Masterton is Wairarapa's major population center, and, like Martinborough to the south, it's in a developing wine region. There's not much to do in the town, but it's a handy gateway for hiking in the nearby parks and on the coast. Popular annual events include the Hot Air Balloon Festival in early April and the Golden Shears sheep-shearing competition, usually held the first weekend in March.
State Highway 2 strings together a handful of eye-catching small towns on its way north past the Rimutakas. Farther north on the arrow-straight highway is Greytown, where well-preserved Victorian buildings now filled with cafés and boutiques line the main street. After a few miles more you'll reach Carterton, another small town with a handful of tempting stores—especially Paua World.