Cruisin' Through the Century: Downtown Bloomington's Route 66 Centennial Celebration
Schedule
Fri, 05 Jun, 2026 at 05:00 pm to Sat, 06 Jun, 2026 at 10:00 pm
UTC-05:00Location
Downtown Bloomington | Bloomington, IL
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We are celebrating 100 years of Route 66 in Downtown Bloomington!June 5 & 6, 2026 | 6pm - 10pm | Downtown Bloomington
2026 marks a once-in-a-century road trip - the 100th anniversary of the iconic Route 66 and McLean County is kicking the celebration into high gear. From May through September, each of our Route 66 communities (Bloomington, Normal, Lexington, Towanda, Chenoa, McLean, Funks Grove, and Shirley) will be fueling up the fun with unique activations, interactive experiences, and photo-worthy stops that celebrate the history, culture, and community of the legendary Mother Road right here in our backyard.
The Cruisin’ Through the Century weekend is your chance to shift gears and step back in time, as each town hosts a themed celebration representing a different decade of road-trip culture. It’s a full-throttle, two-day journey through music, style, and nostalgia - no GPS required.
MAKE YOUR MAIN STOP: DOWNTOWN BLOOMINGTON - JUNE 5 & 6
If you only make one stop along the route… this is the one to circle, star, and double-underline.
Starting JUNE 5:
Join us Downtown for June First Friday with Route 66 and 1960's themes throughout participating businesses from 5pm to 8pm!
JUNE 6:
Bloomington is turning up the volume and cruising straight into the spotlight with a Route 66 themed Saturdays on the Square you won’t want to miss. On June 6, Downtown Bloomington becomes the ultimate pit stop for 1960s vibes, headlined by Motown Nation bringing the soulful soundtrack of the decade to life.
Expect a Downtown experience that’s firing on all cylinders:
🎶 Live Motown hits that’ll have you dancing in the street (literally)
🚘 1960s car show packed with classic chrome and vintage cool
👨👩👧👦 Kids Zone for the next generation of road trippers
🍔 Local eats + community vendors lining the Square
👗 1960s costume contest (bring your best retro look)
🌟 Celebration of iconic Route 66 community members
🎉 A BIG surprise you’ll have to see to believe
…and plenty more to keep the good times rolling
FOLLOW ALONG FOR MORE!
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Where is it happening?
Downtown Bloomington, 205 N Main St, Bloomington, IL 61701-3929, United StatesEvent Location & Nearby Stays:
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