As U.S. Route 66 celebrates it 100th anniversary in 2026 (along with several other numbered U.S. routes in the nation), it gives tourists who haven’t had the chance to experience the old-time Chicago-to-Los Angeles connection a reason to. Pontiac is one of the Illinois stops, and stop one will.

For a small town just north of 10,000 residents, Pontiac offers several tourist options that has helped boost the city’s economy. Route 66 plays a large role in it. From 1926 to 1977, Route 66 was a major road through the nation. As documented in the 1930 census, Chicago was the second-largest city in the country, St. Louis once was in the top 10, and Los Angeles was fifth. The Chicago-to-St. Louis stretch was heavily traveled, and towns along that path prospered – including Pontiac. Outside of the Chicago Metro area and St. Louis’ Metro-East, Pontiac is the fifth-largest city between those, behind Springfield, Bloomington, Normal and Lincoln.

Tourism is strong in Pontiac, and I experienced that as a teenager. I went on a three-leg trip with my grandparents along Route 66 as a kid. We only made one stop in Pontiac, which I will mention momentarily, but as I got older, I discovered a renewed need to go back. My appreciation for travel and tourism evolved into adulthood. So why not go back?

I charted six places in Pontiac to visit some day. As of this writing, I have visited four of them, with two more left for another trip. Perhaps that is for the best, as new things may appear at the places I did see. If you’re just passing through town, however, to get the most out of your Pontiac experience, you’ll need to stay at a hotel and whip through each of these sites pretty quick. If you’re someone like my grandparents, and like to look at every single thing in a museum, plan for two nights.

I made trips to Pontiac in February and July. I visited the Illinois Route 66 Hall of Fame, the Oakland-Pontiac Auto Museum, the Old Log Cabin restaurant and Wally’s truck stop.

***Click here for my Pontiac photo album for pictures*** (coming soon!)

Illinois Route 66 Hall of Fame

Visited: Feb. 27, 2026

This is my second trip to this museum, nearly 25 years after my first one as a high schooler. Since then, several more inductees – and their unique stories – have been enshrined in the Illinois Route 66 Hall of Fame. These people have met people from all walks of life who have traveled down that highway, and it shapes their own lives. Their stories are told in this museum.

The Illinois Route 66 Hall of Fame is located in the vintage-1900 City Hall building, where at one time it also was home to the police and fire departments. As mentioned, the Chicago-to-St. Louis stretch of the highway had several travelers, and thus several businesses and stops along the way. That itself makes the Illinois-themed highway museum unique among other state stretches (and far better than the 13 miles it travels in Kansas, for example).

Exhibits appear both in a hallway and a large room that originally housed the fire trucks. Temporary exhibits related or unrelated to the Route 66 experience also are available on the building’s second flood, and this one was an exhibit about life in the 1940s.

On most days (including this day I visited), longtime docent Rose was behind the counter, and she can tell you just about everything you need to know about this Illinois stretch. [In fact, she also informed me about the eastern “terminus” of Route 66 “moving to” Navy Pier – my thoughts on that linked here.] Visitors wind through a maze of glass cases with information about each inductee (which can be a person, place or thing). Artifacts from their lives and/or businesses are preserved in hopes to elicit memories of decades past. One of the inductees, Bob Waldmire was a Springfield-born artist, illustrator, preservationist and one of the most colorful personalities associated with Route 66.

Waldmeier traveled the Mother Road in his hand-painted Volkswagen van, which served as both a vehicle and a mobile art studio. Waldmire filled it with his artwork, maps and Route 66 imagery; it documented the road and helping promote its preservation. His van later became part of the museum’s collection and famously inspired Fillmore, the hippie Volkswagen bus character in Pixar’s Cars. The side door is open, and visitors can peek inside Waldmeier’s collection:

Here are three more of some of the interesting inductees, and their stories:

Bill Shea of Springfield turned a lifetime on Route 66 into a living piece of roadside history. After operating Texaco and Marathon stations, Shea transformed his Route 66 station into a museum packed with gas-station memorabilia and artifacts. He greeted thousands of travelers from around the world and was inducted into the Illinois Route 66 Hall of Fame in 1993. His former station has since been revived, and Shea’s name and legacy remains connected to the Mother Road. Joy Henderson represents the everyday business owners who gave Route 66 its character. With her husband, Archie Wilbur, she operated two small roadside businesses in the early 1960s: Archie’s Standard Service in Pontiac and the Hill Top in Cayuga. Tom Teague helped turn appreciation for Route 66 into an organized preservation movement. A Springfield resident and journalist, Teague founded the Route 66 Association of Illinois, became its first president and established the association’s publication: “The 66 News.” He also conceived the Illinois Route 66 Hall of Fame itself. 

