienced budget traveller might suggest couch-surfing as a good alternative to hostels. Although undoubtedly cheaper than hostelling, couch-surfing suffers from many of the same issues, namely the pressure to reach certain places by certain times. The main disadvantage is the effort required to organise a place to sleep: access to the internet can be sporadic when you're hitchhiking (unless you have a smart phone), and you have to be able to predict where you're going to be at least a few days in advance (which is generally difficult when hitching).
That said, for shorter journeys of perhaps less than a week, it is possible to overcome the difficulties presented by hitchhiking between hostels and couch-surfing hosts. You can make it work for you. It can be nice to stay in a hostel every once in a while on longer journeys too, when the possibility of doing laundry and taking a shower outweigh the other inconveniences.
Most of the time, though, the better option is simply to camp outdoors.
Many of us have gone camping, but the idea of pitching a tent outside of a camp-site can seem like a criminal offence to some. At the very least, free-camping can feel like a dangerous prospect to people who have never experienced it. And it's true that sleeping outside in a big city (or even a small town) has its risks and discomforts. With good judgement, however, there's no reason why your nights on the road should be anything but comfortable, restful, and reasonably safe. As with hitchhiking, the skill is in finding a good spot.
A good sleeping spot is discreet, somewhere out of the way, a place where you won't be noticed by other people during the night. Safety is the most important criteria. I prefer wooded areas, away from footpaths and ideally hidden from the road. If you're in a densely populated area when darkness falls, consider taking local transport somewhere a little more rural. If you absolutely have to camp in a city, look for large parks or playing fields. These are usually emptier than you'd think, but it's a good idea to scope them out in the daytime. Give a wide berth to any areas that show signs of settlement by the homeless. Establish your sleeping place after nightfall, away from street lamps or other light sources, and don't make a lot of noise or use a torch or phone once you've set up camp.
When most people camp outside, they imagine big tents and camping stoves. Free-camping is different. A tent is essentially a thin wall that blocks out your awareness of your surroundings, transforming normal, innocent night-time sounds into imminent threats of rape, murder, or animal attack. It's also a hassle if you need to leave an area quickly. Sleeping in a bivi bag – a large waterproof bag that you use to protect your sleeping bag from the dirt and rain – is much better in terms of convenience, situational awareness, and discretion. Try not to cook in the evenings, as the light and noise can attract unwanted attention, and the smell can attract animals in more rural areas.
If you do have an encounter with a stranger during the night, remain confident. People are conditioned to be scared of each other during the night time and you can use that to your advantage. Don't be aggressive, but firmly assert that you have to sleep and want to be left alone. Sometimes people will try to give you money or share something with you – it's often easier just to let them share it and then send them on their way. Pretending to be asleep or otherwise ignoring someone who is trying to get your attention can just make them even more determined to interact with you. Holding eye contact and keeping a neutral expression is a much more effective way to discourage them. After the person who is bothering you leaves, make a decision as to whether or not you want to stay in the same place or move on.
The second main criteria when choosing a sleeping spot is comfort. This largely depends on your ability to stay warm and dry, especially if you're in a bivi bag. Ideally you should try to find shelter from the wind and the rain – even a small bush can make a big difference – but just as important is the ground upon which you sleep. Concrete is hard, cold, and soul-destroying to sleep on. It should be avoided at all costs. On the other hand, tall grass, pine forest floors, or a sandy beach can rival the comforts of even the most expensive memory foam mattresses. The Earth will suck out your heat energy no matter what terrain you're sleeping on, however, so it's important to carry a mat to insulate your body from the ground.
You may occasionally find yourself sleeping in colder conditions than your gear was designed for. You can improve your situation by purchasing a hot water bottle and filling it with boiling water each night. Keep it close to your body, wear a lot of clothes, and wrap your shoulders in your towel/blanket – it's enough to get 8 hours of sleep. Wear multiple socks or wrap your feet with some dirty clothes to reduce icy-feet syndrome.
Be aware that large rivers or lakes sometimes create a lot of moisture in the surrounding air even if it doesn't rain and look for tide markings if you want to camp on the beach without being swept away. Remember to find shelter for your backpack as well as yourself and consider researching and taking appropriate precautions against wildlife – particularly bears.
If you make good judgements when it comes to comfort and safety, then there's no reason why you shouldn't be able to relax and enjoy a good night's sleep every night. In fact, you may find yourself so comfortable with free-camping that you start struggling to get out of “bed” in the mornings. In theory it's a good idea to pack up your camp-site early to avoid unwanted attention, but most of the time the only people who see you are early-morning joggers and dog walkers and they tend to leave you alone (although their pets may not). When you do eventually leave, remember to take all your rubbish with you.
If you're in a rural area and you're the kind of person who doesn't mind asking, you may have some success by knocking on people's doors and requesting to camp on their property. Farmers are more often open-minded about this and may have actual buildings to let you sleep in. (If you haven't slept in a barn yet, put it on your bucket list – there are few things as warm, dry, and comfortable as a large pile of hay, so long as you don't suffer from allergies.) Independent hostels or bed and breakfasts can sometimes allow you to camp on their land for free and I've heard of some hitchhikers asking to sleep in the gardens of normal, everyday people, although I've never plucked up the courage myself.
If you make friends easily, and you're confident in your judge of character, there is also the option of asking the people you meet if you can stay with them. The major advantage of this method is the possibility of regular showers. You'll be amazed at how quickly people form trust and how extensive their hospitality can be. This works best when it happens naturally – perhaps your last ride of the day was with someone who really enjoyed your company and they offer you their couch when they find out you're camping outside. Carrying a sign with the words “Looking for a sleeping place” while you walk around town can also be surprisingly effective. It's like hitchhiking, but with sofas instead of vehicles and you'll also get lots of advice from people about safer places to camp, cheap hostels, and so on.