Trips across the US playing an instrument, anyone?

What era is this set in? I know my boss started hitchhiking every summer when he turned 14, and would travel from one coast to the other, once even to Mexico and back. He just turned 70.

If you have a couple of places in mind where your MC is going to stop along the way, you might want to investigate whether or not that town has "busking" laws (whether or not someone can play an instrument in public), what it takes to get one if they do, and what the vagrancy laws are. If you know that, you can give your MC a little grief for either the music (if the town doesn't allow public entertainment by random musicians) or sleeping out in the town green/park.

Wiki link: http://en.wikipedia.org/wiki/Busking

Back in college, I did a lot of hitchhiking, since I didn't have a car. I didn't play an instrument, I just went around the Midwest to concerts or even museums. I hitchhiked about 100 miles to see a ballet. I have some stories, and if you think they'd apply, you can contact me. As I said, this was 40 years ago and I wasn't playing an instrument professionally.

I don't hitchhike personally, but I do travel around constantly (live full-time in an RV and frequently store it to stay in hostels, take train trips, etc). I've met a LOT of wandering musicians, just traveling around doing their thing. They usually travel through a combination of hitching, train-hopping (stowing away on a freight train) and bus. Sometimes they get enough money together to buy an actual ticket on a passenger train.

There's a group in pretty much every major US city (international, actually, but since your character's traveling the US...)They're known by many names, depending on who you ask...gutter punks, street kids, crusties (because they don't have a lot of opportunities to shower), travelers..... He'll get really good at finding them and making friends.

They'll share a little food and a little weed with him and bring him up to speed on surviving in that town. A lot of cities have shelters that serve free meals...in some places if you hang out in the town square long enough a nice Christian mission group will come by with sandwiches. If he's any good at hustling, he won't sleep on the street much...there's always crash pads and friends' apartments, he just has to be charming and/or amusing. He won't make a ton of money, but he'll make plenty to get by...it's a romantic life in a lot of ways.

The advice about checking laws on vagrancy, etc is good. Street kids get harassed a lot, because they're "bad for the city's image" or some garbage, but they rarely get locked up for more than a day or two. If you need him in jail for some reason though, it wouldn't be unrealistic.

Hope this helps!

If he's really good, he might be able to play clubs. Usually the kind of club that plays solo guitar doesn't pay, but they can take up a collection from the patrons at the end of their sets. They usually get free coffee and a free meal as well.