Located on the southern tip of North Island one hour from Wellington, Greytown is the oldest town in the Wairarapa region of New Zealand. You can feel some of that history in the restored Victorian buildings that line the main street of this rural town, which is surrounded by wineries offering a selection of cabernet sauvignon, pinot gris, riesling, and other popular varieties. Strolling through Greyton’s charming storefronts and eateries, you’ll find shops focused on the art of the craft, such as a handmade bicycle outlet and sustainable fashion boutiques, and many of the restaurants source fresh ingredients from nearby farms.

Greytown was the first inland town to be founded in New Zealand in 1854. You can learn about its rich past as the region’s largest market center during a visit to the Cobblestones Museum. The pastoral landscape around the town is popular for birdwatching, hiking, biking, and simply strolling through groves of trees. Greytown runs a historic tree register that catalogs and protects English Oaks and Peruvian Peppercorn, among other species.

The warmest time to visit Greytown is in the summer months (December through March), when the streets fill up with shoppers browsing the town’s independent boutiques in the settled sunshine. The cooler days of autumn mark wine harvest time in the surrounding Wairarapa wine region, while winter can bring frosty temperatures, so you’ll need warm clothing. Springtime (September through November) is marked by mild temperatures and fewer visitors, and you should be prepared for strong winds coming off the Tararua Range.

One of the most thrilling times to stay in Greytown is during the annual balloon festival held in April, when competitors from all over New Zealand take to the skies in brightly colored and bizarrely shaped hot air balloons. The changing shades along the Greytown Heritage Tree Trail also make a scenic wander in the crisp autumn air.

Soldiers Memorial Park

Soldiers Memorial Park is both a World War I memorial and city park. In 1922, 117 lime trees were planted here to commemorate 117 fallen soldiers. Today, the avenue of lush lime trees is a main draw for photographers. This Greytown park is within walking distance of the main street. It has a playground and plenty of shade, making it a great place for an afternoon picnic.

Cobblestones Museum

The Cobblestones Museum comprises buildings from the 19th and early 20th centuries, which were carefully restored by volunteers. You can visit the fire station, the old Hastwell stables, Wairarapa's first hospital, and a Wesleyan Church here. Experience a school from the 1900s here as well, complete with a cloakroom hung with leather school bags, and classrooms with blackboards and chalk dust.

Greytown-Woodside Trail

If you're seeking stunning views of the Wairarapa countryside, look no further than the three mile Greytown-Woodside Trail. The pathway is ideal for walking and cycling, with no steep inclines, winding its way from the center of Greytown to the Waiohine River, eventually ending up at Woodside railway station.