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Illinois Route 66 The First Hundred Miles

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Embarking on Illinois Route 66 The First Hundred Miles is a journey like no other.

This iconic stretch of highway, fondly known as the “Mother Road”, holds an allure that’s hard to resist.

The enchantment of this famed “Mother Road” is not merely found in its picturesque views, but also in the wealth of stories and traditions that it holds. It’s where nostalgia meets adventure.

Taking you through quaint towns, vintage diners, and quirky attractions – Illinois Route 66 The First Hundred Miles promises an unforgettable road trip experience.

betsy route 66 sign
Photo by Betsy Wuebker

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Embarking on Illinois Route 66 The First Hundred Miles

The charm of the globally-renowned Route 66 is undeniable. America’s “Mother Road” stretches across beautiful rolling country hills in central Illinois, offering a journey like no other.

historic illinois route 66
Photo by Betsy Wuebker

This isn’t just a straightforward excursion; it’s an adventure that encapsulates the feeling of independence and discovery. Historically significant sites along this route are recognized by the National Register of Historic Places – each one telling tales from different eras.

A Journey Back In Time: Chicago’s Legendary Magnificent Mile

Your adventure begins not amidst open fields but within vibrant city life – right at Grant Park downtown Chicago where Lake Michigan paints a picturesque backdrop before you head southwest towards Joliet.

You’ll pass iconic landmarks including Willis Tower (formerly Sears Tower) or even partake in cruising down part of Chicago’s legendary Magnificent Mile – juxtaposing historic architecture with modern skyscrapers side by side for your viewing pleasure.

chicago skyline at night
Image by 350543 from Pixabay

Capturing Memories: Snapshots Along Illinois’ Route 66

An integral part of any trip are those captured moments frozen in time. And there are plenty throughout these hundred miles worth hitting the brakes for. Whether standing next to oversized statues found scattered across the landscape or capturing vintage neon signs lighting up small-town main streets after dusk – every photo serves as tangible proof marking your unique experience on this legendary road.

In fact, if luck favors you might spot classic cars parked outside diners or motels adding another layer to your nostalgic ride back through time.

Planning Your Journey with The First Hundred Miles

The charm of Illinois’ Route 66 is not just about the open road. It’s also about the unique attractions, mouth-watering eateries and lively events that dot this historic highway. This is where Heritage Corridor Destinations, a comprehensive tourism brand dedicated to promoting these distinctive features along Illinois’ Route 66, comes into play.

Heritage Corridor Destinations is an invaluable resource for anyone planning their journey on this stretch of road, offering detailed information from Chicago’s legendary Magnificent Mile to the beautiful rolling country hills further down south.

Note: I was the guest of Heritage Corridor Destinations on a Sponsored Familiarization Trip in conjunction with TBEX. Our itinerary included curated stops on Route 66 south of Chicago in the communities of Burr Ridge, Joliet, Wilmington, Braidwood, Dwight & Pontiac.

Subscribing to Heritage Corridor Newsletter

To keep your finger on pulse of everything happening along Illinois’ Route 66 experience, subscribing to the Heritage Corridor newsletter can be a game changer. Delivered straight into your inbox at weekly intervals throughout the year; it provides timely reminders about upcoming events such as festivals or car shows while highlighting newly opened restaurants worth checking out during your trip.

No matter how adventurous you are feeling when embarking upon a journey across central Illinois via Route 66 – having some guidance can come in handy especially if time constraints factor into travel days. Hence, planning your visit with resources from Heritage Corridor is essential. Highlights include key points of interest such as historical sites, noteworthy landmarks, delicious dining destinations, and others thus ensuring travelers won’t miss anything important while cruising down Mother Road.

Click to Request a Free Visitor Guide

Besides providing interactive map assistance they also offer categories tailored according different interests whether someone prefers focusing heritage aspects, wanting to explore culinary delights, or appreciates outdoor activities.

Last but certainly not least, their social media platforms on Facebook and Instagram serve as additional sources of inspiration, offering sneak peeks at what to expect visually through captivating images shared by team members and fellow travelers alike.

Key Takeaway: 



Illinois’ Route 66 is more than just a highway; it’s an adventure filled with unique attractions, delectable eateries, and lively events. Heritage Corridor Destinations offers invaluable resources for planning your journey, including detailed information from Chicago to the rolling country hills down south. Subscribe to their newsletter for updates on upcoming events and behind-the-scenes content.

