pontiac trail sign

The Pontiac Trail – A Day Trip on Route 66

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The Pontiac Trail – A Day Trip on Route 66

Are you looking for an adventure filled with nostalgia, Midwest charm, and some time behind the wheel? If so, the section of old Route 66 between Chicago, Illinois and St. Louis, Missouri is filled with plenty of adventure to get you “off the beaten path” and back to what made the American road trip famous. Jump on the Pontiac Trail and take a day trip on Route 66.

Pontiac Trail

Affectionately called The Pontiac Trail, this route was the original route traveled between Chicago, Illinois and St. Louis, Missouri. As we know, this route later became Route 66, “The Mother Road”. Pontiac_Trail_sign

Research will show that there are/were different sections of Route 66 in use at different times in history. The oldest sections of Route 66 follow the Pontiac Trail in what was designated as Illinois Route 4, which is the route we decided to explore on our Pontiac Trail day trip along old Route 66.

Having traveled most of the eastern sections of old Route 66 from Bloomington to Chicago at various times, we decided to explore the western section of the Pontiac Trail. Starting in Chatham, Illinois and working our way down to Edwardsville, Illinois.

Read about our day in Pontiac, Illinois HERE.

This particular section took us about three hours to drive with some stops for some local adventure and sightseeing.

Below are some highlights of some sights along this section of Route 66. This is just a sample of some sights you’ll encounter along this route, we don’t want to ruin it for you by giving away too much.

Here is a good website as a reference for the different routes that can be taken along Route 66 in various states – a great reference with good directions and tips. Click HERE


Springfield, Illinois was not on our itinerary for this trip. Springfield, onetime home to President Abraham Lincoln and state capitol, really needs its own post and much more time to explore. So, we bypassed Springfield on this trip.



First stop….

Chatham, Illinois

The Old Chatham Bridge, pictured above, was an early route that was in use for a short time. By 1930, better and straighter roads bypassed most of Chatham.

The old bridge is obviously no longer in use, except for what appears to be support for a water line supplied by a nearby pump station.

The bridge was hard to locate due to poor GPS coordinates and the fact that the Old Chatham Road is mostly closed to traffic yet still marked. Not a worthy destination for sightseeing, but I had to start somewhere.

On to…..

Auburn, Illinois

A lovely town with some of that Midwest charm we talked about above.

Seen below is the double-decker gazebo that sits in the middle of the town square. Oddly enough, you can’t get to the second level of the gazebo. So, we were left wondering what the purpose of a double-decker gazebo would be if you can’t get to the upper level.

There was no information about the origins of this gazebo that we could find, however, it is still a well preserved and lovely destination to stroll around to take in a lovely day.


Below is the lovely Commercial Hotel located on the East side of the Auburn square. An interesting story found in research was that the Hotel had caught fire in about 1910 and was destroyed. There is not much other information available, however, it was obviously rebuilt and is as it is pictured here.

The Commercial Hotel

A must-see near Auburn – The Route 66 Brick Road

Bricks laid over the original concrete in this section of Route 66. Only about 1.5 miles in length, this is a must-see for the Route 66 road-tripper.

Just enter Snell Road, Auburn, Illinois into your GPS and you’ll drive right to the brick road. Definitely a photo opportunity as well – very cool place.

Next stop…

Virden, Illinois


Pictured above is the History of Virden mural. The mural is the attraction we were looking for and appears that the mural has changed quite a bit over the years – repainted and redesigned with varying highlights.

An interesting fact about Virden – A dispute between mining laborers and the Chicago – Virden Coal Company in 1898 in which the company hired “non-union” laborers when original miners went on strike led to a gunfight. 13 people would be killed in this short battle.

On to….

Girard, Illinois

A must stop in Girard is Doc’s Soda Fountain on the square.

A well-maintained example of a period Soda Fountain, Doc’s is a must-do attraction when traveling through Girard. You can sample a soda poured directly from the original fountains, surrounded by some beautiful hand-made and carved wood that would have been in the building during the time of Route 66 heyday.

I opted for a hand-dipped Vanilla milkshake, which was pretty tasty.

Doc’s Soda Fountain

Since the soda fountain was once a drug store, the owners have assembled a collection of antique items that would have been in the store during the times.

We would love to have this old Rolltop desk, but I’m sure they aren’t interested in selling.

Don’t forget to sign the Guestbook – I did and that’s me on the last line. Just a few lines up were some guests from England.


There are a few other sights located in Girard, however, we were on a tight schedule and just moved on.

West to Nilwood…..

Nilwood, Illinois

Nilwood, Illinois is a pretty small town and there isn’t really much to see. However, a fun item just south of Nilwood is the Turkey Tracks of Route 66.

During the 1920s as the concrete was being poured for what would become Route 66, a turkey wandered onto the fresh concrete and left its mark. Still there today and is marked well with a sign and outlined in a white border.

This stretch of what is now Donaldson Road is one of the best examples of concrete road that would have been Route 66 during the period when used from 1926-1930.