Illinois Route 66 Museum
110 W. Howard St.
Visitpontiac.org/experience/museums-exhibits/route-66-museum
Hours: 9 a.m. to 5 p.m. daily from April to October, 10 a.m. to 4 p.m. daily from November to March

[As I was writing this, I happened to realize that I have LOST most of my photos from this stop due to a misplaced memory card. Damn! Looks like I’ll be headed back. I was going to anyway. The two above are from my cell phone.]

Pontiac-Oakland Auto Museum

Visited: July 14, 2026

What’s a city named Pontiac without some sort of reference to the automobile manufacturer? While most people know of the word when it comes to cars – and stylish ones, too – the name originates from the Odawa war chief from the Midwest who feuded with the British in the mid-1700s. (Odawa was later Anglicized to the more familiar spelling of “Ottawa”). In the heyday of Route 66, Pontiac’s logo was that of a chief’s head; now it’s stylized in the shape of the more familiar red isosceles triangle.

The Pontiac Trail was the name of the early motor route before Route 66, and I have written about this in a separate entry.

The Oakland brand of General Motors cars eventually evolved into the Pontiac brand. Oakland was around from 1908 to 1931. The Pontiac name had also been used for other means of transportation, and a sled from the 1890s is at the museum which bears the name; it was manufactured by a company named Pontiac out of Virginia. The modern Pontiac also manufactured other products, such as a refrigerator which is on display.

Aside from sleds and fridges, it’s the cars people come see at the Pontiac-Oakland Auto Museum. Its rotating collection offers more than a parade of muscle cars. Among the vehicles in the current display (as of my visit) are a 1970 Firebird Formula 400, a 1964 LeMans convertible, a diminutive 1991 Firefly convertible, a 1978 Phoenix hatchback and a 1989 6000 STE. Those five cars trace Pontiac’s evolution from the performance-minded 1960s and ’70s into the smaller, more technology-focused vehicles of its later years. There is something here for the muscle-car enthusiast, but also plenty for anyone interested in the less-remembered corners of Pontiac history. 

One of the rooms is a vintage garage setting with oil cans and other parts and car products inside. A library also is available for those who have a serious interest in research. One of the exhibits had an autographed hat from Arnie “The Farmer” Beswick, a drag racing legend known for his association with Pontiacs. (Beswick is from Morrison, and I wrote a story about him in early 2025).

Before visitors go through the front door, there’s already something waiting for them. Through the front windows is a wheel cover quiz: Pick up a sheet inside and match which one to what.

Pontiac-Oakland Auto Museum
205 N Mill St.
Pontiacoaklandmuseum.org
Hours: 9 a.m. to 5 p.m. daily

The Old Log Cabin restaurant

Visited: Feb. 27, 2026

Route 66 had several alignments through and around Pontiac. It entered town from the north directly from the edge of town to downtown when the route was established in 1926. Then it was rerouted around what was then the west end of town in 1930. It was rerouted even further west when the road expanded into a four-lane divided highway during World War II. Interstate 55 finally supplanted the route even further west in the 1960s. Brown signs give travelers an idea on which alignment was which.

The rerouting of the highway is part of the story of the Old Log Cabin restaurant on the north edge of town. During the first re-routing, the building was lifted up, turned 90 degrees and set down when the road shifted directions. The front door used to face south toward the original road, now it faces north toward the rest of the Route 66 alignments.

The restaurant is essentially a timewarp back to Route 66’s heyday, even down to the table chairs. Not much has been modernized since, and that’s okay, given a trip on the road is mostly about going back in time anyway for travelers. A packet with the place’s history is available for curious readers, as is a guestbook to sign.

