The Wairarapa is separated from Wellington by the Rimutaka Range, which means two choices: road or rail. The Remutaka Hill Road (State Highway 2) is a winding drive of about 45 minutes from Upper Hutt to Featherston — scenic but slow, particularly behind trucks. It was briefly closed due to slips, but the new Remutaka Tunnel bypass (opened 2023) has cut the journey considerably. From Wellington's CBD, allow 90 minutes to Martinborough and about two hours to Masterton by road.
By train, the Wairarapa Connection runs from Wellington to Masterton several times daily through the Remutaka Tunnel — the journey takes about 90 minutes and is a more relaxed option if your destination is Masterton or you don't need a car once there. Martinborough and Greytown are not served by rail and require a car or the occasional shuttle.
Wellington Airport is the nearest airport with scheduled services.