Masterton is Wairarapa's largest town, and it has something for everyone - from shopping, cycle trails and art to great food. It's the perfect place to base yourself and explore the whole region. For families, Queen Elizabeth Park must be your first stop. You'll love the huge playground, flying fox, miniature train, BMX and skate park and walking trails. Wings Over Wairarapa, Balloons Over Wairarapa and Golden Shears are the headline events for Masterton.
Carterton is in the heart of the Wairarapa and makes an excellent central base for exploring the whole region. Carterton is the arts hub of the Wairarapa, home to authors, illustrators and painters. Visit Heart of Arts, an arts, culture and heritage hub showcasing local artists. Two of the town's main attractions are Paua World, an amazing gift shop showcasing Paua shell, and Stonehenge Aotearoa, a working adaptation of the original English Stonehenge. While you're in town, make sure you stop for a pint at Regent 58, a craft beer brewery just behind the shops on the main street. If wine's more your thing, explore the nearby Gladstone wine region. If you love tramping or camping, a trip to the scenic Waiohine Gorgeor Mount Holdsworthshould definitely be on your list.
Towns don't get much prettier than Greytown. It's known for its great food and sophisticated shopping, cute colonial cottages, historic trees and extra-ordinary chocolate! With its small, owner operated shops that are high quality and distinctive, Greytown offers the antithesis of big box shopping or bland and Samey malls you find in many large centers these days. Greytown is the Wairarapa's oldest town, and the site of New Zealand's first Arbor Day. Explore the beautiful Soldiers Memorial Park on Kuratawhiti Street. With a children's playground, tennis court, pools and campground it's a great place to stay or play - and the Greytown Swimming Baths are there too! Within the park are 117 lime trees, planted in 1922 to commemorate the 117 soldiers from the community who died in WW1.
Martinborough is famous for its 20-odd vineyards, most within walking or cycling distance of the village square. It's also packed with colonial charm, and criss-crossed with walking and cycle tracks to explore. The Martinborough fair and Toast Martinborough are the 2 big events that happen yearly. The small town of Martinborough becomes very crowded when either of these events are on which more often than not turns out to be an amazing day.
Featherston is the gateway to the Wairarapa, a welcoming sight as you sweep off the Rimutaka Hill. Amongst the cafes and antique stores of Featherston, you'll find the Fell Locomotive Museum. It houses the only Fell engine in the world, once used on the Rimutaka Railway where its extra traction was specifically designed to cope with the steep incline. See the locomotive and its brake-van up close, and watch films that bring the old days of Wairarapa steam travel to life.
Next door is The Featherston Heritage Museum which tells the story of the historic Featherston military base and its role as a prisoner of war camp in World War II, and provides a background to the nearby Peace Garden, a hauntingly beautiful memorial stand of 68 Japanese cherry blossom trees.