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 the first few days of 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 crafts and antiques stores—especially Paua World.