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Car Events in Leesburg, FL — 42 Upcoming Events | MotorEvents

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Leesburg, FL

Car Events in Leesburg, FL

42 upcoming events

Event Categories

Cars & Coffee(26)Car Shows(16)

Leesburg Main Street Car Show

Sat, Sep 12, 2026

Leesburg Main Street Car Show

Leesburg, FL

Street Dreams Cruising

Sat, Sep 12, 2026

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Nearby Cities

Kissimmee, FL (230)Naples, FL (196)Tampa, FL (161)Jacksonville, FL (118)Lakeland, FL (113)Clearwater, FL (109)Orlando, FL (100)Venice, FL (100)

·5:00 PM

Street Dreams Cruising

Leesburg, FL

Leesburg Classic Car Show

Sat, Sep 12, 2026 – Sun, Sep 13, 2026·6:00 PM

Leesburg Classic Car Show

Leesburg, FL · Downtown Leesburg

Thu, Sep 17, 2026·5:00 PM

Great Chicago Fire Brewery Third Thursdays Car & Truck Show

Leesburg, FL · 311 W Magnolia St

Cool Cars Under the Stars

Thu, Sep 17, 2026·5:30 PM

Cool Cars Under the Stars

Leesburg, FL

Downtown Leesburg Third Thursdays Car Show

Thu, Sep 24, 2026 – Fri, Sep 25, 2026·5:00 PM

Downtown Leesburg Third Thursdays Car Show

Leesburg, FL

Shifters and Shakes Cruise In

Sat, Sep 26, 2026 – Fri, Sep 25, 2026

Shifters and Shakes Cruise In

Leesburg, FL · Steak ‘n Shake (Leesburg)

Shifters and Shakes Cruise In

Sat, Oct 3, 2026 – Fri, Oct 2, 2026

Shifters and Shakes Cruise In

Leesburg, FL · Steak ‘n Shake (Leesburg)

Shifters and Shakes Cruise In

Sat, Oct 10, 2026 – Fri, Oct 9, 2026

Shifters and Shakes Cruise In

Leesburg, FL · Steak ‘n Shake (Leesburg)

Sat, Oct 10, 2026

Street Dreams Cruising

Leesburg, FL

Leesburg Main Street Car Show

Sat, Oct 10, 2026

Leesburg Main Street Car Show

Leesburg, FL

Leesburg Classic Car Show

Sat, Oct 10, 2026 – Sun, Oct 11, 2026·6:00 PM

Leesburg Classic Car Show

Leesburg, FL · Downtown Leesburg

Cool Cars Under the Stars

Thu, Oct 15, 2026·6:00 PM

Cool Cars Under the Stars

Leesburg, FL

Shifters and Shakes Cruise In

Sat, Oct 17, 2026 – Fri, Oct 16, 2026

Shifters and Shakes Cruise In

Leesburg, FL · Steak ‘n Shake (Leesburg)

Downtown Leesburg Third Thursdays Car Show

Thu, Oct 22, 2026 – Fri, Oct 23, 2026·5:00 PM

Downtown Leesburg Third Thursdays Car Show

Leesburg, FL

Sat, Oct 31, 2026

Gator Harley Davidson’s 5th Saturday Classic Car Show

Leesburg, FL

Leesburg Classic Car Show

Sat, Nov 14, 2026·6:00 PM

Leesburg Classic Car Show

Leesburg, FL · Downtown Leesburg

Cool Cars (& Trucks) Under the Stars

Thu, Nov 19, 2026·6:30 PM

Cool Cars (& Trucks) Under the Stars

Leesburg, FL

Downtown Leesburg Third Thursdays Car Show

Thu, Nov 26, 2026·5:00 PM

Downtown Leesburg Third Thursdays Car Show

Leesburg, FL

Leesburg Classic Car Show

Sat, Dec 12, 2026·6:00 PM

Leesburg Classic Car Show

Leesburg, FL · Downtown Leesburg

Cool Cars (& Trucks) Under the Stars

Thu, Dec 17, 2026·5:30 PM

Cool Cars (& Trucks) Under the Stars

Leesburg, FL

Shifters and Shakes Cruise In

Fri, Dec 18, 2026·7:00 PM

Shifters and Shakes Cruise In

Leesburg, FL · Steak ‘n Shake (Leesburg)

Downtown Leesburg Third Thursdays Car Show

Thu, Dec 24, 2026·5:00 PM

Downtown Leesburg Third Thursdays Car Show

Leesburg, FL

Shifters and Shakes Cruise In

Fri, Jan 8, 2027·7:00 PM

Shifters and Shakes Cruise In

Leesburg, FL · Steak ‘n Shake (Leesburg)

Sanford, FL (90)

Bradenton, FL (87)

Fort Myers, FL (75)