Iconic Stops on Illinois’ Route 66

The journey along the globally-renowned Route 66 is marked by a plethora of noteworthy attractions. Each stop, like turning a page in an American history book, offers its unique slice of culture and heritage.

Play Your Way Down Route 66 at Harvester Park

Harvester Park is a great stop for kids of all ages. Designed to emulate a road trip down the length of Route 66, this theme park has a colorful, interactive array of structures and areas designed for active play. The Route’s attractions and geography are detailed in visual learning stations that provide an interesting overview for grown-ups and older kids while the little ones run off their pent-up energy.

harvester park
Photo by Betsy Wuebker

Nostalgia at Polk-a-Dot Drive-Inn and Bob & Ringo’s Tavern

Experience firsthand the charm of classic Route 66 restaurant features at places such as Polk-a-Dot Drive-Inn and Bob & Ringo’s Tavern. Transport yourself back to simpler times with kitschy decor and ambiance.

polk a dot drive inn sign
Photo by Betsy Wuebker
superman polk a dot drive inn
Photo by Betsy Wuebker
elvis polk a dot drive inn
Photo by Betsy Wuebker

Providing more than just food, these eateries offer nostalgia wrapped up in every bite.

bob and ringos tavern
Photo by Betsy Wuebker
bob and ringo's rib plate
Rib’s at Bob and Ringo’s. Photo by Betsy Wuebker

Experience the Historic Legacy of Old Joliet Prison

joliet prison
Photo by Betsy Wuebker
joliet prison wall
Photo by Betsy Wuebker

Check out the iconic appearance – remember The Blues Brothers movie scene? – of the Old Joliet Prison in an outdoor walking tour which covers the prison’s general history since it opened in 1858.

betsy with jake and elwood
Photo by Betsy Wuebker
joliet prison yard
Photo by Betsy Wuebker
joliet prison facade
Photo by Betsy Wuebker

Currently only partially restored, the prison’s eight-acre campus is comprised of multiple buildings which have architectural and historical significance. The site’s condition is varied, so visitors should be prepared with sturdy footwear.

joliet prison corridor
Photo by Betsy Wuebker

A Glimpse into History at Joliet Area Historical Museum

To understand central Illinois better one must immerse themselves in local history which can easily be done by visiting the Joliet Area Historical Museum.

great migration exhibit
Great Migration Display. Photo by Betsy Wuebker
pontiac rte 66 mural
Route 66 Mural in Pontiac. Photo by Betsy Wuebker
Pontiac Forefathers
Pontiac Forefathers. Photo by Betsy Wuebker

Check Out Music History at the Illinois Rock & Roll Museum on Route 66

We were thrilled to be treated to an insider’s look at the brand-new Illinois Rock & Roll Museum and learn about the rich musical legacy of Illinois rock bands and other performers. Our private tour was led by founder Ron Romero, who appears to have forgotten more than I ever knew about the Illinois music scene.

IL Rock Roll Museum

Illinois has a rich history of rock and roll legends. This graphic at the museum celebrates a variety of famous names.

Chicago Music
Photo by Betsy Wuebker

Striking a Pose with Gemini Giant

No trip down Route 66 would be complete without stopping for photos alongside some of its most famous roadside giants. One standout attraction is undoubtedly Gemini Giant located near Wilmington. This towering figure represents another quirky aspect synonymous with traveling along this hundred miles site.

Gemini giant depicts a spaceman holding a silver rocket ship – reflecting America’s fascination during Space Age era when he was erected back mid-60s . Standing tall against a verdant backdrop , he certainly makes quite impression providing the perfect photo op opportunity for travelers looking to capture the essence of their memorable journey along the historic Mother Road.

gemini giant route 66 the first hundred miles
Photo by Betsy Wuebker

Note:You may find similar experiences further ahead between Pontiac and Edwardsville that are equally captivating.

