The Route 66 Begin Sign: Start your journey at the famous "Route 66 Begin" sign in downtown Chicago, located near the intersection of Adams Street and Michigan Avenue. It’s a perfect spot for photos to mark the start of your Route 66 adventure.
The Art Institute of Chicago: One of the world’s great museums, featuring iconic American art, historical collections, and cultural exhibits. It’s a must-see for any cultural explorer.
Architecture Tour: Take an architecture river tour to see Chicago’s iconic skyscrapers, which reflect the city's rich architectural history and innovation.
Explore the Neighborhoods: Each Chicago neighborhood has its own unique culture and vibe, from the historic South Loop to the vibrant streets of Pilsen, home to murals and Mexican heritage.

Joliet Area Historical Museum: Dive into the area’s rich history, including its role in the development of Route 66. The museum offers exhibits on local history, transportation, and industry.
The Rialto Square Theatre: A beautiful and historic theater where you can enjoy live performances. The architecture alone is worth admiring, with its stunning blend of Italian Renaissance and art deco styles.
Joliet Iron Works Historic Site: Visit this industrial heritage site where Joliet’s steel industry was born. The ruins of the ironworks offer a fascinating glimpse into the city's past.

The Gemini Giant: This iconic "muffler man" stands tall in Wilmington and is a great cultural symbol of the 1950s roadside Americana culture that defines Route 66. It's the perfect photo op and a great example of the kitschy art that blossomed along the route.
Wilmington Historical Society: Learn about the town’s history and its role in Route 66’s development, offering exhibits on early transportation, railroads, and more.

Route 66 Museum: Located inside the Pontiac City Hall, this museum tells the story of the highway’s history and significance to America. It’s an excellent place to get a sense of the cultural impact of Route 66 on small towns across the U.S.
Mural Walk: Pontiac has an impressive collection of murals on the sides of buildings around town, each telling a piece of local and Route 66 history. It's a unique way to explore the culture through art.
The Pontiac-Oakland Automobile Museum: A deep dive into the history of the automobile industry and its relationship to the development of Route 66, showcasing classic cars and automotive culture.

David Davis Mansion: Visit the former home of Illinois Supreme Court Justice David Davis, a stunning mansion that reflects the lifestyle and culture of the mid-19th century. The home is full of historical significance, and the tours give insight into local history.
McLean County Museum of History: This museum offers a look into the cultural and historical aspects of McLean County, including exhibits on the state's role in transportation and the development of Route 66.

Lincoln Depot: This historic site marks the place where Abraham Lincoln gave his farewell speech before heading to Washington, D.C. It’s a deeply cultural spot that connects Route 66 with the nation’s history.
The Old State Capitol: Visit the site where Lincoln served as a legislator. The building itself is rich in political history and offers an excellent view of early Illinois culture.
Postville Courthouse State Historic Site: This courthouse is where Lincoln practiced law and reflects the mid-1800s legal culture and architecture.

Litchfield Museum and Route 66 Welcome Center: This small museum offers a look at life along Route 66 in Illinois, with exhibits on the history of the road, the cars that traveled it, and the towns that lined it.
The Ariston Café: An old Route 66 diner where you can experience local culture and cuisine, perfect for getting a feel of mid-century American dining culture.

The Pink Elephant Antique Mall: A quirky stop that connects you with mid-century Americana. It's a fun place to browse and find vintage Route 66 memorabilia.
The World's Largest Covered Wagon: This roadside attraction is a nod to the cultural importance of travel and the early days of Route 66, blending historical travel with the iconic road.

Glen Carbon Heritage Museum: Explore the cultural history of this small Illinois town, including its ties to the coal mining industry and the local communities along the early Route 66 corridors.
Edwardsville’s Historic Downtown: Stroll through Edwardsville’s charming downtown area with historic buildings, small-town vibes, and a rich connection to the local heritage of the early automotive industry.

The Gateway Arch: If you have time to detour into Missouri, the Gateway Arch is an essential American landmark that symbolizes westward expansion and the history of travel.
Missouri History Museum: Delve into the cultural, historical, and societal shifts in the region, particularly the role that St. Louis played in the development of Route 66 and the expansion of the U.S.

Local Events: Check out local festivals and cultural events in the towns you visit. Route 66 towns often have arts and music festivals that reflect their local culture.
Historical Markers: Look for historical markers along the route that detail significant events in the towns' histories, from railroads to the development of the highway itself.
Eat Local: Try classic diners and small-town restaurants to experience local food culture, including regional favorites like Italian beef sandwiches and deep-dish pizza in Chicago.
Take Your Time: Route 66 isn’t just a road trip; it’s a cultural journey. Spend time in each town, talking to locals and soaking in the small-town charm that makes this route special.

Wandering Souls