The American Dream signifies something different for everyone but one thing is true: we all crave that freedom that comes associated with it. And a road trip down the old Route 66 signifies exactly that! While it used to be more popular back in the day, and these days it seems like people value overseas vacations, there is something authentic and amazing about exploring our own beautiful country!
You do not have to travel thousands of miles away in order to get the best sceneries and experiences for your loved ones. Route 66 has kept its charm and we encourage you to consider going down it again or for the first time if you did not get to do it yet! Be it that you are revisiting or thinking of the route you are going to take for the first time, whether you already have a set in stone plan with attractions you want to visit or you plan to wing it as you go, we have gathered ten of the must-see stops that you can make along Route 66!
Before you plan to set out for your trip, make sure you read our list. Who knows? Maybe you didn’t know about these places before. Let us know if any of our gems surprised you!
Grant Park
Like many others, you may want to choose to begin your journey on Route 66 in Chicago: more specifically at the Buckingham Fountain in Grant Park, which is the city’s oldest fountain, and then head west.
You can easily find the original “Historic Route 66 Begin” sign and take a picture to immortalize your start, it is just on the southern side of Adams Street if you look towards Wabash Avenue. A lot of places tell you how to get there using the street names, but if you are not from the area you can easily find it on Google maps and on most navigation applications.
Moreover, if your route doesn’t take you back to Chicago, you can also find the “Historic Route 66 End” just a street down, at the intersection between Jackson and Michigan avenue. You may not actually end it there, but it would be a nice picture to put at the end of an album when you show your family and friends the memories you made on your trip.
Route 66 State Park
When passing through Eureka, Missouri, you have to make a stop at the Route 66 State Park visitor center. Located in the old Bridgehead Inn, which was built in 1935, it offers everything you would want when it comes to the vast history of the iconic highway.
You can take the opportunity to take a break and stretch your legs at the park, be it for historical reasons in the center, or just because you are road-weary. The park has multiple nature trails and picnic sites, so it is a great pit stop for lunch and a break.
Henry’s Rabbit Ranch
There are numerous attractions down the route that are massive and even if you do not stop by to admire them, you can definitely see them from the road. It definitely helps when the heat starts to become unbearable. However, at this stop, you will have to and will want to get out of your car, especially if you have children with you.
Henry’s Rabbit Ranch can be found in Staunton Illinois and it offers tours of their ranch where you can meet some fuzzy friends, definitely a great change of pace from the driving and an opportunity to take a break. Moreover, we doubt you can lie and say seeing some cute rabbits wouldn’t make your day better.
One thing to keep in mind is that you have to make an appointment beforehand if you want to take the tour, preferably in advance so you would not end up disappointed if you stop by spontaneously. It gets more fun as you can also see a different type of rabbit, the Volkswagen Rabbits, and you can also pick up some of their Route 66 gifts and memorabilia.
Sitgreaves Pass
Up high in the Black Mountains of Arizona, you can find the Sitgreaves Pass. A beautiful mountain pass with splendid views that will steal your breath away and it is definitely a great stop on our road trip. The road up to the summit, Oatman Road, is completely paved, so you do not have to worry about banging up your car. And, it’s also just 22 miles long, making it a breezy drive.
You can admire the road that was used centuries ago by Native Americans, miners, outlaws, Spanish explorers, and homesteaders. Upon the top of the summit, if you look to the west side you can see the remnants of the Gold road Ghost Town, standing been the current activity of the Gold Road Mine.
If you look around closely you can find the Gold road Cemetery as well and if you want to explore a bit on the north side you can see a rock stairway that will lead you to the “Shaffer Fish Bowl”: the natural spring now hosts a myriad of goldfish that were brought there by a traveler a long time ago. Just be careful not the scare them, as they seem to assimilate any shadow with birds out to get them.
The pass is an amazing place to visit while on your Route 66 journey, so if you have the time you should definitely go pay it a visit. Just be careful up the road, as even if it is paved, it does not have a lot of guard rails and even a little bit of error can end up in a tragedy.
Midpoint Cafe
You probably guessed it by the name, but the Midpoint Cafe marks the exact middle point of Route 66. The road in Adrian, Texas even went as far as having a white line on the road to have a visual representation of this middle point, together with a sign that makes note of the distance between Chicago and Los Angeles- 1,139 miles away in each direction.
You can take a picture with the sign and add it to your collection (as it completes the trio with the “begin” and “ends” signs) and then make a stop at the cafe as well. Hungry motorists have been stopping here for years for a good ol’ American burger.
What’s even cooler about the cafe is that it also served as inspiration for the cafe in the animated movie “Cars”, which was run by the character Flo. You know the atmosphere is legit when it inspires a diner in massive animated production.
Meramec Caverns
A lot of the stops on the motorway are all at ground level, be it that you have to climb up the mountain or not. Yet, there is something special in Stanton, Missouri that will definitely enchant you and make sure you will stop at their attraction.
The city is home to the Maramec Caverns, a beautiful natural underground cave, which stretches on multiple levels. The natural wonder has been opened to tourists since 1933 and the myth goes that it has been a hideout for Jesse James and his crew back in the day.
You can get a full experience by walking through the cave, but you have to be well prepared: the full tour takes about 1 hour and 20 minutes, on a well-lit path that stretches for about 1.25 miles. It is not that much to walk, but due to the nature of the caves, you have to make sure you bring a hoodie or warm jacket with you so you don’t get cold, especially if you are visiting during summer.
Old Log Cabin
Pontiac, Illinois offers everything a driver can want from a hearty breakfast in the form of the Old Log Cabin restaurant. Opened in 1926 as a roadside lunch place and gas station, the restaurant still stands up proud and serves customers from the wee hours of the morning to late at night, as it is open from 5 a.m. to 8 p.m.