Unveiling a Blues Brothers Connection at Joliet Diner

Joliet Diner isn’t just another pit-stop along this hundred miles site – it holds significance in pop culture history thanks to “The Blues Brothers”. Fans can relive cinematic moments right where they happened while enjoying delicious dining destinations.

joliet diner
Photo by Betsy Wuebker

In addition, visitors get an opportunity for immersion into popular culture phenomenon linked directly with central Illinois’ past – making each bite count even more.

joliet diner interior
Photo by Betsy Wuebker

The diner’s vintage charm paired with classic route 66 restaurant features makes your meal there unforgettable.

Capturing Timeless Moments at Rialto Theater Joliet

Your first hundred miles wouldn’t be complete without stopping by downtown Joliet’s crown jewel – Rialto Theater known fondly as the ‘Jewel of the Midwest’. Its grandeur is architecturally echoed with details dating back almost nine decades since May, 1926 when doors were opened for public performances .

rialto theater
Photo by Betsy Wuebker

The Rialto Theater provides a perfect backdrop of ornate carvings & crystal chandeliers that add timeless elegance beyond words. If you’re lucky enough, you might catch a live performance or movie screening. So why wait? Plan ahead.

Automobile Nostalgia at Ambler-Becker Vintage Gas Station and Pontiac-Oakland Museum

If you’re a car buff, two stops along the First Hundred Miles of Route 66 will be a must. First up, the Ambler Becker Texaco Gas Station in Dwight. This vintage jewel is authentic down to the two old-timers shooting the breeze in front of the garage door.

ambler becker texaco station
Photo by Betsy Wuebker

The station is tidy and attractive with a patriotic feel.

ambler becker texaco station route 66
Photo by Betsy Wuebker
ambler becker texaco
Photo by Betsy Wuebker

Pontiac-Oakland Museum is another must-see for car buffs, with an extensive collection of Pontiac and Oakland cars and memorabilia. The display floor boasts an impressive number of autos in pristine condition.

pontiac oakland auto museum
Photo by Betsy Wuebker
pontiac oakland museum
Photo by Betsy Wuebker

Other Museums to Visit in Pontiac

Route 66 themed artifacts form the backdrop to personal histories of those who contributed to establish the highway as a major journey westward in the Route 66 Hall of Fame Museum. Bob Waldmire’s Road Yacht Mobile Home is a must-see in the parking lot here, just as when he lived in it.

bob waldmire bus

The Livingston County War Museum and Education Center honors local service members with exhibits of uniforms and personal items dating from WWI to the current day. Military veterans are on staff to bring history to life.

The Pontiac Museum Complex showcases history and photo exhibits, music of the Civil War, and life on the famous Titanic. Other points of interest in Pontiac include the Museum of Gilding Arts and several historic homes.

Where to Stay Along Route 66 The First Hundred Miles

Our group stayed at the Wingate by Wyndham Joliet. Rooms have refrigerator, microwave, and the rate includes breakfast and express check out. The second night of our trip, we stayed at the Best Western Pontiac Inn. Both places had indoor pools and onsite exercise facilities.

An Immersive Adventure: Route 66 The First Hundred Miles

Embarking on Illinois Route 66 The First Hundred Miles is a journey steeped in history and charm.

The First Hundred Miles, a comprehensive tourism brand, provides all the resources you need to plan your odyssey.

From iconic stops like Polk-a-Dot Drive-In to historic sites such as Ambler/Becker Station, every mile offers an unforgettable experience.

You’ll immerse yourself in local history at museums and capture timeless moments against architectural grandeur.

Your adventure doesn’t have to end after the first hundred miles – extend it with more photo-ops between Pontiac and Edwardsville.

If you’re ready for an epic road trip filled with vintage diners, quirky attractions, and slices of American heritage along one of the world’s most famous highways…then start planning now!

Customize this remarkable journey by using the tips, information, and inspiration included here on attractions that will make your travel bucket list even more exciting. Start exploring today!

Tips for Trip Success

Book Your Flight
Find an inexpensive flight by using Kayak, a favorite of ours because it regularly returns less expensive flight options from a variety of airlines.

Book Your Hotel or Special Accommodation
We are big fans of We like their review system and photos. If we want to see more reviews and additional booking options, we go to Expedia.

You Need Travel Insurance!
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Judy McP

Thursday 17th of August 2023

Well done! Beautiful photos. You've brought to life a route I've been down many times and just considered "fly over" country. So nice to see a domestic car trip given the exotic get-away treatment. Wonderful piece.

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