In July of 2008, we (Elizabeth, Paz, Benson, and Myself) took a road-trip from Boston to Mountain View to bring Elizabeth's shiny new car out to the Bay Area. We learned quite a bit about what to do and not to do on road-trips, and some of that accumulated knowledge is below.

Nothing below is rocket-science. If you give any thought to any of these topics, you're likely to arrive at the same conclusions. The purpose of this page is to incite thought, and give you the benefit of my experiences.

• Jungle Juice -- We ran into a lot of mosquitoes in Teton National Park, and wished we had brought some of this stuff with us. We had some bug repellant, but it wasn't nearly as strong, didn't last as long, and took up a lot more space.
• Small Cooler -- Eating-out was one of the largest components of the budget on our trip, even after eating food we bought in grocery-stores most of the time. Consider this point, as well, many of the places that we chose to stop for lunch/dinner/breakfast were much prettier than any restaurant in the area.
• Chuck Norris -- He doesn't like to be told what to do.
• Spare Laptop Battery -- Didn't use it...just took up space.
• Laundry Detergent -- We could have left this stuff at home. We only did laundry a couple of times, and always had the ability to buy it on the road.
• Shampoo etc. -- You find this stuff on the road, don't bother bringing it with you.
• Camera -- I have a Cannon SD 1000 digital camera that takes mpeg2 videos of extremely high quality (max quantization of ~20 or so). The form-factor of the camera was such that I could take it anywhere with relative ease (hiking in the parks, running in chicago, anywhere). I had an 8GB SD card installed in it that allowed me to take up to ~1hr of video. The camera took extremely high quality images, videos, and had spectacular battery life (one charge lasting ~1 week). Image stabilization would have been nice to have, but the form-factor and versitility of the little camera made it a great asset.
• Small tripod. Many of the videos taken were a bit shakey, and we speculated that a small tripod with flexible legs would have made a significant difference.
• Diary. This item is a bit personal. I've tried, on numerous occasions, to keep a diary -- with little success. I had always heard that diaries were for writing deep, reflective, innermost, blahdy blah blah blah. Given that seriousness isn't really my thing, I decided to try something else: silliness. I was with a rather silly crowd to begin with, making the process simple. The result was that writing in the diary was fun, and happened with great regularity. I took a Moleskine notebook with me that could be carried in my pocket. I also used the diary as a general notebook (jotting down possible activities, phone numbers, etc.) In the past, I've used < 10 pages on any given trip in any given diary; 50% of the road-trip diary was filled with inside jokes and notes of where to go and wwhat to see.
• FM/Cassette/Foo Adaptor -- We brought an Ipod, an XM Satellite Receiver, and a laptop with us on our trip, and we were able to listen to any of the three by simply hooking it up to the FM adaptor.
• ~5 Music CDs -- Every now and then, there would be so many FM stations in the area that the FM adaptor we brought with us was completely ineffective. Having a few CDs with you for those times when your adaptor doesn't work and/or you just don't feel like dealing with it, is a good fallback strategy.
• Books on Tape -- Music is nice to have, but it doesn't really engage and entertain your mind (well, my mind anyway) the way a story does. Books on tape are an amazing asset for a long trip. If you're going to be travelling by a lot of Cracker Barrel Restaurants then you might consider renting tapes from them, as they will allow you to return them to any restaurant along the way.
• David Sedaris -- Pablo Francisco, Dane Cook, Robin Williams, ...
• GPS -- For times when you really don't feel like navigating, and just want to get there, a GPS unit is invaluable. We had an el-cheapo (making its ROI tremendous). You don't even need a fancy one, something basic will do. You can make the argument that a really nice one can be used for looking up restaruants, etc., but if you have a smart-phone and/or mobile-broadband-enabled laptop, you'll have access to that information anyway.
• Atlas -- It isn't always just about getting from one place to another. On multiple occasions, we used our atlas to find county/state roads that paralleled our route and were much more scenic. Atlases are also fantastic for obtaining an overview.
• Frisbee -- baseball gloves, yard darts, thermonuclear weapons, etc... something to play with (preferably relatively small)
• Beautiful Girl -- Is there ever a bad time for one of those?
• Smart-Phone with GPS -- I had a crackberry 8000 series with GPS and google maps, and it was incredibly useful.
• Towel -- Simple thing to have in the cab of the vehicle with you, but amazingly useful as a blanket, pillow, lap-protector, sun-shield, etc...
• More Than 1 Duffel / Person -- PACK LIGHT!
• Sandals -- If you're the type that wears shoes most of the time (as I was on my first West-Trip), you might not think of this one.
• Backpack -- I had a full-on backpack that was good for carrying a lot of items around town (such as when we toured Chicago), and Elizabeth had one of those nylon sacks with two cords that you see a lot of teenage girls using. I'd recommend taking one of each.
• Power Inverter -- Having 110VAC in the car is handy for charging the laptop, cameras, phones, etc...
• DVDs -- I thought DVDs might be useful for getting us through the Eastern half of South Dakota, etc... but they weren't used, at all, and ended up just taking up space.
• Laundry Bag -- Simple little thing, but if you don't know which clothes are clean, and which are dirty...
• Assortment of ZipLocks -- Again, might not think of it, but they're nice to have (the slide-locks are nicer).

• Be Silly -- This point is, obviously, relatively personal. My compatriates and I are all pretty fun-loving and silly to begin with, so it worked out well for us.
• PACK LIGHT -- The more time you spend dealing with...stuff...the less time you spend seeing the sights.
• Turn the camera on the car
• Buy fuel outside of major metropolitan areas
• Eat food that you buy in grocery stores
• Do your homework on prices
• Over-estimate the budget
• Couch-Surf

Pack light. Please allow me to restate with proper emphasis: PACK LIGHT! Put some thought into minimizing little things like chargers. My crackberry, for example, is charged via mini-usb, which also happens to be how my camera's data is accessed. I have a laptop, so adding in one mini-usb cable allows me to charge my phone, and pull data off of my camera.

Partition your items when packing. Benson did a much better job than I, and my lack of proper partitioning became a pain after a very short time.