Cars were lined up along State Street from Orange Street to Redlands Boulevard ready for view by car lovers of all ages.
Many took the time to glance inside their favorites as they walked the strip, taking in the 1960s theme that flooded the area.
"This is exactly the truck my dad drove - paint and everything," remarked one man as he made his way down the street with three friends in tow.
The annual event was the first to kick off the city's June is Jumpin' series to help bring foot traffic and revenue downtown.
Highlander Donald Gabbard received a flier in the mail about the event and decided that it would be a perfect to show off his 1956 Chrysler Imperial.
Gibbard usually attends around 10 car shows a year, he said, mostly to show off his car which is not well known to the West Coast.
During Hollywood's Golden Age of Cinema, the Cadillac was the most filmed and wanted car of the time, he said. But things were different on the East Coast when Imperials used to cruise down the street and would catch the most attention.
"The most frequently asked question I receive is, `What is it,"' Gibbard said. "This is a new car for this area."
Gibbard is the car's third owner. It had been owned by his father, John, and was brought to California from Colorado when he died.
"Having people check out the car makes all the hard work worthwhile," Gibbard said.
Live music by the Tornadoes and a DJ spinning hits from the likes of Elvis and the Beach Boys were added draws, as was alcoholic drinks poured by State Street Winery and Hangar 24 for those 21 and up.
Friday's event was the first time Hangar offered up its custom red ale to the public. The special brew was made to celebrate Redlands' 125th anniversary, and it didn't last long.
In addition to offering up the new flavor, Hangar was also raising funds for the Citrograph Scholarship Fund, which offers scholarships to students entering the University of Redlands and Cal State San Bernardino.
"This is a wonderful event to bring some activity downtown. As you can see, the event has been very popular," said Councilwoman Pat Gilbreath, who volunteered to help out at the Hangar 24 booth.
The Redlands brewery offered up three half barrels for the event - one keg of its Orange Wheat and two kegs of the 125th anniversary ale.
The fun continues downtown on Saturday with the city's Wine, Beer and Music Festival from 4 to 7 p.m. at Ed Hales Park at Fifth and State streets and June 29 with the Food Truck and Brewfest at the Redlands Mall.
Tickets for Saturday's event are $20 per person and can be purchased at several downtown businesses and the city Development Services Office at 210 E. Citrus Ave.
Admission to the food truck festival is $5 per person, and tickets can be purchased at the Development Services Office as well.
To learn more, visit cityofredlands.org or call 909-798-7629.