Oiwake sits at the junction of the Nakasendo highway and the Hokkoku Kaido, one of the branching points in Edo Japan's road network where travelers stopped to decide which direction to continue. The post town that served this traffic was prosperous and lively; the folk song that developed here — the Oiwake-bushi, originally sung by the horse drivers who worked the road — spread widely enough to influence regional music across central Japan. The September festival recreates something of this history: period-costumed processions, horses, and performances of the Oiwake-bushi in a setting that preserves more of the original post town character than most Nakasendo sites. The song itself is worth knowing — a kind of measured melancholy that suits a place where roads diverge and travelers made decisions. Oiwake is administratively part of Karuizawa, which is famous as a summer resort. The post town is a different place entirely — older, less curated, carrying a different kind of atmosphere. Finding it requires knowing it is there, which is a prerequisite for everything worth finding.