When Route 66 was established in 1926, it was one of the highways cutting across the U.S. diagonally. It was replaced by a highway between 1956 and 1984, then officially closed in 1985. Since 1999, it has been protected as a symbol of cultural heritage, and a Route 66 road trip is a fixture in popular culture, as well as one of the most iconic road trips in the U.S.
The route has gone through several changes and realignments. Some of it was minor, some more major. For example, an early Route 66 alignment in New Mexico cut through Santa Fe, but in 1937 it was rerouted to bypass the state capital. So today, road trippers have different options of which road alignment they would like to take. This guide to a Route 66 road trip will give pointers and outline the best way to experience the ‘Mother Road’ today!
1. Route 66 is not a continuous road
Route 66 has many turns and alternate routes from different periods of operation, so you do need to plan ahead on what route to take. For example, there are two ‘official’ starting points of Route 66. Jackson Blvd at Michigan Avenue (original 1926’s starting point), or Jackson Blvd at Lake Shore Drive in Chicago (since 1933). Some parts of the route is a narrow cement road, in others it is an abandoned four-lane. In one area it’s a dead end, and another is replaced by the highway. Route 66 is also only labeled in some sections, and each state has different labels and traffic signs. A map or GPS is definitely necessary for any Route 66 road trip, and having the Route 66 Navigation app is incredibly helpful.
2. You need at least 15 days
How many days do you need to spend on the road? 15 full days is the bare minimum for a Route 66 road trip experience. You may need to add one day to adjust and recover from jet lag in Chicago if you’ve had a long flight. We also recommend taking at least two days in Los Angeles to rest up after the end of the trip. If you can afford to take a longer road trip, spend at least three to four weeks on Route 66. You won’t regret it!
3. Don’t rush through it
Building on the last point, do not rush through Route 66 just for the sake of ‘doing it all’! If you try to cram a full Route 66 road trip in a week or two you will have done none of it at all. Don’t think of it as another stamp in your passport. You may brag to people by saying that you’ve ‘been there, done that’, but you would be better off just reading about it in a book. Route 66 is not just a vacation you take, it is a community and a way of life! If you only have a week, it’s best to plan a one or two states trip in places that you’re most interested in.
4. East to west or west to east?
Before moving forward with further plans, which direction do you plan to travel in? Historically, Route 66 begins in Chicago and ends at the Santa Monica Pier in Los Angeles. Most travelers follow the Mother Road as it was originally built – from east to west. However, you will also meet bikers, cars or RVs going in the opposite direction everyday. There may be some difference in airfares depending on season, but bike and car rentals are the same from either direction.
4. Best time to travel
Spring to late fall is ideal for a Route 66 road trip. You’ll be travelling across vastly different landscapes – starting in fertile Illinois and gradually passing through the prairie to the desert. Weathers can change dramatically on Route 66. Prepare for high heat and humidity, while extremely dry air in the prairie and desert. That said, September is most ideal for a Route 66 road trip. The temperature in the desert drops to 38°C, while ranging between 23°C and 32°C in other parts.
5. Don’t expect five-star accommodations
Budget travelers will be able to find something suitable almost everywhere, but those seeking luxury hotels may struggle in a few places. Wherever possible, we recommend staying at Route 66 era motels or Route 66 themed hotels, and also supporting local businesses! This doesn’t mean that you should avoid chain motels, but the thing is that although they should provide the same standard, this is often not the case. One motel may be very well-furnished, but another one in another city may have a different standard.
6. You won’t get to see everything
Sad, but true. Be ready for the fact that you won’t manage to see some attractions. Part of the charm about Route 66 is that it is such a treasure trove of beautiful places that you wouldn’t see them all even if you had a month. If you accept this, you’ll enjoy your Route 66 road trip much more. Otherwise you’ll be rushing all over the place, trying to cram as many different attractions as you can and spending such a short time at each spot that you only leave with the memory of being in a rush.
7. Be friendly!
The residents on the Mother Road are generally very welcoming of tourists, so don’t be shy to give a greeting and start a conversation! What’s rude on Route 66 is stopping at an attraction, snapping a photo from an open window and then moving on. It doesn’t take much to get out of the car and say a “hello” to the owner! Many times, they may even have interesting stories to tell that you wouldn’t know of if you didn’t get off your ride. Try to give back to the people of Route 66 as they’ve given you.