Every year since 1997, more than 100 cars have left Tokyo on a 680-mile rally paying homage to the famed Italian Mille Miglia road race. Dubbed the “La Festa Mille Miglia,” this rally celebrated its 20th anniversary this year and is considered a “sister event” of the official Mille Miglia. It’s the vintage car heaven you’d expect from a name like that, with a Japanese touch.

1926 Bentley 3L Speed Model

The start and finish point are always the same: the Meiji Jingu Shrine in Harajuku, Tokyo. It’s always usually held around mid-October too so if you want to see a huge parade of classic cars from the 1920s up to 1961 drive through one of the busiest districts in Tokyo, then this is the event to come see.

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October is quite a busy time in Tokyo for car events and the La Festa Mille Miglia is one of the biggest. The drive goes across seven different prefectures in Japan over four days. The route changes every year but they always put the route on their website if anyone wants to see the cars drive through certain places.

It’s actually one of the few classic car events held annually in Tokyo. For as crazy as the tuner and exotic scene is in Japan, there’s very few opportunities or venues for classic car owners and fans to come together. There’s not even an equivalent Concours d’Elegance event in Japan, which is a shame because an event like that would surely draw out some of the hidden classic gems in Japan.

1954 Aston Martin DB2-4
1939 Fiat 6C

According to the organizers of the La Festa Mille Miglia, the event aims to promote the “treasuring of antiques,” and “remaining youthful at heart.” It’s also a great way of sharing classic cars with a large chunk of Japan.

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Unlike the Ferrari rally, most of the driving here is done on normal roads through small towns, countryside villages and large cities. As well as promoting classic cars, the La Festa Mille Miglia is held to celebrate the special friendship between Japan and Italy.

I can’t say I’m an expert on every single car in this rally, but the superstars are easy to spot. I also would love to join them on one of these rallies one day, because it must be quite the experience.

1964 Ferrari 330GT 2+2

I mean, how many chances are there to see one Toyota 2000GT on the road, let alone two? Other highlights included a Fiat 6C, Lagonda V12, Bugatti T35B, Porsche 356 Speedster, Mercedes 190SL, Ferrari 330GT 2+2, and a Maserati Mistral Spyder.

As well as the cars on the rally there were several support and crew cars including a fleet of new Porsches, Lexus, and Alfa Romeo cars, as well as vans full of mechanics and tools for service at the end of every day of driving.

1968 Toyota 2000GT

For the last three years I’ve only spectated from the sidelines along with everyone else. Previously I’ve seen the cars pass through the first checkpoint at the Daikanyama T-Site and watched them leave the starting point at Meiji Shrine. This year I waited for the cars to pass through their last checkpoint at Nihombashi in central Tokyo before they crossed the finish line at the Meiji Shrine.

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The cars were expected to pass through at around 4 p.m. but by this time it was getting quite dark and wet. There were still people lined up in front of the Mitsukoshi department store where the final stamp was given to the participants.

1958 Chevrolet Corvette

As great as it was to see the cars leave Meiji Shrine on the first day, it was also pretty special seeing them come back to Tokyo after what would’ve been a challenging four days. Also, seeing 100 or so classic cars drive through one of Tokyo’s most modern business districts was quite a special sight.

1958 Porsche 356 A Convertible D

Even in a city like Tokyo, seeing cars like these is a rare spectacle and I’m glad an event like this exists. With other events such as the Automobile Council classic car show, the Asama Hill Climb, and Suzuka Sound of Engine, events for classic cars are far and few in between.

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As great as it is to see them in pristine condition at a museum, there’s also a place for seeing and hearing these classics bust to life on the road.

1927 Bugatti T35B
1952 Fiat 8V Zagato
1959 MG A
1928 Bugatti T40
1939 Lagonda V12
1958 AC Aceca
1947 Fiat Stanguellini 1100 Sport
1951 Jaguar XK120
1953 Bandini 750 Sport
1947 Fiat Farina MM
1957 Alfa Romeo Giulietta 750D
1952 Triumph TR2
1948 Cisitalia 204
1947 Fiat Gilco Stanguellini 1100 Sport MM
1927 Austin Seven
1953 Porsche 356 Pre-A
1965 Maserati Mistral Spyder
1934 Riley 12/4 Sports Special
1961 Porsche 356B Super 90 Karmann Body
1959 Alfa Romeo Giulietta Sprint Veloce
1932 MG C Type
1958 Alfa Romeo Giuletta Spider
1958 Fiat Abarth 750 GT Zagato
1958 Mercedes-Benz 190SL
1935 Fiat 508 S
1959 Lancia Flaminia Sport Zagato
1957 Porsche 356 A Speedster
1959 Lancia Appia Zagato