Should I book my accommodation in advance?

This is down to personal preference - how much freedom do you want? Finding a place to stay is generally not too difficult, and most areas along Route 66 will be able to offer basic accommodation for the impulsive traveller. However, if you know in advance that you’d like to stay in a specific motel/hotel it’s essential to book in advance, particularly in peak season. Certain iconic motels will be fully booked months in advance. A sensible option would be to stay at a mixture of booked and spur-of-the-moment lodging; this way you get to balance the freedom of travelling the open road with the security of knowing you won’t miss out on the most iconic stops. Pick the motels you’d consider a must-see, book yourself a room, and fill in the remaining gaps as you go along. Spur-of-the-moment lodging at chain motels is particularly easy to find due to the high number of such establishments.