Herbertville to Featherston
You start this day by heading back up the road 8 km to rejoin Route 52 at Wimbledon. Soon after Wimbledon the real work of the day begins as you ascend the steep incline to Ti Tree Point. It can be hard to tell from the elevation charts, in which every hill looks steep; this hill really is steep.
At around the 30 km mark take the turnoff left to stay on Route 52 heading towards Pongaroa (if you get to Weber then you've overshot the turnoff). Here the road becomes more scenic as it flattens out and follows the Akitio River down to Waione, slowly ascending again into Pongaroa (store/tearooms, pub, backpackers, camping at the domain). This is a pleasant, small, rural town; a nice spot to stop for lunch and stock up on food. The store here is the last you'll see till Masterton.
After you leave Pongaroa the road once again begins to climb, but here the gradient is gentler compared to the morning's efforts. Then it's a glorious 5 km descent into Tiraumea. Tiraumea is just a dot on the map; little more than a few houses and a community hall. Here you can camp or backpack at Otapawa Backpacker Lodge, a few kilometres to the right along Haunui Road. Ask locally and you may be allowed to freecamp for the night in the field adjoining the local hall, where there is a toilet and water.
Today you reap the rewards from all of yesterday's climbing. This ride is generally downhill through pleasant farmland. Although 106 km may seem like a stretch you can make very good time along this road, especially if the prevailing northerly wind is behind you.
At Alfredton (camping at the domain) turn left to remain on Route 52, taking you through the Whangaehu Valley into Masterton. Masterton is a large town and has cafés, bike shops, supermarkets and everything else you might need. A good opportunity to replenish your by now dwindling supplies. There are many places to stay within the Wairarapa district, with campgrounds in Masterton, Clareville, Carterton, Greytown, Martinborough, several DOC camps close by, plus some free-camping options (at Lake Wairarapa Reserve just out of Featherston and on the Remutaka Rail Trail). Stop in at the Masterton information office and see what suits you.
Many cyclists choose to head south to the wine growing region of Martinborough, using this as the kick-off point for a tour around the rugged and beautiful Cape Palliser.
At Masterton the road joins up once more with state highway 2. Pleasant riding can be found on the myriad of quiet back-country roads, via which you can dog-leg your way south. The main road between Masterton and Featherston, though, while busy, is safe, being straight, broad, and having ample margin for cyclists.
You should definitely not attempt to cycle highway 2 beyond Featherston over the Remutaka incline. Here the road is narrow, winding and busy. Fortunately there is a great alternative that takes you south into Wellington via the Remutaka Rail Trail...