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 LA, stopping and mom and pop diners, roadside attractions, and stores of every variety.  Start your journey with two days along The First Hundred Miles.  

Day One: Exploring Joliet

Start the day at 10am at the Joliet Area Historical Museum to learn about the historical city you will be spending the day exploring. Enjoy two satisfying meals, museum visits, free time and turn in for the night at 7pm.

Joliet area Historical Museum

Joliet Area Historical Museum
Start the morning learning about the rich history of the Joliet Area and the importance that the I&M Canal and Route 66 played in its history.

old joliet prison

Old Joliet Prison Tour
Beyond the forbidden walls, take a tour of the iconic gothic architecture, hear tales of some of the most notorious residents and the intricate history of the grounds.

The Rialto Square Theatre

Rialto Square Theatre
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.

Jacob Henry Mansion

The Jacob Henry Mansion Estate
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
Free time for shopping/wandering after a full day of learning about the area, now is your chance to wander around downtown Joliet and appreciate the beautiful architecture while visiting some of the one-of-a-kind shops.


Al's Steak House
A local favorite, enjoy an upscale meal where your group will be welcomed like family, plan ahead with 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, ending in Pontiac Illinois, famous for the largest Route 66 Mural in the world. Hotel check in at 8pm where your group can reflect on the memories made over the past 48 hours.

Midewin National Tallgrass Prairie

Midewin National Tallgrass Prairie
Enjoy a complimentary breakfast at the host hotel, pack up and get ready for another great day of adventure. Midewin National Tallgrass Prairie Stop in to the Learning Center to hear from staff about all of the work done at the location, then take a leisurely walk around the land. You might see bison roaming the fields, depending on the day.

The Launching Pad/ Gemini Giant

Gemini Giant photo op and frozen snack at The Launching Pad
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 Launching Pad for a frozen ice cream treat!

Lunch at the Polk-A-Dot Drive In
A classic Americana stop for burgers, fries and shakes as well as memorabilia and photo ops, the drive in is one of the most memorable attractions along Illinois Route 66.

Group in front of Route 66 Mural

Pontiac Route 66 Museum and Hall of Fame
History is alive in the museum filled with memorabilia from the glory days of The Mother Road.

Pontiac War Museum GT

Explore the other Pontiac museums and art
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.

The Eagle Performing Arts Center

Dinner and a Show at Eagle Performing Arts
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