Itinerary: Two Days Along The First Hundred Miles of Route 66
The Mother Road. America's Main Street. Route 66. The road that symbolizes freedom and the days of cruising from Chicago to Los Angeles, stopping at mom and pop diners, roadside attractions, and locally-owned shops of every variety. Your journey begins with two days along The First Hundred Miles.
Day One: Exploring Lemont, Lockport & Joliet
Begin the day with stops in Lemont and Lockport, twp Route 66 communities with charming downtowns and rich history.
Then, head to the Joliet Area Historical Museum to learn about the historical Route 66 city you'll be exploring during the first leg of your trip. Here are some recommendations on what to see, eat, and explore during your time in Lemont, Lockport, and Joliet.
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Lemont, IL
After leaving Chicago, take a break to stretch your legs and refuel in the charming town of Lemont. Stroll the historic downtown and grab a bite to eat at one of many locally-owned restaurants. Then, hike the I&M Canal Trail or test yourself at The Forge, a thrilling adventure park with ziplines, climbing walls, rope courses, water sports, and more adrenaline-inducing activities.
Lockport, IL
Your next stop on the Mother Road is Lockport, a Route 66 community with scenic parks, the Will County Historical Museum and Research Center, and a bustling downtown filled with locally-owned shops and restaurants. Snap the perfect road trip photo at the Route 66 Community Shield Monument. Before you get back on the road, stop at Krema Coffee Roasters for craft coffees and sweet treats to energize your trip.
204 N Ottawa St, Joliet, IL 60432
Start your Joliet adventure by learning about the rich history of the Joliet area and the importance that the I&M Canal and Route 66 played in shaping the city.
1125 Collins St, Joliet, IL 60432
Beyond the foreboding walls, take a tour of the iconic gothic architecture, explore the abandoned buildings, and hear tales of some of the most notorious residents.
102 N Chicago St, Joliet, IL 60432
Enjoy a tour of the magnificent Rialto Square Theatre, considered to be one of the ten most beautiful theatres in the nation, followed by concert on the Barton Grande Theatre Pipe Organ.
20 S Eastern Ave, Joliet, IL 60433
Relax over a delicious home cooked meal in one of Joliet's Historical National Landmarks, then explore the mansion on a self-guided tour.
Downtown Joliet & City Square
Now is your chance to wander around downtown Joliet and appreciate the beautiful architecture while visiting some of the one-of-a-kind shops. The new City Square is a public green space that hosts events, live music, free exercise classes, and more.
1990 W Jefferson St, Joliet, IL 60435
A local favorite, enjoy an upscale meal where your group will be welcomed like family. Feast on a limited menu of daily delivered and cut produce and unforgettable sides.
Check in at a local area hotel, there are plenty to choose from! Here are some we recommend.
Day Two: Must-see stops on the way to Pontiac
After a complimentary breakfast at the hotel, set out for great adventures and unforgettable stops along the Mother Road as you make your way to Pontiac, IL — famous for the largest Route 66 Mural in the world.
Midewin National Tallgrass Prairie
30239 IL-53, Wilmington, IL 60481
This is the only place to spot a herd of bison on the Mother Toad! Stop at the Midewin National Tallgrass Prairie Welcome Center to learn about all of the restoration work to this 20,000 acre site that was once the Joliet Army Ammunition Plant, then take a leisurely hike.
110 S Park St Suite C, Wilmington, IL 60481
A ride down Route 66 is incomplete without a picture with one of the road's most famous residents, the 30-foot tall Gemini Giant. Get a group picture and stop inside The Landing Pad for unique Gemini Giant souvenirs, Route 66 memorabilia, and Illinois Made gifts.
222 N Front St, Braidwood, IL 60408
A classic Americana stop for burgers, fries, and shakes as well as memorabilia and photo ops. You may even recognize some famous characters outside the restaurant!
Pontiac Route 66 Museum and Hall of Fame
110 W Howard St, Pontiac, IL 61764
History is alive in this volunteer-run museum. Find memorabilia from the glory days of The Mother Road, artwork by Bob Waldmire, and more Route 66 treasures.
Explore More Pontiac museums & Murals
Downtown Pontiac
Take time to explore the museums in downtown Pontiac, including the Pontiac-Oakland Automotive Museum, the Museum of the Gilding Arts, and the Livingston County War Museum, as well as the over 20+ beautiful murals across the downtown area.
Dinner and a Show at Eagle Performing Arts
319 N Plum St, Pontiac, IL 61764
Cap the night with live entertainment and a catered dinner in the heart of downtown Pontiac.
Check in at a local area hotel, there are plenty to choose from! Here are some we recommend.
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