Back before it became the first stop on the Shinkansen line from Tokyo Station (and, for the capital's foreign residents, a key juncture on the dreaded schlep to the immigration office), Shinagawa was known as the first rest stop along the Tokaido Highway from Edo to Kyoto. Started in 1990, this annual festival tries to educate young 'uns in the area's history, and features taiko drumming and parades of people in traditional costumes alongside the less era-specific flea markets and marching bands.
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