GarageCherries
Middletown, DE Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Middletown, Delaware.
7 upcoming events in Middletown
Browse cars for sale in Delaware →Get this weekend's car shows near you, every Thursday
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Upcoming Events in Middletown
Oct
24
Scarecrow Run Car Show
Oct 24, 2026 · Middletown, DE
Fall-themed car show in Middletown, Delaware, featuring classic cars, hot rods, and collector vehicles.
Oct
25
TSD Rally - "There and Back Again"
Oct 25, 2026 · Middletown, DE
Time-Speed-Distance road rally starting in Middletown, Delaware, a driving tour event popular with classic and collector car club members.
Nov
6
2nd Friday Cruise Nights at Grotto Pizza
Nov 6, 2026 · Middletown, DE
Monthly cruise night in the Grotto Pizza parking lot in Middletown, Delaware, bringing out classic cars, hot rods, and collector vehicles.
Jan
8
2nd Friday Cruise Nights at Grotto Pizza
Jan 8, 2027 · Middletown, DE
Monthly cruise night in the Grotto Pizza parking lot in Middletown, Delaware, bringing out classic cars, hot rods, and collector vehicles.
Mar
12
2nd Friday Cruise Nights at Grotto Pizza
Mar 12, 2027 · Middletown, DE
Monthly cruise night in the Grotto Pizza parking lot in Middletown, Delaware, bringing out classic cars, hot rods, and collector vehicles.
Apr
9
2nd Friday Cruise Nights at Grotto Pizza
Apr 9, 2027 · Middletown, DE
Monthly cruise night in the Grotto Pizza parking lot in Middletown, Delaware, bringing out classic cars, hot rods, and collector vehicles.
Jun
11
2nd Friday Cruise Nights at Grotto Pizza
Jun 11, 2027 · Middletown, DE
Monthly cruise night in the Grotto Pizza parking lot in Middletown, Delaware, bringing out classic cars, hot rods, and collector vehicles.
Car Shows in Nearby Cities
Cars for sale near Delaware
1969 Ford Mustang Mach 1 Cobra Jet
2000 Pontiac Trans Am
2003 Mercedes SL-Class SL 500
1976 Triumph TR6
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.