Old Town, the entertainment district on Highway 192 in Kissimmee, holds a Classic Car Show and Cruise every Saturday. It is an afternoon-into-evening cruise-in rather than a morning cars and coffee. Old Town’s events page gives the start time as 1pm, registration from 1pm to 7:30pm, and the cruise kick-off at 8:30pm.
Old Town says the Saturday cruise has run for nearly 35 years and “can have up to 250 cruisers.”
Which cars qualify
The Saturday show is for vehicles manufactured before 1985, “like hot rods, classics and antiques.” Old Town adds, in brackets, “No Patina Allowed.”
When to arrive
Show cars register on-site between 1pm and 7:30pm, and the cruise along the brick streets starts at 8:30pm. Old Town publishes no end time for the cruise. Its shops and restaurants are open until 11pm on Fridays and Saturdays.
Where to park
Cruisers enter from Highway 192 at the east entrance, beneath the jukebox signs. Event staff meet each car and arrange a security escort to its spot. Old Town is clear that “only registered cars are permitted to drive on the bricks.”
For spectators, Old Town’s parking page says it offers free parking in lots behind each building. The same page describes a larger lot next door, off Florida Plaza Boulevard and across from Fun Spot, with over 650 spaces, where parking is $11 plus tax and fees per car. Unpaid cars there are towed.
What it costs
Old Town publishes no fee for the Saturday show. Its Friday listing says car owners and spectators can enjoy that show and cruise “at no cost.” Each cruise on a Friday or Saturday enters the car in a monthly draw: one cruiser wins $1,000 on the last Friday of the month and another on the last Saturday.
The rest of the week
Saturday is not the only car night. Old Town runs a Friday Night Muscle Car Show and Cruise from 3pm, for muscle cars from 1964 on and older hot rods and classics up to 1985, with the same 8:30pm cruise. It also lists a Wednesday bike night and an Import Car Show on the first Sunday of each month. Its annual list includes a Classic Car Show and Cruise anniversary every March and VetteFest on the first Saturday in October.
What time is the Old Town car cruise on Saturday?
Registration runs 1pm to 7:30pm and the cruise starts at 8:30pm, per Old Town.
What cars can enter?
Vehicles made before 1985, such as hot rods, classics and antiques. Old Town says no patina is allowed.
Is it free?
Old Town publishes no fee for the Saturday show. Parking in the lots behind the buildings is free; the large lot next door is $11 plus tax and fees.
How do I get my car in?
Arrive from Highway 192 at the east entrance under the jukebox signs. Staff register the car and escort it to a spot.
Is there a modern car night?
The Friday Muscle Car Show takes cars from 1964 on, up to 1985, plus older hot rods and classics. Old Town also lists an Import Car Show on the first Sunday of the month.
Is it running this weekend?
Yes, if it is a Saturday. Old Town lists the Classic Car Show and Cruise every week.
- Source: Old Town, Car Shows and Events page, read 1 November 2026
- Source: Old Town, Parking page, read 1 November 2026
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