With a very early start, you could visit the rugged volcanic landscape of Oni-Oshi-Dashi, about 30-40 minutes drive or bus ride from Karuizawa station. The town is also known for its numerous art museums such as the Sezon Museum of Modern Art, the Hiroshi Senju Museum and the Wakita Museum of Art, and for historical sights like the Shaw Memorial House and the old Mikasa Hotel, a designated important cultural asset now open as a museum. This latter can be visited on the way to or from Shiraito Falls, a graceful waterfall a few kilometers out of town; if you don't want to venture so far for your relaxing scenery, then near the station there's the equally attractive Kumoba Pond.
Immediately south of the station there's the Prince Shopping Plaza, a beautifully landscaped outlet centre with stores from a wide range of fashion brands. A couple of kilometres north there's the fun Kyu-Karuizawa shopping street, where you can load up on souvenirs and locally produced foodstuffs like honeys, jams and liqueurs.
There's a cluster of restaurants and cafes in the Prince Shopping Plaza, and plenty more scattered throughout the town. The main road north of the station has a couple of Chinese restaurants and smaller cafes such as Conversa or, for the very sweet of tooth, the Chocolate Factory. The district south of the station has fewer places, but there's a small friendly steakhouse on the road leading directly south, while a bit further away there's the classy but affordable CoDow and the appealing Cafe Ruhe.
While it's perfectly possible to enjoy Karuizawa as a brisk day-trip from Tokyo, staying a night or two will give you a more leisurely experience, and there's a range of accommodation to suit every budget. Chisun Inn is a business hotel south of the station, while Hoshinoya is a luxury resort complex with beautiful grounds that are home to Harunire Terrace, a shopping area where you can find the Pure Milk Gelato Nagai Farm among other places to shop and eat. For something a little different, the Prince Hotel has some log cabins that are surrounded by greenery but perfectly comfortable; or for a complete getaway, in the mountains outside the town there's the Hotel Green Plaza, with five restaurants, an open-air hot spring and 18-hole golf course.
Quickest and easiest is the bullet train from Tokyo or Ueno stations, which runs every half hour or so, takes about an hour, and costs ¥5910 one way. If you're in less of a hurry, there are buses from Shinagawa station that cost ¥2100 and take around three hours; if you have your own car you can drive there yourself in the same time on the Joshinetsu Highway.
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