Pretty incredible that this road is nearly 100 years old now. Cracked with grass growing in between the cracks, this stretch of road is not in too bad of shape. Sadly, this is the best example we saw of the original road.

turkey tracks photo

Directions – Approximately two miles West of Nilwood, turn South onto Donaldson Road. The turkey tracks are about one and a half miles down the road. Well marked so you can’t miss it. GPS may not work.

Next stop …..

Carlinville, Illinois

Carlinville, Illinois is the county seat of Macoupin County.

With a fabulously well-kept downtown area, Carlinville is definitely on our list to return to when we have additional time to visit.

The town square offers period architecture that has been well preserved, great food options, some limited shopping, and a fabulous destination to just walk and enjoy a wonderful Midwest town.

Macoupin County Courthouse

An interesting story about the courthouse. Construction began in about 1870 with an estimated cost of $50,000. Construction was stopped when costs ballooned to over $1 million. Parts of the courthouse were never finished.

At the time the courthouse was built, it was the second largest courthouse in the United States.

On to …..

Gillespie, Illinois

Michelle’s Pharmacy in Gillespie is home to a lovely depiction of the Route 66 heritage and period.

The depiction of the Civil War soldier was once a large statue in the town that was located near the drug store. It is no longer located there and there was no information pertaining to its whereabouts.

I just love murals.


Next to last stop ….

Edwardsville, Illinois

Edwardsville, Illinois is a bustling, busy Northeast suburb of St. Louis, Missouri.

Home to the University of Southern Illinois at Edwardsville, the town has seen rapid growth over the years and is largely due to the university.

Still embracing its historical roots, Edwardsville’s downtown area certainly does not look much like it would have during the heyday of Route 66. However, many of the important buildings, homes, and other sites still remain.

One such site is the Wildey Theater.

Constructed in approximately 1909, the theater was conceived by the International Order of Oddfellows. The theater has seen big-name entertainers such as Ginger Rogers and W.C. Fields during its years in operation.

The last film shown before the theater was closed from full-time operation was “The Big Chill” in 1984. Some 400 patrons attended including media.

The theater was purchased by the city of Edwardsville in 1999 and is still operating to this day.

Here is a link to the theater EVENTS – Who knows, maybe you’ll be passing through town and want to take in a show.

Wildey Theater

A photo of Wildey Theater wouldn’t be complete without a shot of its next-door neighbor, Herby The Hereford.

Herby was erected atop the butcher shop that resided next to the Wildey Theater during the late 1940s. Herby is still there today but his red fur is looking pretty faded.


Edwardsville, Illinois is pretty much where our adventure ends for this segment of Route 66.

Our last stop of the day – Fire-N-Smoke BBQ. Just a quick ten-minute drive from downtown Edwardsville, you’ll find some of the best BBQ between Chicago and St. Louis.

fire and smoke logo

HERE is a link to our review of Fire-N-Smoke from a previous visit – We stopped this time as well and I highly recommend it after a long day of adventuring.

Travel Tips

  • Give yourself plenty of time for driving. You won’t be doing 65-70 on these roads – this is old school road tripping.
  • Do some online research of sights that interest you and just plan to hit those. You likely won’t have time to see everything – some things won’t be worth seeing.
  • Visit one or two sections of the “old” road for nostalgic purposes but stay on the main highways for the most part. Most of the original road is in pretty bad shape or has been cut up into smaller side streets. Route 66 signs with directional arrows may take you onto the old road only to put you back on Route 4 in half a mile or maybe just a few hundred feet. It just isn’t worth the constant turns and stops.
  • Buy a map or reference book such as this one I recommend. GPS may or may not work in some locations depending on your cell service and you may find yourself needing some old fashion paper maps or guides. There are also travel tips included in this guide – very handy.

Buy this Guide Book from Amazon HERE

  • Some destinations or sites along the route may still show on searches, however, are closed or moved. We found this to be true at least twice on our trip. Good research will help with this.

So, there you have it folks, The Pontiac Trail – A Daytrip On Route 66. At least the western section of Illinois’ Route 66.

Now that we have your interest sparked, get out there and see what the old “Mother Road” has to offer – there still is really a lot to see on this great American road.

route 66 pinterest


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  1. Such an incredible day trip! I’ve lived in Wisconsin my entire life and still have yet to explore any part of Route 66 in Illinois. Thanks for sharing this beautiful section of the road and the gems to stop and see along the way!

    1. Sure thing – You’re closest to the Chicago section and that’s just as cool. You really should plan to do that sometime – very historic and fun. Thanks for stopping by

  2. What a great way to take a ride on Route 66 for the day. I have never visited these towns and the all look cute. Will add to our fall weekend list.

    1. Excellent – was a really fun afternoon. I do highly recommend if you’re traveling through the area. Or, any part of Rt 66 really. So much history. Thanks for stopping by.

    1. That’s great Jim. I live near Peoria and travel around that area – mostly in the Pontiac area. This was my first time heading West on Rt4 or 66 as it would have been. It’s on my bucket list to drive the entire route someday – probably in sections similar to this trip. Thanks for stopping by.

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