It may seem like a place made for tourists, but it is actually a very loved place even by the locals, as they swear by the cheeseburgers, homemade coconut cream, and rhubarb pie. If you do not trust us, you can definitely trust the local folks, as the restaurant wouldn’t have made it this far if it was not for the local clientele.
66 Drive-In Theatre
Do you remember the golden days of drive-in theatres? All the moonlight dates to see the latest movies from the comfort of our cars. There was something exciting and special about getting to go see a movie like that, and there was the benefit of not having some stranger ruin your viewing experience because they were in a completely different vehicle. Most of these drive-in theatres have disappeared since their height in the 1950s, but Carthage made sure to keep the old tradition alive.
If you happen to pass-through Missouri and you plan on spending the night in Carthage, it would be a cool experience to relieve and maybe share with the younger members of the family who did not get to experience it. The 66 Drive-In Theatre is one of the around 325 remaining such cinemas in the United States and it’s open early April through mid-September each year.
Make sure you check their movies before going to the location!
Wigwam Village Motel #6
Going down the 66 can be a very exhausting trip, especially if you happen to be the only one driving. And even if you are not, as much as it is an amazing experience and something that we all should experience at least once in our lives, it is still a tiring vacation. That is why you should make sure you plan your journey ahead and the places where you are going to spend the nights.
If your planned stop happens to be in Arizona, you have to check out the Wigwam Village Motel #6. It is number 6, as there are five other previous iterations across the United States. The owner was charmed by the wigwam villages he’s seen in Kentucky and decided to open the motel in 1950, which now has become a part of Route 66’s history.
Despite its age, the whole location has been modernized and renovated so you do not have to worry about conditions. They do have air conditioning and cable, most probably you will not have to worry about getting internet there.
Even with the renovations, it still maintains its vintage air and aesthetic, complete with the classic display cars out front. It’s a great place to spend the night while you are passing through and you can help the family business: yes, the place has been passed down from generation to generation.
Original McDonald’s
There are a lot of original fast food places that you can hit when you are on Route 66, but one that you should definitely pay a visit to is the original McDonald’s from San Bernardino, California. Opened in 1948 close to the route, the location was partly why the chain store became so popular.
That, and because in 1954, a businessman walked inside to sell the McDonald brothers milkshake mixing machines. The rest made franchising history. And if you find yourself around, it would be a really nice pit stop, seeing where a part of history was made. If not for that, then we all know that they have the best french fries out of all the fast-food chains.
If the Route 66 drive sounds a bit daunting to you (both because of budget and distance), you can always check out these budget-friendly getaways throughout the states!
13 thoughts on “10 Amazing Gems Along Route 66 You Will Regret Missing”
I enjoyed all this history. Thank You
Should have been in order
Silvana has written an interesting article however the list of site ms to see is in a jumbled order. It would be more useful to a traveler to list these sites in trip order especially since you actually “start” in Grant Park. Thanks
I agrre with Rolfe I’m planing a trip next year from Chicago to Santa Monica on rt 66
As I kept going from place on Route 66, I was certain Chloride, Arizona would surely be noted. It’s okey though because last I heard and saw, Chloride residents were perfectly satisfied with their quiet surroundings. My Grandma married William Epperson, a cowboy and well respected Deputy Sheriff in Cloride. I spent several summers there and even attended class in the school house. My Aunt served breakfast at the local bar before the work day began. Every day a donkey came through the swinging doors, up to the counter for his morning ritual, a stack of pancakes.
So here I am, in my glory, reminiscing and thanking my wonderful Parents who wanted me to see the other side of glamour and glitz of the big cities in California where I was born 84 years ago.
What about Oatman, Arizona? It’s a little town with “old west” charm right along route 66.
Hi Marilyn. Exactly my thoughts. I have been to Oatman many, many times as it is not too far from where I live, and I always find something fun, and historical about it. It’s a great place to visit, and there is quite a lot of history behind it. I still go there from time to time, and I never tire of it. It should have definitely been one of the stops on this list.
If you want to live to make the rest of the trip, skip the ‘original rt 66’ sign in Chicago. Besides, it’s not an original sign anyhow, it’s a sign from AFTER 66 became ‘history’.
Yes I drove that road when it was the main road. Stationed at the Marine base at Barstow Ca. Drove it every day and went to San Bernardino Ca to all the way to Texas on my way home prior to going over seas. Also drove it to get to the cut off to Big Bear in the mountains. Maybe put 2509 to 3000 miles on that road in the mid 1957 to mid 1958 .
In my mid-70’s now, my FIRST knowledge/experience with the Mother Road, Route 66, was in around April 1965, in Amarillo, Texas.
I was in USAF tech school there at Amarillo AFB, closed long ago…sometime in 1968, while I was later stationed in S.E. Asia.
Rt. 66 was/is Main Street for the town/city of Amarillo, on which the locals held their Friday night hot/street cruises, which were absolutely FABULOUS…again back in 1965.
Of course, none of us GI’s could afford a car there, but the cruises were fun to watch, and we felt like ‘temporary civilians’.
MANY years later, my bride and I had our family in William, Arizona, during our ‘Western Tour’, where Rt. 66 was again, the main street.
Top of MY ‘Bucket List?…drive, dine, and hotel/motel on the ENTIRE length of the Mother Road, Rt. 66, from Chicago the the Santa Monica Pier, California, in a 1964 or 1965 Pontiac GTO, of COURSE.
Honestly…(and unfortunately), at my age, and limited resources this day and age…I doubt I’ll make it.
By the way….job well done, Sylvana
I LOVE IT !!!!
I’ve lived in Oklahoma all my life, and I’ve lived close to Highway 66.
You missed the Grand Canyon Caverns, in Arizona. Largest dry cavern in North America. Neat place.