Learn more about the Upcoming Byway Centennial Celebration & the Illinois Route 66 Experience at the State Fairgrounds
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Featured Illinois Route 66 Scenic Byway Member
Litchfield, IL
The Sky View Drive-In opened in the spring of 1951 and has been in seasonal operation since. It is the last remaining original operating drive-in theatre on Route 66 in Illinois. Inducted, in 1998, into the Route 66 Association of Illinois Hall of Fame.
Rt 66 Skyview Drive-In Theater
1500 North Historic Route 66
Litchfield, IL 62056
(217) 324-4451
Events on Illinois Route 66
Events
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Route 66 Submerged: A Sunken Road. A Story Resurfaced.
Lake Springfield Marina 17 Waters Edge Blvd, Springfield, IL, United StatesStep aboard Route 66 SUBMERGED, a 45-minute interpretive boat tour on Lake Springfield that reveals a hidden chapter of America’s most iconic highway. Beneath the surface lies a stretch of Springfield’s original Route 66 alignment, submerged when Sugar Creek was dammed in 1933. Guided by local storytellers this immersive journey blends history, nature, and narrative—offering…
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Dwight Harvest Days/Basset Bash & Waddle
Downtown Dwight 417 W. Waupansie, Dwight, IL, United StatesRed, White, and Blue-Hundred Fifty Years! Welcome to Dwight Harvest Days, where we're combining our usual start-of-Fall fun with a special celebration of 250 years since the United States declared its independence. Join us September 17-20, 2026, for a weekend filled with carnival rides, a Basset Waddle, live entertainment, and plenty of patriotic fun in…
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Bicycle Illinois Route 66 Ride
Illinois Route 66 IL, United StatesBicycle Illinois is excited to introduce the Route 66 Ride, a new week-long cycling tour traveling from the St. Louis area to Chicagoland along the legendary Old Route 66. This tour is still in development, and registration is not yet open, but riders are encouraged to stay tuned for updates as plans continue to progress.…
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GTOAA All Pontiac Regional Car Cruise & Show
Pontiac-Oakland Automobile Museum 205 N. Mill Street, Pontiac, IL, United StatesCruise into Pontiac for the GTOAA All Pontiac Car Cruise and Show on September 19 – 20, 2026! Hosted by the Heart of Illinois GTO Club and Gateway GTO Club, the show will take place from 9:00AM–5:00PM Saturday and Sunday outside the Pontiac-Oakland Auto Museum. This Centennial Certified Event will be a special celebration of…
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15th Annual All Pontiac (Pontiacs in Pontiac) Car Show
Pontiac-Oakland Automobile Museum 205 N. Mill Street, Pontiac, IL, United StatesThe 15th Annual All Pontiac Car Show in Pontiac, Illinois is revving up for a double Centennial celebration! In 2026, both Route 66 and the Pontiac automobile brand mark 100 years—and this car show honors them both in one exciting weekend. The main event takes place Sunday, September 20, 2026, with a full lineup of…