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U.S. Route 66 was one of the United State's first continuous stretches of paved highway, and served as a major path for those who migrated west.
"The Mother Road" was established on November 11, 1926, and ultimately stretched 2,448 miles from Chicago to Los Angeles.
From its beginning in Chicago, Route 66 headed southwest to Joliet, Pontiac, Bloomington, Springfield and into Litchfield.
Litchfield began in 1853 with the coming of the Terre Haute, Alton and St. Louis Railroad. Today, it is a city known for its Route 66 icons, expansive lake, and lush landscapes. The city has a population of over 6,000 residents.
Route 66 travelers today enjoy many local attractions, including the Skyview Drive-In Theater ... highly recommended for an evening of fun and nostalgia!
Map showing the approximate route of U.S. Highway 66 in Illinois and the location of Litchfield

Skyview Drive-In TheaterThe Skyview Drive-In Theater in Litchfield continues its long-standing service, bringing its patrons big-screen entertainment. This outdoor movie theater opened in the spring of 1950. The Litchfield Skyview is one of four drive-ins nationwide, that are located on the historic Mother Road, and has been since its opening. It is also the only drive-in with that claim in Illinois. The Litchfield Skyview Drive-in is not only a local tradition, it is a Route 66 hall of fame business. It remains one of several original Route 66 businesses on the Mother Road, in Litchfield. In April of 2023 the Skyview was purchased by Gene and Stephanie Hebenstreit, owners of Victory Lane Ford, and Victory Lane Outdoors. Their son, Alec Hebenstreit, and daughter, Chelsey Semplowski, will be managing the historic venue. The family will be working together to take the Skyview to the next level! The theater operates seasonally, April through mid-October, and offers a grill onsite. The drive-in is located at 1500 N. Historic Route 66 in Litchfield, IL 62056. For more information, opening dates and times, and movie schedule, visit
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Hotels in Litchfield with traveler reviews at TripAdvisor Litchfield restaurant reviews at TripAdvisor Attractions and Things to Do in Litchfield |
Best-Selling Route 66 Books and Maps at our Amazon Store |
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| Route 66 Travel Guide - 202 Amazing Places by Mark Watson ![]() |
Route 66 Full-throttle Adventure Handbook, by Drew Knowles ![]() |
| EZ66 Guide for Travelers (5th Edition) by Jerry McClanahan ![]() |
Rand McNally 2026 Road Atlas Large Scale Spiral Bound ![]() |
About These ProductsThe Route 66 Road Trip website is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn fees by advertising and linking to Amazon.com and affiliated sites. Amazon offers a commission on products sold through their affiliate links. There is no additional cost to you. |
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More Information about Litchfield & Illinois Route 66 |
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VisitLitchfield.com Tourism Bureau City of Litchfield, Illinois website Litchfield Chamber of Commerce Litchfield, Illinois Weather at WeatherUnderground Litchfield Travel Guide at TripAdvisor: Hotels & More |
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