Route 66: Plan A Trip Through AmericA’s Main Street
There's something magical about Route 66 that transcends mere asphalt and highway markers. This legendary stretch of road represents more than just a means of transportation from Chicago to Santa Monica – it's a journey through the heart and soul of America itself. If you’re local to Lemont or the Chicago area, you’ve probably seen tourists stopping at the legendary sign across from The Art Institute of Chicago on Jackson and Michigan (you may even have your own). What better way to mark life's most precious milestones than by hitting the road on the Mother Road and finding a small town, Lemont, in the southeast suburbs that represents it all?
The Birth of an American Icon
Route 66 officially came to life on November 11, 1926, stretching from Chicago, Illinois, to Santa Monica, California. The eastern terminus originally began at 48th Street and Ogden Avenue in Cicero, but was moved into downtown Chicago in 1931 to Jackson Street and Michigan Avenue in Grant Park – making Chicago the true starting point of America's most famous highway.
Historic Route 66 Start Sign in Downtown Chicago
The route's early history in Illinois is particularly fascinating. Initially, Route 66 followed the old Illinois State Highway 4, which had been completely paved by 1923. This original alignment took travelers through Lemont and Lockport as a "temporary Route 66" while the main western alignment through Romeoville was being constructed. By 1928, the new straighter route was completed, avoiding the urban crossings and sharp curves of the original path. While no longer included on the official route, Lemont Downtown remains as one of the original towns along the historic highway.
During the Great Depression, Route 66 earned the nickname "The Mother Road" as it carried hundreds of thousands of Americans westward in search of work and hope. In the post-World War II boom, it transformed into the ultimate symbol of freedom and adventure, lined with quirky motels, classic diners, and roadside attractions.
Though officially decommissioned in 1985, Route 66 refused to fade into history. Today, roughly 85% of the original route can still be driven, preserved as a National Scenic Byway that continues to capture imaginations worldwide.
Why Route 66 Makes Every Milestone More Meaningful
Celebrating Your 66th Birthday on Route 66: There's no more fitting way to celebrate this milestone than embracing the freedom and adventure that defined an entire generation. Many travelers plan their 66th birthday specifically around a Route 66 journey, creating once-in-a-lifetime memories while exploring vintage diners and classic Americana.
Anniversary Adventures: Route 66 offers couples a chance to reconnect away from daily distractions. Whether celebrating your first anniversary or your golden one, the road provides intimate moments – watching sunsets over the Painted Desert, sharing milkshakes at 1950s-style diners, or dancing to oldies at retro motels. Couples who stop in Lemont often enjoy a slow day of antiquing and dining at restaurants or diving into adventure at The Forge: Lemont Quarries.
Multi-Generational Family Vacations:. Grandparents share stories while kids discover life before smartphones was pretty amazing. The route offers something for everyone: vintage car museums, antique shops, quirky roadside attractions, and nostalgic diners where families can gather and actually talk.
Hot Tip: Pick out a map and highlight the current and original route. See who is able to still follow a map to navigate your way through the Illinois portion.
The Perfect Retirement Send-Off: After decades of deadlines and commutes, what's more liberating than hitting the open road? Route 66 offers the ultimate gift of unhurried exploration – you can spend three days or three weeks, finally having the luxury of time to truly see America.
Lemont Downtown | Photo by Molly Hebda Photography
Make a Stop at One of the Original Towns: Lemont Downtown
Just southwest of Chicago, Lemont offers one of the best family-friendly detours along the entire route – and it holds a special place in Route 66 history. Lemont was actually part of the original Route 66 alignment! When the highway was first established in 1926, it followed the old Illinois State Highway 4 through Lemont and Lockport as "temporary Route 66" before the straighter western route was completed in 1928.
This historic connection makes Lemont Downtown more than just a detour – it's a genuine piece of Route 66 heritage. The beautifully preserved historic district features tree-lined streets, historic limestone buildings, and an eclectic mix of shops, family-owned restaurants, and unique boutiques that capture the authentic small-town spirit that originally defined the Mother Road.
Families will love the Lemont Area Historical Society Museum and the nearby Illinois & Michigan Canal Trail, perfect for scenic walks and bike rides. The downtown area regularly hosts family-friendly festivals, adventure days at The Forge: Lemont Quarries, or dining at one of the amazing restaurants around town (You can’t go wrong with any of them!)
Ghostly Legends and Haunting History
Route 66 isn't just famous for its roadside attractions and diners – it's also home to some of America's most intriguing ghost stories and legends. The highway's rich history has left behind more than just memories; it's created a tapestry of supernatural tales that add another layer of mystique to the Mother Road experience.
Right at Route 66's Chicago origins, the highway runs past the former site of the infamous Schuttler Mansion – a multi-millionaire's palace that stood empty and possibly haunted for decades after its owner's death. In the southwest Chicago suburbs, Archer Avenue (which often served as a construction detour for early Route 66) is famous for sightings of the ghostly Resurrection Mary, who has been known to ask unsuspecting travelers for a ride.
These ghostly stories remind us that Route 66 isn't just about the destinations – it's about the countless stories, both seen and unseen, that have accumulated along America's Main Street over nearly a century of travelers.
Make Your Route 66 Celebration Unforgettable
The beauty of Route 66 lies in the freedom to create your own adventure. Whether planning a weekend getaway or cross-country odyssey, start your journey by exploring the original alignment through historic Lemont, embrace the kitsch of roadside attractions, stay in historic motels, eat at local diners, and talk to locals who are passionate about preserving the road's history. Don't forget to keep an eye out for the ghostly legends that add mystery to your travels!
Get your kicks on Route 66, and discover why America's Main Street – complete with its hidden history and haunting mysteries – remains the perfect backdrop for life's most meaningful celebrations.
