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Cruise Nights at Willow Creek (South Barrington)
Date: Monday, September 28, 2026 | 5:00 PM - 8:00 PM
Venue: Willow Creek Community Church CARS Ministry, 67 E. Algonquin Rd., South Barrington, IL 60010
Details: A free cruise night hosted by the C.A.R.S. Ministry, open to vintage, classic, custom, muscle and antique cars and trucks. Food and music are provided, with signs on campus directing attendees to the back of Parking Lot F.
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McHenry Cruise Night on Green Street (McHenry)
Date: Mondays, Through October 5, 2026 | 5:00 PM – 8:00 PM
Venue: 1208 N Green St, McHenry, IL 60050
Details: Admission and display parking are free for this regular Monday night cruise-in on historic Green Street. The event brings together a wide variety of vintage automobiles, street machines, hot rods, and collector vehicles. Spectators can stroll the block, admire classic engine builds, and grab dinner or drinks from neighboring downtown McHenry pubs and eateries. It delivers a relaxed, small-town street cruising vibe with plenty of local camaraderie.
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Car & Bike Show at Broken Oar (Port Barrington)
Date: Tuesdays, Through October 3, 2026 | 5:00 PM
Venue: Broken Oar, 614 Rawson Bridge Rd, Port Barrington, IL 60010
Details: Head to Broken Oar every Tuesday night for a free summer Car & Bike Show featuring custom cars, motorcycles, weekly trophies, and a laid-back lakeside atmosphere. Both spectators and vehicle entries are welcome free of charge, and registered exhibitors receive a free coupon to use at the restaurant. Enjoy the cars, scenic views, food, drinks, and weekly awards at this popular Tuesday night gathering.
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Cruise Night Car Show (Bartlett)
Date: Wednesdays, Through September 30, 2026 | 5:00 PM – 8:00 PM
Venue: Bartlett Metra Lot (adjacent to 120 Live), 266 E Railroad Ave, Bartlett, IL 60103
Details: This weekly Wednesday evening cruise night offers free admission and open display parking for all makes, models, and eras. The showcase features vintage muscle, antique trucks, hot rods, and modern exotics lining the commuter lot. Guests can take advantage of indoor/outdoor seating, half-priced pizza specials, cold craft drinks, and music by DJ Arty. It delivers an upbeat, community-centric block party vibe right in downtown Bartlett.
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Al's Hot Dogs Cruise Nights (Long Grove)
Date: Wednesdays,Through September 30 , 2026 | 3:00 PM – 9:00 PM
Venue: Al's Hot Dogs, Long Grove
Details: One of the area's longest-running cruise nights with classic cars, customs, trucks, and motorcycles. Food, music, and a relaxed atmosphere make it a favorite midweek destination for enthusiasts.
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Image source: Felix Greco
Cruisin' Park Ridge (Park Ridge)
Date: Friday, October 2, 2026 | 6:00 PM - 9:00 PM
Venue: Park Ridge Public Library Parking Lot, 20 S. Prospect Ave., Park Ridge, IL 60068
Details: An evening car gathering featuring classic, vintage, and specialty vehicles, with music, food, and community activities. The event is free for spectators.
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RTBE: Halloween Car and Vendor Show (Crystal Lake)
Date: Saturday, October 3, 2026 | 5:00 PM - 9:00 PM
Venue: Ivy Hall Crystal Lake, 501 Pingree Rd., Crystal Lake, IL 60014
Details: A Halloween-themed charity car show featuring cars, costumes, local vendors, music, live glass blowing, and a food truck. All builds are welcome, and costumes and vehicle decorations are encouraged. The vendor market runs from 4–9 PM. The event listing states that it is 21+.
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Classic Cars Cruise Night (Elgin)
Date: Saturdays, Through October 24, 2026 | 4:00 PM – 11:00 PM
Venue: Steak 'n Shake, Elgin
Details: A casual Saturday evening gathering featuring classic cars, customs, muscle cars, and modern performance vehicles. Grab dinner while enjoying an ever-changing lineup of automotive favorites.
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Image source: Old Cars, Strong Hearts
Pearle Vision 2nd Annual Charity Car Show (Crystal Lake)
Date: Sunday, October 4, 2026 | 11:00 AM - 3:00 PM
Venue: Pearle Vision, 4777 Northwest Hwy., Crystal Lake, IL 60014
Details: A free charity car show featuring cars, trucks, motorcycles, and specialty vehicles, with food, music, games, awards, a 50/50 raffle, and the Batmobile. No registration is required for participating vehicles, although staging begins at 9:00 AM and space is limited. Proceeds benefit Northern IL Food Pantry and Guide Dogs of America.
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Grant Township Touch a Truck and Car Show (Ingleside)
Date: Sunday, October 4, 2026 | 10:00 AM - 3:00 PM
Venue: Grant Township Center, 26725 W. Molidor Rd., Ingleside, IL 60041
Details: Part of the annual Fall Festival hosted by Grant Township, Fox Lake and Volo. The event features a Touch a Truck and Car Show along with food and refreshments, vendors and crafters, a petting zoo and pony rides, hay rides, inflatables, pumpkin decorating, and other family activities. Admission is free.
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