Old Log Cabin
18700 Old Route 66
Hours: 7 a.m. to 2 p.m. Monday through Saturday

Wally’s

Visited: Feb. 26, 2026

National Lampoon’s Vacation gave those in the 80s a new reason to go road tripping, with a variety of wacky adventures and situations. More than 40 years later, the “Vacation” nostalgia hasn’t faded. In fact, it’s become a business centered on travel and the “great American road trip.”

Places like Love’s and Buc-ees have made truck stops grow gigantic in recent years, and Wally’s is like that, too. The business has locations in Pontiac, Fenton (MO) and Whitehead (IN). The Pontiac and Fenton locations are along the path where the Griswold’s would have traveled from their Chicago home out west to Wally World in the movie. Fenton is outside of St. Louis. Wally’s is branded in orange and white lettering, and a replica Wagon Queen Family Truckster sits outside the Pontiac location – not in an olive green color, but the brand’s usual orange (the wood motif paneling is still there).

Visitors are greeted to the truck stop by passing a Vegas-like sign, lit in colors at night, which reads “Wally’s: Home of the Great American Road Trip.” There are 76 fueling stations where customers can use their cards at the pump or prepay inside. The inside looks like an airport terminal. There’s a manned deli station for fresh beef jerky, and another for fresh popcorn. An entire wall of packaged beef jerky is available. Several everyday gifts and sundries are stamped with the Wally’s name on it. If something exists, it’s likely there with the Wally’s name on it.

Just be careful not to get too overly hooked on finding things you “need,” or else you’ll be kicking yourself come checkout. Did I “need” a plastic coin holder? You know, the ones with the slit through the middle, and you squeeze it to open it? No, but it became my Wally’s souvenir. (And I still put coins in it!)

That being said, there are different brands of grocery-like stuff, each with their own unique tastes or style. Perhaps something will become your new favorite.

Wally’s
1 Holiday Road (like the song in the movie)
https://www.wallys.com
Open 24 hours

More Pontiac

Pontiac is a tourist destination in many ways. Obviously, Route 66 is a big part of that. For a town of 10,000, it offers a lot to see, enrich and offer compared to other towns its size. It’s not often when I go through a town of Pontiac’s size and need to tell myself, “I need more than one day to take in the experience.” That’s meant to be a compliment.

There are two places that time constraints failed to make me visit, but that just means going back for more.

They are:

• The Livingston County War Museum: 321 N. Main Street. It is inside the old City Hall building where the Illinois Route 66 Hall of Fame is. It is a hands-on, community museum dedicated to preserving and sharing the military history of central Illinois through the lens of local service members. Founded by veterans and staffed largely by those who served, it focuses less on sweeping national narratives and more on the personal stories, artifacts and sacrifices tied directly to Livingston County. Exhibits span from World War I to modern conflicts in Iraq and Afghanistan, featuring uniforms, weapons, letters and memorabilia that bring each era into human focus. Visitors move chronologically through America’s wars while encountering the individual faces and experiences behind them, often shared firsthand by volunteers. The museum’s mission honors service and educate future generations, and it creates an experience that feels intimate, reflective and deeply connected to the community it represents.

• Museum of The Gilding Arts: 217 N. Mill Street. This is a compact, highly specialized museum dedicated to the centuries-old craft of gilding – an application of delicate gold or silver leaf to surfaces for decoration. Operated by the Society of Gilders, the museum traces the technique from ancient civilizations to modern uses in art, architecture, signage and design. The process from how gold leaf is produced to the tools and careful methods used to apply it are explained through exhibits. There is a recreated 19th-century gold-beating workshop that offers a glimpse into the labor-intensive origins of the craft. It’s a practice many people see but rarely understand. Though small in size, the museum is one of the only institutions in the country devoted entirely to the niche decorative art of gilding.

Car enthusiasts on this stretch can also hit both the Oakland-Pontiac Auto Museum in town and the Crazy 80s Car Museum in Dwight – about 20 miles northeast – on a Tuesday, Thursday or Saturday.

I’ll update this post when I make it back to town.

***Click here for my Pontiac photo album for pictures*** (coming soon!)