I have come across websites that may be useful :

• Couch Surf
• Drive in Movies
• Hostel world
• Road Food !
• Roadside America
• Trip Cost Calculator

I have also put together a brief list of old roadtrip-esque movies to see: (I'm not backing these movies although a few are quite good)

• Bonnie & Clyde - 1967
• Bottle Rocket - 1996
• Cannonball Run - 1981
• Easy Rider - 1969
• Into the Wild - 2007
• It's a Mad, Mad Mad Mad World - 1963
• Little Miss Sunshine - 2006
• Motorcycle Diaries - 2004
• Smokey and the Bandit - 1977
• The Darjeeling Limited - 2007
• The Straight Story - 1999
• The Wild one - 1953
• Thelma and Louise - 1991

A Few Books I own:

• Road Trip USA
• Roadtripping USA
• Road Food
• 1,000 Places To See Before You Die <A Travelers Life LIST>

I have put together multiple play-lists by genre and road trip length but, I wont be posting such lists... however if anyone is interested in my Excel spreadsheet of supplies just let me know and I'll try to find it! lol